EP 021 - Masterclass on Strategy with Alex Small, Head of Strategy & Operations, Central at Stripe

Rohit: Hey Alex, welcome to the pod. Really glad to have you here. Alex Small: Hey, thank you. Great to be here. Rohit: Why don't we start with the question, who is Alex Small? Alex Small: All right. Uh, yeah, that's, that's a big question, but I'll see what I can do to answer it concisely. Um, so, uh, I have a background in finance first and foremost, uh, you know, that of course, uh, it's part of why I'm on this podcast. Um, I worked for a few major tech companies in my career. I started out, uh, at a company called Zendesk. Many of you probably know it. And then I worked for a company called ClickUp, uh, after leaving Zendesk after six and a half years. And then most recently I've continued my finance journey at Stripe, who again, many of you probably know. In my spare time, I like to focus on investing, making businesses, starting businesses. And also when I have time, spending time with my family and also traveling. Rohit: Wow, that's quite a handful. I don't know many people who do investing and starting businesses in their spare time. But why don't we, with that introduction, dig a little bit more into your background? Can we learn about your journey and understand the key milestones that have shaped your career so far? Alex Small: Yeah, great. Yeah, I'd be happy to. So, yeah, I think my journey, if I think back to, you know, even just back in school, right, before I actually graduated and got into the career of finance, I was always interested in business and economics. I was the kind of person that was requesting books about investing for, I don't know, my, you know, 12th birthday or something like that. I was very excited about the idea of dividends. from a very young age and started dabbling with stocks and talking to my family about investing even when I was very much still a child. Then in school, I wasn't really sure what I wanted to do and probably should have been more aware that that's my calling and something I should have been involved in early on, but I also considered a few other things, physics, going into the medical field, but eventually landed on business management economics as a college major. went to UC Santa Cruz for that, and then kind of stumbled into FP&A. My dad was actually in IT, and so he was working for a company called Lithium Technologies, which I didn't even mention earlier. I was only there for about a year and a half, so it was pretty brief stint. But he got me an internship there in financial planning and analysis, which all of you probably know, much like strategic finance, finance and strategy, similar type of work. And I loved it. It was just like a really fortunate thing that I landed in that because it was right at this intersection of all the things that I most enjoy. Like I'm a relatively social person. I enjoy working on things that allow me to interact with people and be part of systems of people. But I'm also a very math-oriented and very logic-oriented person. And so, you know, strategic finance or FP&A gave me this opportunity to kind of think about the system. of a business. And it's where I first started to really appreciate the dynamics of how strategy, operations, and finance need to come together to make a business successful. And where I first started to realize that candidly, most people aren't very good at bringing those things together. It's really rare that one person has the skill set to bring together all of those things. And where I learned that I was pretty good at that. I could understand the finance side very well. I enjoyed the operational side of the business, thinking about things are actually executed. And while strategy may not be the first thing that I jumped to in a lot of my thought processes, something that I've become very accustomed to and I think very adept at, and connecting the dots between the three of them has been very easy for me, I think relative to some in their careers. So thinking about the journey of getting there, as I go from that internship in FP&A at Lithium. One of the most formative things that happened to me early in my career was I was put in a system administration role for FP&A. And, you know, again, this is kind of random, you know, it's just, this is what we need from you. You know, you're, you're an intern. You just got converted to full time because you're doing a good job. Uh, one of the things we'd love for you to do is manage system administration for us. And, uh, that was like another opportunity to kind of test a part of my skill set that I didn't know existed, which was to get like really technical. and really map things out in the business using logic, really seeing the structure of how everything interconnects and kind of formulaically tying together different pieces of the business in a very literal sense. And I think it honed my technical skills, helped me learn a lot about like accounting and other things that I honestly hadn't focused much on in my studies in school and gave me this platform to build on as I thought about systems thinking for the business at large through the rest of my career. So fast forward from that role at Lithium, I got a job at Zendesk. As I mentioned, I was there for six and a half years. Started out as a financial analyst and I ended my time at Zendesk six and a half years later as a VP. So I was promoted every, I don't know, eight to 12 months, pretty much reliably throughout my time there. And a lot of that upward trajectory came from just having this ability to connect so many different facets of the business, I believe. and be able to have that systems thinking lens and portfolio lens that gets applied to the broader business. And it was always the case that, you know, when some area of the business was struggling, they would think, you know, let's have Alex be the finance partner. You know, he can go kind of like map things out, help the leader, think about the financial levers, strategic and operational levers, how they all interact with each other and to relate with each other and be able to then, you know, help the decision-making process improve. That culminated in another kind of formative time in my career where I transitioned from being just a finance person to being a true, like on paper, finance and strategy and operations person. I was given a dual role when I was promoted to senior director at Zendesk, which, you know, then kind of held through to my VP role there as well, where I was working with the then COO at Zendesk named Jeff Titterton. who I'm now working with again at Stripe actually, he's the CMO at Stripe now. And the role that I was given was to be his chief of staff and his strategic finance department, we call it finance and strategy there at Zendesk. And so this was, you know, again, like true stepping over the line. You know, you're no longer just the finance person who's kind of, you know, sometimes people would say like in an ivory tower, you know, not really that engaged with the business, looking at the numbers and kind of advising. I was on the other side and people expected me to make that function successful, both in terms of like the people, the organization, also the strategy. And then, you know, similarly on the finance side, being able to connect all of those dots and bring it together to help the business leaders themselves create success out of all of that. So it really could be their right hand. And I thought that was a really Cool role. I love that role because one, it was kind of unique. Not a lot of people get that opportunity to actually be on both sides simultaneously, both kind of a chief of staff and a finance partner. And having that specific intersection of roles gave me visibility and not control, exactly, but some degree of influence over anything that I thought was important across that leader's entire portfolio of teams. And he was a COO, so it was about half the company. It was everything from product, customer support, customer success, and then even, you know, SMB sales, parts of marketing. As it was a wide purview. So it was very interesting, very great learning opportunity. So I'll jump ahead a little bit. Another big kind of growth opportunity and turning point in my career happened at ClickUp. I left for ClickUp because I wanted to do the startup thing. You know, Zendesk was like a great slow and steady kind of role in a way. You know, not for the company is... not a growth company, but it was still a much more mature company. ClickUp was the rocket ship young company with, you know, big IPO prospects. Could potentially be a, you know, multiplied, you know, stock price. And, and a few things happened while I was there. One, the market crashed and so the, you know, stock price aspirations were impacted by that. But I also was able to really explore a lot of other parts of the potential career journey that I hadn't even expected going into it. So the first year there, I was the head of strategic finance for them. But then the second, I moved into a series of operations roles, really like a cascading of increasing operations purview. First, I took on the customer support team and the customer success team as I handed off the finance team. But then I also took on their Philippines build out as well as the global partnerships, strategic partnerships organization. So it ended up being a role over now hundreds of people managing functions that I had supported throughout my career from a finance perspective and a chief of staff perspective, but not anything that I had actually come up doing. I was not a customer support person. or a customer experience person or a partnerships person or a global operations overseas operator. I'd never actually done any of those things directly myself, just kind of tangentially through finance. So incredible learning opportunity. I was also managing a team of executives. And so there was a lot of seniority and just an overall purview. And that was great, but then Jeff came calling and Stripe came calling and I was enticed over to Stripe. because it was an opportunity to work for, you know, what really I think is, and I think many people would agree, is one of the best companies in the world. Like Stripe just has that reputation for being of a caliber that is up there with the Metas and the Googles and the Amazons of the world. And I think I wasn't wrong to believe that was the case. I mean, there's just some really brilliant folks at Stripe. And so I've been enjoying my time there and the opportunity to... learn from some of like truly the best and brightest, not that the rest of the companies weren't full of, you know, brilliant people, about how to, you know, better run businesses. And there I'm in another kind of intersection of all things, kind of role, managing strategy operations and working very closely with finance to pull things together. I'll pause there. It's a lot. So let me know where you'd like to dive in. Rohit: Now super, super exciting journey that sounds like. There's a lot to unpack, but I want to go back and understand a little more about what do you mean by systems administrator at lithium? What exactly did you do? Alex Small: Yeah. Uh, great question. So I, I was an administrator for our planning tool. Uh, so many folks who listen to this podcast are probably familiar with tools like adaptive planning, uh, tools like Hyperion PBCS, um, and there's a number of other tools out there and a plan, et cetera. So at lithium, I was just an administrator for, uh, the adaptive planning tool. And then I moved over to Zendesk. was system administrator for their adaptive planning tool and was responsible for then implementing Hyperion PBCS, which really, I didn't mention that earlier, but that was an even further continuation of that journey in a direction I did not expect to go because you have to basically code. I mean, it's proprietary coding that you have to do for Hyperion PBCS to make it an effective platform. It's 100% based on its own proprietary coding. There's almost nothing that's out of the box. Rohit: Very interesting. And so it's basically designing the system, actual software system, which will do your financial planning and analysis that suits your business the best, right? And thereby you are saying the thinking, and systems thinking around what is going to like, X plus Y plus Z is going to lead to ABC. All of that and backing and making sure you are thinking maybe two years, five years, 10 years down the line and able to bring that all in. Is that kind of what you really mean by systems thinking or is there much more to it? Alex Small: Yeah, I'd say that's generally right. Yeah, it really can be as big as you want it to be, building out a planning tool. There are a lot of people out there who implement systems like this and they set it up so that you do a bunch of your work in Excel and then you just dump the final numbers into the planning tool. And it is then kind of like a system of record and you can use it for reporting later. That I would say is table stakes. That's the minimum capability of the tool that you capture your forecasts in there, and you can use it for reporting, and you do a little bit of reporting automation. I was always a fan of taking it multiple levels beyond that. So the first level above that, I would say, is using more of the automation capabilities. So it's using it as an actual financial modeling tool, not just as a financial data capture or reporting repository. So examples of that are capacity models. You could plan out how many sales headcount you need for the business by building the calculations into the tool so that all you have to do is input, hey, we want this bookings number and we need this productivity per rep. And now it's going to tell you how many reps you need based on a bunch of other things like ramp times and budget and all of those other parameters. You also could do the same thing for a revenue model, you know, and break down all the different products, all the levers that influence product sales and better understand how you're going to build up to your sales and revenue numbers. Um, so that's kind of level one. I think level two is, uh, building, you know, more of the long range elements of all of that, which you're starting to hit on, uh, and, uh, that is incredibly important to long range planning. It's incredibly important to rolling forecasts, uh, that go beyond 12 months effective and don't take an enormous amount of time from the team to recreate. And then maybe level three, which is kind of like a foundational element beneath the other two is that systems thinking lens. So this idea of it's not just, okay, you have a revenue model, you have a sales model, you've got a long range plan and those just exist in the tool. Or the reporting and the actuals that you manually load just exists in the tool. it is interconnecting all of these things. So that not only are you inputting productivity numbers and bookings targets to get sales reps, and then putting in, let's say utilization targets and bookings targets to get professional services implementation headcount, but then you're also layering on other elements that actually look at all of these other things. Like maybe you're also putting in the location of all of those headcounts. And so you can calculate the tax burden for your... different subsidiaries based on the amount of cost that is flowing through each of the individual subsidiaries related to those headcounts. Or maybe it's your G&A headcount. For example, you need a certain ratio of finance people to the rest of the company, so you have all that other headcount in there. And then you can have a one to 100 ratio, let's say, of finance, strategic finance folks related to all of them. So there's just an enormous amount of capability and a number of other things you can do like T&E calculator, per head T&E dollars, there's just anything you can dream of. So it's almost like a palette to be creative on. And I found all of that fun, the creativity piece, the system building piece, and then the opportunity to use this as like a reason to understand the entire business. Rohit: Very cool. You mentioned at Zendesk, of course, you got promoted every 8 to 12 months. And that's just staggering to be able to do that, not once, not twice, not thrice, but multiple times over in a period of what, almost 6, 7 years that you were there, right? Alex Small: Yep, six and a half, yeah. Rohit: Unpack the secret for us. How did you do that beyond maybe working 60, 70 hours a week? Or maybe you didn't. Alex Small: Yeah. So yeah, no, I definitely did work 60 or 70 hours a week. So that's part of it. You know, one of the biggest secrets I always tell people about my career trajectory is, well, if you work twice as hard, you get promoted twice as fast. You know, so there's definitely an element to that. But I would add a few other things. So one is you have to have You know, you almost think of it, if you take like the founder kind of mindset or a business owner mindset, you need your competitive advantage because ultimately being promoted and taking on new roles, whether it is, you know, taking a role, someone left, taking a role that's being created for you, or just getting promoted and whatever your line of work is and not really displacing anyone else or replacing anyone else. You're still competing. You know, there's always someone else. You know, the manager mindset is, can I hire someone better externally at this level? You know, if Alex is a manager and he wants to get promoted to senior manager, you know, could I hire a better senior manager than Alex? If the answer is no, then they should promote you and you can tell them that, you know, like that's a narrative that you can use around why you should be promoted and the right kind of pragmatic finance people will, you know, support you with that narrative if they really believe it. And so how do you create a competitive advantage for yourself? Well, it comes down to a few things. Like one is, uh, be, be the most, like have the best marketing. Right. So you got to be the best, uh, Advocator for yourself. Uh, that means, you know, asking for promotion. It means making sure people are aware when you've done something that, you know, warrants recognition. Um, but frankly, I would say that, you know, while I have gotten good at managing perceptions, I do not think that I manage perceptions. above average, more than most people. I think that's table stakes. It's something you have to have to be successful in getting promoted and in appearing successful enough to be promoted, but it is not something that I overly relied on, I believe. So just something to keep in mind. Another thing that was really helpful for me was really solving business partner problems. So as a strategic finance partner, an FP&A partner, most managers will gauge your performance based on what your business partners say about you. I mean, for me, and I think for many other leaders in the space, that's the number one thing they look at for their team members who are business partners is, does your business partner think you should be promoted? Are they going to be really upset if you left because you didn't get promoted? And could they hire someone better in your position at the level that you're trying to get promoted to? And so I always formed incredibly close relationships with my business partners. And biggest secret to my success. Just taking a couple of examples of what that looked like. So there was one customer support leader I worked with relatively early on in my career. And she was one of the first to see me as like a true chief of staff and even talk to me about wanting me to become a chief of staff for her, which is funny, because then I ultimately ended up becoming chief of staff for a different leader as well as finance partner. And also he was managing the customer support organization. And then I later managed customer support, you know, so there's like a common theme there. But a big part of what allowed me to be successful was caring about learning her business area as well or better than she knew her business area. Like that's the, I think, simplest and most comprehensive way to summarize getting to be that level of partner for that type of executive. You have to be able to be in a conversation with her and say, you know, your business, you know, better than I do, but I know it. very well, and I know parts of it even better than you do. And I know finance very well. And I know how to use that financial knowledge to advise you on how to run your business in a way that you wouldn't have otherwise been able to figure out. Like that is ultimately the value proposition of a strategic finance business partner for a leader. And so again, just taking an example of how that actually plays out. Most of it was around headcount planning. So I ultimately became known for her as well as tons of other leaders that I partnered with. as the person that you go to understand like how many support reps do I need. It was actually not simple, you know, you can think like, you throw out some utilization and productivity numbers, you know, your ticket counts. Uh, you should be able to calculate the number of headcount you need, right? Like kind of, but to do it really well, you actually need to think about ramp times. You need to think about seasonality of tickets. You need to think about ticket types. There's different channels. You think about specializations, seniority, you have to think about location. You're gonna do this in the Philippines, is there a different productivity, but there's also a different cost. You gotta think about budget, budget targets. There's a whole ecosystem of things that come together to help you identify what the right number of target hires is in any particular time period. And so, being on top of all of that and working closely with our leaders and just helping them be better and make the right decisions. And then ultimately look good to their bosses and the rest of the company. Like, hey, I drove down my spend numbers and also hit my operational goals because I was hiring the right amount of people and they were executing well. And what they don't often say, but what they're thinking is I was able to do that because I had a great finance partner who helped me know exactly how many headcounts to bring on board to be able to hit my goals without exceeding the budget targets that I should be at. So that I think is... one of the most illustrative examples, and I repeated that with many other leaders throughout my time. I'll just add one other thing that I think was really important, which is getting a variety of experiences. Because to that systems thinking and sort of mapping mindset points that I was trying to make earlier, if you work in a number of different roles and a number of different functions and have a number of different business partners, work at a number of different companies, you're getting exposure to a lot of different things that start to build your intuition. You know, if you just work on the same thing over and over again, I think there's a tendency to get really good at following those motions. And, you know, you can do that process in your sleep and there's advantages to that. But you don't have the intuition of, well, there's this other thing I've seen done elsewhere, which actually could be better or the way this function operates. You know, it might be negatively impacted by the things that we're doing here. And so we should actually do it slightly differently to build better cohesion with that team. And then you can build a relationship in that case or whatever that actually ends up improving everybody's success, parents' success and actual success. So there's just countless examples of how having that variety of experience can be valid. Rohit: Makes a ton of sense. Were you ever perceived as sharp elbowing other people? Alex Small: That's a good question too. I would say to be very successful in business, there has to be an element of, you know, sharp elbows. What, what is funny is I think I'm perceived as having sharp elbows with my peers. And so maybe that is part of, uh, you know, my success and, you know, that, that also, uh, is an example definitely of me having sharp elbows. I don't have sharp elbows with. my leaders, the folks that I'm rolling up to or that are above me in the hierarchy of the organization. And I don't with my team. I tend to be very close with my team. I'm very high on psychological safety as a concept. I enjoy my team feeling like they can be themselves and ask whatever question and just be open and enjoy their work. And I think that... sharp elbow instinct with my peers comes from that competitive instinct, honestly. It's no different than if you start a business and again, you're thinking about your competitive advantage. Part of the competitive advantage most companies that succeed have to have is they try to bring down their competition a little bit or they at least figure out exactly what their competition is good at or bad at and they exploit the things that appear to be opportunities for them. And maybe I'll just add one other note, which is the way that manifested for me wasn't maybe the way that it would manifest for someone who's, you know, potentially perceived as like very negative or toxic in an organization. I think I'm just a little bit careful with perception management relative to my peers. You know, I was always careful that if it seemed like somebody was, you know, casting blame or misunderstanding an issue. I could be a little bit sharp in correcting the narrative around what was going on when it came to more like peer level competition. Rohit: When one is competitive in the right sense and a high achiever, the team that is supporting that individual also needs to be at least on par on performance with that person. How did you find during your tenure at, whether it's Zendesk or ClickUp, the support from the team? And I'm sure there were instances where some people were not able to scale as fast as you were scaling and demanding them to scale or demanding them to scale. And at times, people were just able to make it work as well or maybe even better than you are doing. Maybe do you have some anecdotes in terms of how did that pan out? And in that kind of realm, how do you think about picking the right people who are able to support you in your journey as well as the overall organizational journey? that all of you are on together. Alex Small: Yeah, I would say I definitely ran into those cases where people struggled to scale at the rate that I was scaling. And there, yeah, there's a few ways to look at it. I would say the things that I look out for are whether that person has a place in the organization or not. Cause you know, the first thing is, you know, am I trying to hire a whole bunch of me's like, not really actually, you know, like I'm not, I'm not trying to hire a bunch of people that are going to, you know, stay one. one rung behind me on the ladder as I move up. You know, like I'm a senior analyst, I hire an analyst and I expect by the time I'm a VP, they're a senior director. You know, I'm not really even aiming for that. That would be great if I could find some people like that. But if you have an org full of people like me or people like that, you tend to end up with a pretty intense workplace and you end up with like an overly senior workplace, you know, where you don't have some of the folks who are more content to manage some of the line tasks. And so I tried to build a balance. I tried to find those couple of people throughout my career that were going to be my, you know, uh, buoys, my, you know, lifeguards, the ones who are going to be by my side, make sure that things were successful, uh, that I was working on and could also sort of benefit from, you know, being, being by my coattails to some extent, you know, like really, you know, follow me along that career journey and also have a lot of upward mobility. And I could point to exactly who those people are. And I owe them a lot. I think they might say they owe me a lot. And like, we've had a really great, you know, professional relationship. And then there's a lot of people that I've worked with that, you know, maybe were more content where they were, or they were just more effective where they were, versus, you know, having that ability to progress quite as quickly. And in many cases, those people are still great. You know, if you have someone who... you know, wants to answer customer support tickets and enjoys doing that and does it well, but doesn't have the aspiration to become, you know, the VP of customer support or, you know, chief operations officer. As long as they're good at customer support, that's great. And sometimes it's a capability thing. Sometimes it's just a motivation thing. But it's important to have a lot of those folks around as well. As long as you're in a growing organization, you can handle having a few more of the high ambition folks. If you're in a more stable stagnant organization, you're probably going to need to actually err even further towards, you know, those folks who have less ambition, otherwise you end up with more attrition, you know, and a lot of times tenure is more important than ambition as long as the capability is generally there. Um, so that's a little bit about how I think about it and how I think I've, I've managed to thread the needle of having those people that are so strong and kind of like right behind me in their capability, but then also just some of that infrastructure that just holds the whole team up reliable. Rohit: Makes a ton of sense. Let's dig a little bit more into Zendesk and ClickUp. They're both in a very competitive market. Zendesk was a Valley darling and then did quite well in the public markets as well. There, you have spent most of your time while they were public before being taken private. ClickUp seems to continue to kill it. From your vantage point of a finance and strategy professional, how do you dissect the positioning of each of these companies in their respective spaces, if you have specific sort of thoughts on that, maybe we'll start with Zendesk first. Alex Small: Sure. Yeah. Zendesk was always interestingly placed in the market because they were kind of a first mover in many ways, at least a very early mover in the customer support software space. And they use that to good advantage. I mean, they're a huge player in that space, but they ended up navigating into this position of sort of being the mid-market company, where Salesforce is very much the enterprise company. And then there's, you know, frankly, like a thousand companies that are at the lower end of the SMB space, Freshworks being one of the biggest of them, Intercom being another big one, and there's just a lot there. And so we ended up saying at Zendesk, thinking through this with them in many cases, as a leader in their finance and strategy team, that we needed to really consider our place in the market. We had to nail down a niche and try to build from there, but really win somewhere. And what we usually came back to was... Well, SMB is not as big of a TAM as we really need, and there's a million players in that TAM, and it's just not gonna be easy to have a massive market share there, so it can't be SMB. Enterprise is really enticing, but not only do you have Salesforce, but you also have a lot of other platforms out there, even like solutions from like Twilio had something that was kind of competing with us. We use them for voice, but then they started to actually kind of pull some customers over on that front. with some capabilities that they had. And there's just a bunch of other ServiceNow, various other pieces of software that started to compete in various ways on the enterprise side. And we also just didn't really invest, I think, as much as we needed to in enterprise to become one of those key enterprise players on the customer support side. And so we said, while we were considering this whole enterprise thing and like, frankly kind of half doing it. we said, okay, well, our sweet spot is mid-market. And we really did well there. We were like the best player in mid-market, I think, pretty objectively. I mean, we had a huge market share. We were winning a lot of deals, good win rates. And then the story just became one of kind of like a question mark over time at Zendesk of, okay, do we really break into enterprise and how are we gonna beat all of the other folks who are up in enterprise? Or do we go kind of curve ball with our next move and... Think about either like our CRM tool. We had one we called Sell that was from an acquired company that was competing also with Salesforce, on their CRM side. And we could become kind of like an SMB mid market, HubSpot competitor CRM if we wanted to. Or we ended up having this kind of concept of becoming a customer intelligence platform. And that's where the failed moment of acquisition came in. And that was just, again, one of these opportunities to diversify what we were doing, innovate, and try to leap ahead of competitors by going in a different direction. And candidly, I'd say that it just failed. The momentum acquisition itself was rejected by shareholders, and since the company was acquired by private equity, the CEO has left. And so it's like, not that the company itself has overall failed. It's still going. It's still great customer support software. It was kind of like a failing to reach the next level, I would say. You know, they kind of tapped out there in the mid market and they'll probably continue to be kind of a mid market player for a very long time. Is my expectation. Rohit: Got it. What about the click-up side of the house? They are I think intensely competitive horizontal market with tons of people coming in from various different shapes and sizes. Alex Small: Yes. Yeah. Uh, so the ClickUp story is an interesting one. You know, they are a young company still, and they've just done an incredible job of breaking into the productivity software market. That's what attracted me to them. You know, it's this incredibly splintered competitive market, uh, that is, you know, hard to consider an enterprise markets, you know, technically they're enterprise customers, but, you know, do they need this software? They're going to use this software. There's a lot of kind of like existential questions around it. And they've still managed to thrive. They've got some really big customers. They've got tons of customers across SMB and mid market, and they have some pretty clear differentiation in their capabilities versus the other main competitors. The other competitors that we looked at when we were there were mostly Monday.com. That is like the definitely the leading competitor. The most obvious one, Asana was absolutely up there and a very strong competitor. And then we looked at. things like, especially Atlassian's Jira kind of confluence capabilities as a, you might call it a secondary competitor, but still a very like significant competitor around certain capabilities of the platform. And the way we, you know, we're starting to see the market shape up was that ClickUp was able to beat the competition in the low end of the market a lot of the time, because we had great branding and great ease of use. And we also introduced a lot of features before these other companies, and they ended up copying ClickUp. And so ClickUp is just, it's innovative, I feel, as a company in this space. And that was a huge part of what attracted people to it. Where ClickUp struggles is around like buggyness, and refineness of the platform. It is just young, you know, it's not refined yet. And we've prioritized features to some extent over some of the foundations of the platform. I think they're really getting that under control now. You know, like reliability is better. A lot of the bugs are fixed. A lot of capabilities are more well-rounded. Um, but that's been their story of, you know, being innovative, but just not quite, you know, like refined, uh, because, because of their youth. Um, but I would also say even as they're, you know, now focusing on getting their foundation shored up, uh, they're starting to lose a little bit candidly on, on the, uh, innovation side. Uh, you know, it's like, you can't have both. And so you see, uh, monday.com. and Asana, ClickUp, a lot of these other tools, starting to all look the same. Most of the capabilities are starting to become very similar as they all reach some semblance of maturity and they copy each other whenever one of them has a good idea. And so it's becoming a little bit more like a commoditized market, which is part of the reason that I decided to move on. I don't mean to say that ClickUp does not still have a compelling story ahead of it. I think there's enough room in that market for all of them to be very successful. But for any of them to become the next $100 billion company, they're going to need to do something that is not the same as everybody else. They're going to need to become more niche. One of them is going to have to displace Atlassian as the tool that you go to, the company that you go to for developer productivity software, for example, for them to really break into a many tens or $100 billion opportunity. Maybe it's a ServiceNow market, too. Maybe they get into IT CRM. Maybe there's markets like Coupa, procurement, there's a lot of great workflow stuff you can do inside of these software suites. But I think when it's just seen as the project management tool, there's a limited market there actually, and a lot of competitors in the space that are all starting to look pretty similar and have most of the features that you need for that. There's only so many features you can build for project management. So I see that as a potential limiter for them and that's... the next chapter of their story is like, what is their differentiator? Can they continue to? Rohit: That makes a ton of sense. You know, as I think about most software markets aren't necessarily a winner-take-all market from a, you know, market share or revenue perspective, but certainly a large portion of the value inures to the leader, right? Funding is relatively abundantly available for the right kind of... founders and concepts and businesses that are coming up. In that pretext, is 30% EBITDA margin dream of any SaaS company really a dream or a mirage? Is it a secret to achieving that? Having seen so many businesses, do you have a formula that you feel like, hey, this is the right way to get there and sustain? Alex Small: Yeah, it's a good question too. Yeah. So I have a couple of thoughts on this. One is just had a really great conversation with a CFO recently who was talking about his growth and profitability framework. And it's something that I've spoken to multiple CFOs about and kind of had myself in the past, and I think it's really important to think about EBITDA margins in that lens, you know, you need to have this concept of. Yeah, you can get to 30% EBITDA margins if you want to, but you're probably gonna kill growth to do it, in most medium-sized, semi-mature businesses. And so I think it's almost maybe in my mind, more of a fallacy of, oh, is anyone actually gonna get to the 30% EBITDA margin? I think they will, as soon as they are willing to slow down the growth rate. It's just that growth is so worthwhile relative to margin. that most companies, as soon as they get to cashflow breakeven, they say, let's reinvest. Every dollar I put in, I'm getting $2 out or $3 out. So why would I just take the dollar out instead of getting $3 out in a year? SaaS is just such a good business that it leads to a lot of reinvestment. And it's definitely not the universal story, but I think that's a very common story. Zendesk, for instance, was growing. at let's say 30 to 40% for many years while I was there annually. And we had a EBITDA margin, I want to say, well, non-GAAP anyways was positive. If you include the equity compensation, right, that's a whole different story, but a whole other kind of debate to have. But their non-GAAP margin was positive by, I want to say. 5% nominally positive and cash flow margin was materially positive. And so if they wanted to, they probably could have just slowed down growth and they could have gotten to a 30% EBITDA margin and even a GAAP profitability of some level with a significant cash flow margin. But would that really have been the right thing for the business? I think investors would have said, I'm out. You would have gotten a decent valuation on the cash flow. And that's like a nice. business that will last for a while. But as soon as you stop investing in R&D, you stop investing in S&M, you're gonna end up with slower growth and then increasingly slower growth over time as your product falls behind. And so that just is a much less compelling decision for folks to make, especially when they have the pressure of being public. That gives me the reason to bring up one other, like, I don't know, pet peeve, I guess I might say, of mine, which is... the notion of being beholden to investors. And there's no easy solve for this. But it is just so sad to see how many businesses make decisions based on what their investors or what their board members are going to kind of demand from them versus taking the four to five year out view of it. And I think in many cases, going for profitability over growth, in my opinion, and of course, it varies by circumstance a lot. would be something that you're going to get investors pushing for in certain circumstances that might not be the right thing for the business. It's the classic Jeff Bezos quote, I believe. I think a number of famed business leaders have said this type of thing. But I'm baking the quarter three years from now. People congratulate me on the quarter I just had. And I told them, cool, I made that quarter three years ago. So I'm thinking about what three years from now. Those are my thoughts, but also recognize that profitability has to be attained at some point. And so I do wonder what the future holds for a lot of these SaaS businesses and if many of them will eventually start to make that pivot away from growth towards profitability. Rohit: Yeah, because as I think about it, as a technology business, you need to invest in R&D. As soon as you stop investing, you are going to fall behind the up and coming competitor who's looking to snatch up that market share from you with doing something different, something unique. And there is always a new paradigm that is coming in, whether it's mobile, whether it's like this is cloud, mobile, and then now sort of AI. you need to continue to invest. And it seems like, you know, there's always day one, right, for something that you want to put money into. But interesting, interesting conversation. And I think from a capital allocation perspective, it's an interesting problem for finance folks to solve as well. Alex Small: Yeah, I was just going to chime in on your previous comments around R&D investments and mention that I feel it's one of the most interesting challenges for finance folks these days to think about developer productivity and the ROI of investment in development of certain areas of software. Inevitably, it's the question CFO asks, CEO asks and even in some cases, even the heads of products engineering are asking, how do we make sure that our folks are being high ROI, that they're working hard, that they're productive? And then how do we know that we're investing in the right products that are going to get us the ROI that we want? And those are incredibly difficult questions to answer on the finance side. I think you can do some interesting surveying. You can look at the market and you can examine just cases, scenarios of potential user... you know, numbers, adoption numbers, and, you know, the revenue that can be associated with that to try to build scenarios. But it's something that I feel, you know, it needs to be a partnership with a lot of the other organizations in the company. So just sharing an anecdote, I had a great partner at Zendesk that did a lot of market research and was also a product for business operations and strategy and pricing and packaging person, very well rounded individual. And so I was able to use, you know, my finance experience and his product and kind of market knowledge to help create these informed scenarios around what products might look like, adoption might look like, pricing and packaging might look like, and therefore ultimately revenue might look like. Compare that against the potential investment that can be put behind it in terms of people dollars and come out with some sort of theoretical ROI. Were those numbers ever accurate? That's a very good question. The question I know the answer to in many cases, it would take years for all of it to play out. And so we don't really have good actuals against the scenarios we made. But it's something that I feel needs to be further explored in the finance world to try to make those hard decisions. Rohit: Makes a ton of sense. Couple quick questions on SaaS metrics before we move on to our deep dive on the strategy piece of it. So top five metrics that you would use to track a company like Zendesk, which is serving the mid-market to maybe enterprise software. Alex Small: Yep. Uh, sure. Yeah. There's a few SaaS metrics that I'm particularly a fan of. Um, the one that I became just inundated with at ClickUp was a CAC payback. And I do think it is probably the most important metric. Um, of course, I mean, everybody's probably familiar with this metric, but just to quickly talk a little bit about it and then, you know, why I think it's the number one metric, um, it is basically the amount that you're investing in your sales and marketing. How long is it going to take you to pay that back with the revenue that you're getting from that sales and marketing? And there's some very like clear, uh, guidelines around what CAC payback should be. I mean, generally, if you're looking at more than a couple of years out, you just, you don't have a machine that is going to be building on itself. If you have a CAC payback, that is something like 12 months or less. you're going to be able to create a flywheel that is able to compound on itself very, very fast, right? Because you can invest a million dollars in a year and you get back a million dollars that year. And presumably, if you have that good of a CAC payback, you're also going to be getting from that same million dollars, at least, let's say like 800K the following year and then 600K the following year, assuming some kind of turn in contraction on it. And then that's all money that you can invest in further growth, which further compounds. And you can create an exponential growth machine. So a CAC payback is probably the single best descriptor of putting money into the business and the go-to-market engine and being able to compound that and the rate at which that is actually happening for you. And going beyond that, I think there's another piece that's really important, which is customer lifetime value. And maybe I'll cheat and call this three metrics, but. Customer lifetime value, CAC payback, and then the ratio of customer lifetime value to CAC payback are a kind of suite of three metrics that are incredibly valuable in understanding the business. You know, again, folks probably aware of these, but customer lifetime value, just understanding how much your customers that you're bringing in are actually worth over the long run and then comparing that to the CAC. You can get a similar kind of ratio to CAC payback. But I think an even more valuable one because I should say they're both incredibly valuable. Maybe you look at them in parallel. The LTV to CAC number helps you understand for every customer you're bringing in, you know, how basically every dollar that's, you know, coming in as revenue, how much is that going to multiply? You know, every, sorry, every dollar you're spending, how much is that going to multiply? And that's important in tandem with the CAC payback because it's important to make sure not only that you're optimizing for total value to the business, but also speed of value to the business with the former being LTV to CAC and the latter being CAC payback. Um, so, you know, all that to say, if you have a strong LTV to CAC, but a bad CAC payback, then that tells you that you do need to worry about monetizing faster. But at least every dollar that you're investing is going to get you. a large amount of value for the business. And you might see something like that with, let's say like enterprise deals, enterprise SaaS software, or any kind of product that is enterprise related, where you're probably gonna have a very long, very expensive sales cycle. And so it's gonna take a long time to get paid back, but you're actually gonna see low churn rates and high expansion rates and a huge amount of overall return on your investment. And so having that dynamic doesn't necessarily mean you're doing something wrong. enterprise sales can be very lucrative, but it's something to be aware of. It means you're going to have to just believe in that engine continuing to run and, you know, accept some of the pain of that long cash payback upfront. And if you experience that on more of like an SMB sales cycle, then you should probably examine what you're doing wrong because there should be an opportunity to monetize faster in the SMB side. So those are a few of the dynamics that I look for. Outside of those, I'm very partial to rule of 40 metrics. So basically, thinking of that intersection of how much cash flow margin you have relative to your growth. And that comes back to the growth and profitability framework that we were just discussing a moment ago. Those are really the two things to trade off against. It's like, how profitable are you as a business and how fast are you growing as a business? It's very difficult to do both very well. And so oftentimes, even if you're a very effective business and so you're... rule of 40 number cash flow margin plus revenue growth percentage year over year is over 40 or is some very high number, you still then have to think, you know, are we at the right intersection of the two? You know, would we rather be less profitable and then have higher growth rate and then, you know, we can become more profitable later? Or would we prefer to go the other way around? And, you know, if you'll need cash, you know, preserve for downturn in the economy or whatever. You know, kind of what I was mentioning earlier is I think businesses should optimize more towards growth early on. And then if they find that getting to a certain level of growth becomes excessively expensive, it can make sense based on those efficiency measures like, you know, LTB to CAC and CAC payback to start to value profitability a little bit more. That can overall boost your rule of 40 total. you know, allowing you to take some of the diminished returns, very expensive growth dollars that you're putting towards revenue growth and put those back into your cash flow margin. So those are, you know, again, a few more of the key metrics. I'd say the last one that I want to highlight for me is churn. And having been on the customer experience side of the business for a long time, most of the things I just talked about, like churn is baked into them. Right. So. You can kind of consider it covered. Those are some of the biggest, most important metrics of the business. But journey contraction tells you a lot more than just, uh, you've lost some dollars and it feeds into other math, right? Like journey contraction also tells you how you're doing from a competitive perspective, from a customer experience perspective, and, uh, from a, you know, just efficiency of go to market perspective, even if some other metrics appear generally healthy. but you see turning contraction worsening, then you know that you're probably moving in a bad direction as a business. You know, you've fallen behind on something, something's falling apart in your customer experience motion, or something else is happening in the business that is maybe it's pricing and packaging related, that's going to be a big problem down the road. So I think it's an incredibly important metric to monitor in isolation. Could say the same for a lot of other metrics like expansion rates, there's a lot of important metrics, but those are a few that I am most partial to watching very closely and thinking a lot. Rohit: super helpful to unpack that. You're now part of Stripe which is of course a fintech company and have multiple different streams of revenue whether it's interchange or different kind of fees that they charge and so on. Having seen now that different business model so up close, do you have any thoughts between that pure SaaS recurring revenue business model versus kind of a Stripe kind of a model, which is much more dependent on every transaction that their customers or at times the customers' customers are doing. Alex Small: So I personally feel that there's advantages to both business models. It's been actually incredibly interesting being at Stripe and having the opportunity to learn a different business model, learn the dynamics of it. There's a few things that I would highlight. So one, SaaS is in this world of incredibly strong margins. The only reason a SaaS business would have a lack of profitability is because they're very inefficient or they don't have a product that people like, or they're just investing a lot in growth. All of those things can be realities that good companies experience at some point in time. Then maybe they grow out of them, they fix them. Or for example, the heavy investment in growth can just make sense for periods of time when you have the money for it. So I don't want to disparage any companies that have those realities, but basically it is kind of easy to have good margins in SaaS. It is very hard to have good margins in payments. So Stripe is constantly thinking about the BIPs, the basis points of margin that we have on every deal. People might think, wow, like Stripe is making tons of money. Look at that, like three points of margin that they take on every transaction. They must be absolutely rolling in it. But the reality is that we have to pay our partners. So Visa and MasterCard end up taking most of that right off the top. There's only like, you know, sometimes, you know, 60, 70 BIPs that's left even in a full, you know, margin deals, one that doesn't have any discounting. Like, we haven't been negotiated by the customer at all because Visa and MasterCard are, you know, the primary payments processors for transactions that customers are using on most platforms that use Stripe. And we just, you know, out of those three points that we take, we pay Visa and MasterCard, you know, for the customer, for the business. So that's an important thing to be aware of. It's a low margin business. But on the other hand, I would say it also has this amazing TAM and in some ways some really good economies of scale and some huge efficiencies. So let's talk about those individually for a moment. TAM is actually a challenge for SaaS businesses. Maybe at times in my career I've thought of SaaS as being a gold mine and have this super high ceiling. But actually, even at Zendesk, for example, when we looked at the TAM that we really thought we could go after, I mean, let's say it's more like the SAM, like we did some exclusions based on customers were actually likely to be able to win, it was something like, I want to say like 10 billion, 10 to 20 billion, which yeah, it's a lot of money. But actually, if you're trying to be a trillion dollar business or even a hundred billion dollar business, being in a 10 billion dollar TAM is not good. You've got to really expand that TAM. to be able to grow beyond, let's say, 50 billion, because you're not gonna get the whole TAM. There's a ton of other competitors in the space. So you're not gonna get 10 billion. And on top of that, it's just gonna get harder and harder to grow when you're starting to reach the upper ceiling of the TAM. So your growth rate's gonna be completely limited. You're not gonna have revenue that can translate into high margin growth. And that's going to end up damaging your valuation. So you're not gonna reach those lofty heights. In payments, The thing about the TAM, it is, let's say, a couple points on all of the revenue in the entire world that's being done digitally. And so we're talking about, I don't know how many trillions of dollars as a TAM for payments. It's huge. And actually, 1% of the GDP of the world is being done through Stripe. And so that's a pretty good bite taken out of the TAM of the world already. But there's still a lot more to go for companies like Stripe to look at. And there's, of course, like a lot of digitalization that's still possible for a lot of these businesses out there. And so that TAM is actually still growing. And GDPs are growing. So I would say, you know, there's some key differences on the TAM side, some key differences on the margin side. If we look at as well, just like the business models themselves, there's a big difference on the complexity front. And it was actually really interesting going from being a finance person at SaaS companies to being a finance person and one of the most complicated, uh, fintech platforms in the world. Uh, because. I mean, really, if you think about it in a SaaS business where, especially there's like only one product, let's say, which, you know, Zendesk had a couple of minor products on top of core customer service and had some channels within customer support, different plans, you know, there's a little bit of complexity there. ClickUp had one product with a few plans, and it was a multifaceted product, but it's still basically one product. Go to Stripe, they have, I don't actually know how many dozens, literally dozens of products, and each of those products needs to be specialized for every single country and every single market segment, and to some degree, each type of customer within each of those market segments. So if you think of a market segment as like a revenue band. There's going to be differences between how you need to manage those products for an enterprise and the types of products you build for enterprises. There's going to be differences in, for example, again, on the industry point, if it's a platform that is repackaging your services versus if it's a e-commerce company, you're going to have very significant differences in how you're building that product. And then let's look at all the countries in the world. So do you think the regulations and the financial infrastructure and the bank processes of Uganda look anything like those that are in the United States. All the rules around all of that, they don't. It's all very different, actually. If you think about trying to create a payments provider that can actually legally interface with all of the different banking and financial infrastructure platforms around the world, and do that reliably without making any mistakes, that is just the most incredible challenge to imagine actually building as a product. So Stripe has its own just like world of teams, things like policy, you know, partnerships are incredibly important at Stripe. Reliability and security are incredibly important to Stripe. If Stripe ever got hacked, you know, that would be the end of Stripe basically, you know, the reputation of the company would be shot, people would never trust it again. So it's just, it's dealing with challenges that you just don't even imagine in a SaaS business. So it's actually incredible to me that companies like Stripe have been a successful. as they have with all of the challenges that they're facing. And it really, it comes down to, you know, there is also a really compelling financial prospect there. Like the business model does have a lot of advantages with that massive TAM, with the ability to just collect bips off of deals without having to be a part of every one of those deals. They're not really doing a lot of customer service, you know, for each of those deals. It's more customer experience for the customers who are then having to handle their... their customers' interactions with payments. And so they handle that piece. So there's inherent advantages too, but overall all that to say, it's a very competitive space because there's a lot of opportunity in it, but Stripe has done a remarkably good job and it's a very complex space, remarkably complex. Rohit: Yeah, I bet. Thanks for, I think, that great explanation. I would imagine a lot of eyes are on now kind of the IPO that everyone is hoping for. So yeah, fingers crossed. Let's move on to maybe a master class on strategy. The general, I would say, uninformed perception is this is perhaps the best job ever. You talk to people internally, you talk to people externally, and then you turn around and pontificate what should be done without any burden of execution. So maybe unpack that for us in the context of what is strategy to you. Alex Small: Yeah, yeah, happy to do that. And yeah, it's so funny. Strategy is this word that gets thrown around and means so many things in every company, even within the same company. There's no real consistency that I've seen around it. I'll tell you a few of the things I've seen it mean, and maybe have an opinion on what I think it should mean and how people should think about it. For one, everybody these days likes to put strategy in their title just because they think it's glamorous and it's like the senior thing to do is to be strategic, right? And that's something that I think management is perpetuating, whether they mean to or not. I know throughout my whole career, I was told, you know, like, need to be more strategic. You know, that's how you're going to get to, you know, X, Y or Z level. And in a way, Rohit: Our whole podcast is Strategy of Finance, right? Alex Small: Yeah, yeah, yeah. So you're doing the same thing, right? Yes. And strategy is a senior thing and an elevated thing, right? And I think as you become more of a business leader, you do have to be better at strategy. So there's realities to that. I do think, though, that putting strategy in your title just for the sake of having it in there is a little bit dilutive to what strategy should be, and it also removes in a way the facts or the implication that all of the other teams that don't have strategy in their name shouldn't be strategic. And so, you know, another conversation I had with the CFO recently, which I thought it was a really great conversation, he had mentioned that, you know, for strategic finance, for example, or finance and strategy, as you know, FP&A is often being rebranded these days. It is a little bit of a problem that we're moving to all of these like strategy names because realistically, every business unit, every team should be strategic. FP&A should be very strategic. HR should be strategic. You know, legal should be strategic. You have to think about whether you're doing things that are for the benefit of the business versus just like operationally sound and think about whether there's ways to innovate on how you're operating. And to me, those are... the ways that strategy should find its way into most teams. I would argue that finance has an opportunity to be slightly more strategic than some teams by looking at the finances of the business. They can help the company make better strategy decisions, overarching company strategy decisions. And so that's to me what real strategy is. But maybe just taking a step back from that debate around words and talking a little bit about. what strategy has meant to me and the career path that I've been on. Having been in roles with strategy in the title for 90% of my career, I found that typically the distinction when it's done right is that these strategic roles are roles in which you are actually connecting operations or finance to strategy versus getting to be the hands off. person who speaks about how things should be and doesn't actually end up doing anything about it. I have seen a few instances of folks being true strategy folks. It's usually like the corporate strategy team, you know, someone who does not have operations also, or finance also in their title, who does the real hands off strategy stuff. There is, you know, I'll say a team at Stripe that is corporate strategy that talks just about like, the strategy of the business and thinking about how other businesses are conducting their strategies and helping to kind of agitate the thought process around how the business should operate and what their strategy should be. So yeah, that's a little bit about it. I mean, I think it's the last thing I would say is for all of those folks out there who might be listening to this, watching this and thinking about their relationship with strategy. I think what's important is to be, an influencer of strategy, not to have it in your title necessarily. You can do it from any function, you know, by being a leader in your space, helping to make decisions around how to operate and helping to support the company strategy and actually make the business more successful. Uh, you can appear and be more strategic and influential from a strategy perspective. And ultimately drive value to the business. I don't think having it in your title is actually the key thing, nor is it usually a good excuse to not be hands on with actually driving the business. Rohit: How do you segregate good strategy versus bad strategy? You know, as we discussed, it's such an amorphous, maybe a very big ticket umbrella word. How do you make it more tangible? Alex Small: Yeah, that's a good question too. I would say strategy is good when it accomplishes something for the business and it's bad when it doesn't, right? And that's like the most fundamental thing. To know what's a good strategy, I mean, first of all, it needs to be a well-formed strategy. And that's, you know, a little bit separate from it being the right strategy. But I would say a well-formed strategy is one that is comprehensive and actionable and communicable. You know, so there's a lot of strategies out there or things like, you know, go big on enterprise, you know, it's like a very, very common strategy. I've been in a lot of companies where that was the strategy or as part of the strategy and that's fine for that to be the headline, but there needs to be a lot underneath that around what that actually means. And so this is where that connectivity of strategy to operations comes in. And there's somewhat. Seamless, right? They need they need to be interconnected because a strategy like go big on enterprise that doesn't articulate like what product, what features of the product, who's building it, what the time frame is, how we're measuring it, with none of that in place you're not actually able to go action on that or too many people are gonna action on it You know or no one's gonna action on it even though they could like there There's just it you're not going to see the results you want And I see that actually coming back to one of our earlier topics as one of the most important capabilities of a FP&A or strategic finance team. It's to be at that intersection of the strategy that, you know, the CEO might have in mind, which is, hey, we got to go after enterprise and like, you know, guys, can you all go and, you know, work on getting us to be successful in the enterprise and connecting that to the financial realities of. Why are we doing that? Let's double check that this makes sense. Okay, like makes sense. Then what does it mean financially? Let's plan for that. And then all of the operations that are gonna ladder up to making that effective. And finally, the communication around all of those operations. The communication piece of it and some of the operational pieces of it can fall a little bit outside of the finance spectrum, but connecting those dots, seeing where there's problems, seeing where there's misses, and then pulling in the right teams. to make sure that the right things get done at the right times can be an incredibly powerful motion and is where the like strategy portion of a strategic finance team's name really comes into play. Rohit: Makes sense. As we discussed, there are so many different types of strategies, right? It could be business strategy, product strategy, go-to-market strategy, finance strategy, people strategy. Like every single function could have their own strategies, if you will. How should one think about the role of the strategy leader? What all should it cover, not cover? Are there kind of certain... best practices that you have seen that kind of makes sense to put under the purview of the strategy leader. Alex Small: Yeah, I've seen it done a few different ways. Uh, we had, for example, a chief strategy officer at ClickUp and his role ended up being very focused on company strategy and then also equally focused on, uh, the partnerships organization. This is before I took over that team. And I would say that candidly, I don't know that was the right setup. I think it's important that strategy leaders have a purview over parts of the business that are most strategic. And so partnerships is one of those, absolutely. And it would make sense to have that there. He also had corporate development, and so mergers and acquisitions type responsibilities, which are very strategic. But the challenge that we saw there is that he was not a product strategy leader. And I think it's important for folks in finance and in any function to recognize that I mean, there's a few pillars of strategy. Like one is like the corporate strategy of, you know, things like, uh, you know, mergers and acquisitions, and then there's the go-to-market strategy, which encompasses partnerships to some extent. Uh, really partnerships can be in all parts of strategy. Um, and then, you know, a number of other elements of go-to-market strategy, like what is our marketing strategy? Who are we marketing to? What is our ideal customer profile? What are the channels we're going to go after the sales strategy of, you know, are we. hiring senior enterprise reps, are we going to do more of a self-service motion? There's some key elements there. But product strategy is the piece that really makes or breaks the company over the long term. And I think as a finance person, I find it's easy to get enamored with the go-to-market side because it feels like a math problem and it's very logical and actionable. You put in reps that cost X, Y, and Z amounts and you get out. X, Y, and Z revenue, and you can have a capacity model that tells you how many reps you need for how many bookings. And it just feels like this cool machine, and it's considered glamorous as well as a part of the business to work on. Whereas a product for a finance person is often not quite as glamorous because you're more just looking at head counts and maybe categorizing people. You do some reporting. It's a different type of work a lot of the time, but that's not how actual strategy in the business should work. you know, product strategy should lead everything else from a business strategy perspective. And I would say the best finance professionals can find themselves in the product strategy sphere. If they get into some of those same things that I mentioned earlier, you know, I had delved into with my partner at Zendesk around, you know, what are those products that we're building? What are the pricing and packaging scenarios we can have around those? the adoption scenarios, and then, you know, even talking a little bit about like the features and understanding the market well enough to understand the TAM and the upsell opportunities, the cross-sell opportunities that you're creating, that becomes highly strategic and revenue oriented instead of just headcount and cost oriented on the product side. So I'm kind of mashing together, you know, two realms of strategy, one being the like centralized chief strategy officer, head of corporate strategy type role. and the other being more on that financial strategy side. But ultimately, I think one of the most important things for both of them is to think more about product sales and product building opportunities and the resourcing and staffing around products to make that engine effective. And the go-to-market engine needs a lot of attention too. Finance is a huge part of that. but it ultimately comes after. Without the right products, there's no reason to hire salespeople. You're not gonna get the demand that you need to actually sell into. Rohit: It makes a ton of sense. It seems like different people who are ultimately impacting strategy are sitting in various different parts of the business overall. Is there a thesis around having a separate strategy team altogether within a company? What are your thoughts around that? Does it... even make sense to have such kind of a structure? Or is it just something more that maybe there is one or two individuals who are in that team and then the rest of the folks have a dotted line into them? Alex Small: Yeah, that's a good question. There's an interesting reality in business that the more skills you try to cram into one individual, the more expensive that individual is going to be, the more rare they're going to be or the worse that they're going to be at all of those things. And so I think that it's a constant challenge, a trade-off challenge. because ideally you have a business full of high achievers who can do everything and work together super well, right? But that's just not the reality. And so then some people, I think, pivot towards this idea of, okay, let's have specialists for every one little thing and then they'll be amazing. Everyone's gonna be amazing at something and then we'll just find ways to get them all to work well together and coordinate well. That actually doesn't work that well either. You know, like the right answer is somewhere in between. You need to have some people who kind of span everything and then find ways to centralize the right things and decentralize and specialize the right things. I think that strategy is probably one of those things that needs to be a little bit spread throughout the company because to be an incredible product strategist or an incredible go-to-market strategist, you have to be just steeped in that line of work. You know, you really need to understand the realities on the ground. the operational realities, it's going to help to have been a sales rep or to have known and worked with a lot of sales reps to be a go-to-market strategist, just like really know their pain points, their capabilities, their opportunities, and to know the selling of the product and what's possible and know the product well. And that's where you start to see a little bit of the synergy, I guess I would say, in being more of a diversified strategist and like, okay, well, what if you're a really good product strategist? and you're a really good go-to-market strategist, then you're going to have this ability to actually say, I know our products so well, and I know our sales team so well, or like our opportunities on both sides, that I can now interweave the two and really advise optimally across the company. But what I would say is that then becomes such a rare and hard defined skillset that usually that person that can do both of those things is like the president or CEO or someone extremely senior in the organization if they're going to do both of those things very well. And so yeah, technically strategy is centralized. It all rolls up to the CEO. And so I think you should have embedded strategic teams and have a touch point in the senior levels of the company, whether that is a chief strategy officer, whether it's a CEO, CFO, there's a few folks that sometimes have. accumulated a lot of knowledge in multiple parts of the business and have them be sort of the consolidator, the one who synthesizes all of that strategic thought process across the business and helps to make sure that something coherent comes out the other side as the actual business strategy, consolidated business strategy. I guess I'll share one thing that might be interesting for folks, which is how Stripe handles this, actually. So we just got through the planning process for Stripe. And, uh, for, for this year, for 2024, we just lock the plan. And there was one person who held the pen, so to speak of the strategy. She's a very senior business leader. She's been with Stripe for like nine years. She's brilliant and absolutely amazing. And, um, it is really, you know, on that product and engineering side, actually. But she's well connected, uh, experienced and has the relationships. to the extent that she needs to be able to understand everything across the business. So she's able to hear what the senior operations leader says, hear what the CRO and the CMO are saying, and also knows front and back the product and engineering side of the house. And so she is just the writer. She's still not the decider, but she's like a synthesizer across the entire business and help to pull the great minds that were specialized in strategy across each of those business areas together where needed to say, I think what you're saying could benefit this person to hear, or I think what you're saying might be different than what this person is saying, you should talk to them. And helped pull together a set of OKRs for the business and a strategy write up. It was literally a long form narrative of strategy across all the different business areas that just articulates what everybody is doing in kind of a cohesive way. A lot of companies are going to lack the like people and infrastructure to do it that way. Stripe has a lot of, again, really brilliant people. It's a very established company now. But to the extent that you can pursue a process like that, I think it was incredibly valuable to have the synthesizer, have the person to pull stuff together. Again, it's going to be one of your most senior people at the top of the company and then have those functional teams that are brilliant in their own areas to help pull things together on that side. Rohit: That's amazing. I wonder what are the OKRs for this person who is the synthesizer, who is the, you know, who holds the pen on the strategy side because arguably she's influencing a lot. But again, she may not be the throat to choke for anything that may or may not have happened. Alex Small: Yep. Yeah. That was the nature of the arrangements, uh, in the way that she handled this in that she knows a lot and is well connected to everything, but she's not actually the owner of any of these things. Almost. But you know, in this particular case, she actually did own a business area also. And so she actually left the process with her own set of OKRs that were for like her business area. Uh, but she didn't own anything else, even though she was partnering with all of these other executives and wrote everything kind of with them and helped synthesize and make sure it all was the right set of things to document. Ultimately, she doesn't have accountability around any of it except her own piece of the world. And I think that's the way you have to do it. I think the role of that person at that level is to help build the right set of interconnected relationships and I guess dependencies and understanding of dependencies that allows all of those people to then come out of the process and feel like even though someone else synthesized and wrote everything kind of with them, for them, you know, alongside them, they're still the owners, you know, and that was really, you know, part of the art of being that synthesizer and that person, you know, at the intersection of all things that she didn't make everybody feel like, you know, even though she called some shots on like, hey, you're this OKR, it's not going to work. You know, it's too complicated or it overlaps with that person's or there's just too many, so you gotta get rid of it or whatever. Everybody still came out of the process saying, like, that's fine, like, what's there is still mine. Like, nothing happened in this process that made me feel like I lost control over this being my set of metrics. So everything kind of has to be discussed and justified along the way. It's an expensive process, getting to that level of alignment. A lot of conversation, relationship building that's required to get there. But to the extent it's possible, I think it's the right way to enter the year with the right aligned set of goals and discussions across the business. Rohit: Makes sense. One of the questions that I wanted to ask is, who should strategy folks report to, whether it's CEO, CFO, COO, CPO? But it sounds like in one of the prior responses, you kind of mentioned that whoever has the broadest purview is the best person to have that strategy team, right? Is that the best way to summarize it? Alex Small: Yeah, I would say that is one of the key elements, one of the key criteria. I've seen a few things work though. So it's interesting. And I think it actually depends maybe a little bit less on like purview per se. And it's almost like, whoever has the broadest and deepest strategic experience is probably the right person. And so I've seen that be different people at different companies. At Zendesk, we had, for example, for a long time, a CFO, Elena Gomez, who was just incredibly good at understanding how each of the different business units should be operated, both strategy and operations, and of course, financials of all of the different parts of the company. And so she was just a force of nature within the company. Any team that she worked with would look to her almost for guidance and respected her opinion on their own areas. You know, she was kind of like the pinnacle of a finance business partner. And, uh, she had come to that from being a career strategic finance person. Um, so she was a senior strategic finance person at Schwab, I believe it was, and then Salesforce, and then it's NSU and CFO. And so, um, I think that that's like a perfect example of the kind of person that has done the rounds, understood all the different parts of the business and can connect the dots of the different types of strategy across the business to create something really strong and cohesive. If you look at ClickUp, I think it was a little bit less clear who that person was, but we ended up having someone who was our chief business officer, who was ultimately the most logical person. He was very strategy oriented and he had been a big part of hiring up all the different parts of the company. He was one of the co-founders. So he was the right kind of well-connected tenured person to synthesize all of that. Tenure is important too. Because of course, like... You can be great at strategy of all different varieties, but if you don't have all the relationships and you don't have all the context of the company you're at, then that's going to be problematic for this type of work. And then again, with the Stripe example, it's someone who is very senior. You might put her in the top 40 most senior people in the company, but she's also not the CFO, President, CEO. She's just a extremely tenured, extremely smart, well-rounded individual. who had a lot of great relationships that she was able to use to help synthesize this. So yeah, it depends on a few factors. Rohit: Very interesting perspective. How does data and technology broadly shaping the world of strategy? Alex Small: Yeah. Um, I think it's incredibly important to leverage data and technology wherever you can. Right. I mean, I think everybody kind of knows that these days, you know, we should try to try to, um, you know, leverage it where we can, I think where it's been influential in my experience and, you know, potentially unorthodox, uh, ways or in lesser known ways is in really giving you like competitive research, you know, because something that like just to name a dynamic that's out there. A lot of senior executives these days will kind of use hearsay of like, you know, I talked to this executive at this company and he's doing this and maybe we should do that. And, you know, I heard that this metric is this, that company. And so, you know, we're behind and we've got to improve that metric. And I think there's a lot of value to that. But I also think it can be actually damaging if it's used the wrong way. using technology, the right kind of benchmarking tools, using the right sort of platforms for pulling together lots of different data points and being able to compare them, even if that's just like a project management tool, basically being able to use whatever means you have to actually amass a lot of data and compare all of that data instead of just leaning too hard on one non statistically significant data point that might be influencing your thought process. Otherwise you'll end up, you know, I've had this example at ClickUp, won't name, you know, exactly the people in the dynamics, but there were cases where folks were recommending things that like, you know, ServiceNow were doing, for example, and I was, you know, just like, you know, ClickUp is not ServiceNow, you know, like we could not be much different from ServiceNow. They're like 100% enterprise, you know, over $100 billion company with an incredibly sophisticated piece of software on like a different pricing model. Like it just is not, you know, comparative at all to our situation. And so if you're going to try to make strategic decisions for the business by just copying them in a vacuum, you're probably going to make the wrong ones, you know? So using data and technology to get the right information, to understand the characteristics of different businesses. look at the results of those different businesses, look at the inputs in those different businesses, and then bring all that information together to influence what we should do. I'll add one other thing to that, which is kind of going on a tangent, but this idea of like first principles, I think is really important. Something that has been popularized by folks like Elon Musk, you know, the idea that... you can copy what other people are doing. You can use processes and technology that's already there. And like in some cases, sure, you shouldn't reinvent the wheel, but you also can accomplish something extraordinary and can only really accomplish something extraordinary if you do try to reinvent the wheel or at least like re-examine the wheel, right? You're not gonna have a better wheel than someone else by much if you start with their wheel and then you tweak it. You know, you have to actually... consider exactly how you want to move or whatever you're trying to accomplish with a wheel. And then think of what the best thing is going to be. And of course, the Elon Musk example is, you know, with cars and its batteries and things like that for the cars that he ended up making. People said, oh, you can only get a car, whatever, 50 miles on a charge. And he created a battery that takes cars hundreds of miles on a charge and delivers a lot of power much faster and makes his cars much faster. And people just didn't think that could be done. They assumed people had innovated the hell out of batteries. There was not going to be any more innovation that was going to be done for car batteries that was going to significantly move the needle and change the paradigm. So all of that again as a tangent just to say, you know, copying other businesses, doing benchmarking and using that to make decisions, one can be harmful if you don't use the right data and technology to make those decisions in a good way. But also, even if you're gonna collect that information, regardless of whether you collect that information, you should also take a step back and consider the principles of the decision that you're trying to make strategically. What are we actually trying to accomplish? How do we wanna accomplish it? What needs to be true once we've made the strategic decision and we see the outcome of the strategic decision? And then how does that influence the decision that we're going to make? Rohit: Makes a ton of sense. Last question in this master class on strategy. As one is trying to build a team around, or build a strategy team, what kind of capabilities should one look to bring in? And would you always bring in someone from a functional team, or rather, hire from outside? Alex Small: Yep. Yeah. Very good question. I have always been a big fan of internal mobility. I've personally benefited a lot from internal mobility. So I think it's incredibly important that businesses prioritize internal mobility whenever they can. The reasons aren't just, you know, because I've benefited from it, but because like the same benefits that I've derived from it are what have made me more effective in contributing to the companies that I've worked for. It helps increase tenure. If you have internal mobility, it's much more likely that you're going to be able to, both learn more and do more and do better, but also feel like you have a career at that company that's worth continuing to maintain. Why leave to another business to take on a new role, to do a new thing when you can just do it internally, and continue your career in the same company without having to remake all your relationships and learn completely new context, you can kind of learn iteratively versus, you know, completely changing everything all at once. So a big fan of internal mobility generally. I think you have to consider still, obviously, you can't just always hire internally. You have to make that same call I was talking about earlier around, could we hire someone better externally versus this person who is internal for this position and With strategy, it can come down to a lot of different factors. You know, it's a little bit different than doing, you know, budget versus actual reporting, right? If you're trying to do budget versus actual reporting, it's pretty cut and dried. Like, is someone on the team good enough for that? Should we promote them into the role, let them transfer into the role, and give them that growth opportunity? Or are we just going to be way better off hiring someone else externally? If it's strategy. It isn't just about being good or bad at strategy. You know, it can be about bringing new perspectives. Sometimes for strategy is really valuable to bring in someone who's had a diverse set of experiences across different business models, different regions, segments, you know, whatever it might be that's sort of relevant to the space you're in. Or someone who's just seen great, you know, like maybe they're not even the most... provocative, you know, like the thought provoking, brilliant, imagineer of new things, but maybe they've worked in strategy at a company that does things incredibly well. And you just really wanna do a lot of things more like that company. And we had that experience at Zendesk in multiple business areas with Salesforce folks. Zendesk was a little bit of like a Salesforce shop, which is ironic because they were like our main competitor. But... we ended up pulling over tons of folks, including Elena, including a lot of her team and folks she brought over. And we really just felt that Salesforce had nailed it with the go-to-market motion and that their products, of course, were like innovative and well-loved. And so we copied a lot and we pulled over a lot of folks that allowed us to copy those things in an effective way. I think maybe that you can make an argument that we didn't always pursue the first principles mindset as much as we should have actually. And we, you know, perhaps at times without thinking through it very rigorously just copied Salesforce. But for Zendesk that often worked pretty well because our products were so similar. We're literally selling the same things that it was hard to copy something and have it not be a good idea when Salesforce had obviously thought through so many things so thoroughly. So that's the main, you know, kind of set of trade-offs I would consider. Rohit: Makes sense. Besides your day job, as you said in your spare time, you are also an investor. You run your own hedge fund as well as now an entrepreneur with Catalyst, a BPO company. How do you manage all of this? Alex Small: Yeah, it's hard. It's a lot. So I mentioned earlier that part of my career magic has definitely been being an extremely busy person, a very hard worker, and that has only continued to accelerate, actually, you know, throughout the past few years of my career. I would say that I'm still applying a similar amount of work to my quote unquote day job. What I'm doing with Stripe, I'm probably putting in 60, 70 hours a week into Stripe. And I've really just made this decision to prioritize these other businesses in a lot of my free time. I think of them as my hobbies. And so I think that helps me a little bit from feeling like I'm just a workaholic, I work all the time. When I'm driven to do something and it's something I'm passionate about and I enjoy, I can do it even if other people would call it work. I can do it for many hours. I'm great at focusing, focus for 16 hours a day working through things. That's what a lot of my days end up looking like. It's put nine hours, whatever, into Stripe a little bit on the weekends too. and then spend the rest of the day focused on my other businesses. I'll just say a little bit more about those other businesses for context. So one of them is Hedge Fund, as you mentioned, and that I have automated for the most part, I'm the only employee, but I've created an algorithm that runs on a platform and I do check it daily and I make updates to it weekly, but it is not a massive time sync. I say the most time I spent on it is actually mostly regulatory. It's quite difficult to stay up to date with all of the legal requirements of running a hedge fund and bringing on subscribers to a hedge fund, everything else related to all the subscribers. Then the other business is, as you mentioned, a BPO. That's been an incredibly interesting business to be a part of. I'm working with partners on that one. One of the reasons this is sustainable is that I'm not actively running everything in that company, unlike the hedge funds and unlike my role at Stripe. I'm working with a number of brilliant people that I had worked with at ClickUp and at Zendesk actually. If there's one thing that I would want to leave this group with, who'd be watching this, is to build great relationships. It's incredibly important and everyone I think will tell you this. You probably hear this all the time. I underappreciated this throughout my career, especially early on, I didn't realize how much all of those professional relationships that you build are your capital. Those are the basis for your future success, whether it's in the company you're at or whether it's in your future entrepreneurial pursuits. And now what I'm finding with this BPO is that all those great people that I built great relationships with. throughout my career, they're now my customers and they're my employees. And so it's like the entire ecosystem of my business, like front to back is basically founded upon the relationships that I've built in my career in finance. And I can't imagine how I would have been successful in launching this business without the help of all these partners to do so much of it, to be partners, both equity partners and financially compensated partners. And of course on the customer side, you know building that trust with all of those people many of whom I consider You know not just you know past co-workers that I built trust with but also friends they're you know much more willing to take a bet on a BPO and on you know me because they've worked with me in the past and they've seen what I'm capable of So I guess I'd say a few things there in terms of how I deal with it one. I work a lot and I do that because I actually, I kind of enjoy, I enjoy those businesses. And two, it's the relationships I've built that have made it possible to be successful in really all of these things. Even at Stripe, you know, the reason I'm at Stripe is because of relationships that I built with past business partners, caused Jeff Titterton to want to bring me over. Rohit: Makes a ton of sense relationships do have a lot of power How do you think about this quote "Starve your distractions and feed your focus." Alex Small: Yeah, that's a good one. I would say. I believe that is something you have to live by to be successful. Um, I find that a lot of people ask me like, how do you focus so much? How do you work so much? And, um, I have to be honest, like, I don't have a great answer. I think I just am good at focusing. Um, I think I like inherently like find it easier to focus than a lot of people. Um, but. I think there is some wisdom that I can give in that I have learned to like literally block out distractions. You have to cut the, you talked before this call, like close your browser tabs, don't get distracted, silence your phone. I do all of those things normally. Like, if someone gives me that checklist of like, here's how to go, be focused on this particular thing. my answer is always going to be, yeah, those are things I just do all the time. You know, like I have my phone on silence. I actually don't have, oftentimes I have my phone on focus mode. And sometimes that pisses people off because they're like, I tried to call you and I can't get through. But the reality is, you know, look, I like, I've got to get a lot of stuff done every day. And if I'm checking every text message, every Slack message, the context switching that is necessary every time you receive a message and you switch off of the thing you're doing. I mean, there's seconds lost. I mean, even if you're like, no matter how sharp you are, no matter how on top of all these things that are happening on either end you are, when you context switch over to a text message or a Slack message or back to the thing that you're working on, you're losing seconds, at least seconds. And if every, you know, 15 seconds, you're getting some communication, which I think, you know, might be the case for me at times, you're basically getting, you know, half as much done as you otherwise would be if you just allowed yourself to focus. Or in some cases, I mean, you get nothing done. for the course of like 30, 45, 60 minutes. So you got to figure out what to, maybe like the other piece of wisdom I would add is you got to kind of figure out like what to classify as distractions and starve those because some people might say, you know, oh, the like Slack message from my coworker, that's not a distraction, that's important. Or the text message from, you know, your mom or whatever, like that's not a distraction, that's important. And those things might be true for you. And you got to really just examine that though, because if you want to burn through 12 hours of like quality work, getting a ton of stuff done for your business or for your career, whatever it is that you're focused on, you've got to cut out other things, you know, like you can't spend half the day reading the news or answering Slack messages or text messages. If you want that half of the day to be full of, you know, creating great presentations, innovating. thinking about strategy and influencing business partners, building financial models, any of these things that really require thought and focus. I think there's a lot of different ways to look at it, but that's probably a couple of the secrets to my success. Rohit: Multitasking is a bane, not a boon. Makes sense. How do you define success? What are you running towards? Alex Small: Yeah, that's really interesting. I have thought about this for myself. And I think there's a little bit of a psychological, philosophical question to consider there. And it probably differs for every person. For me, I've realized that the journey is often more important than the end result, as I think many people will say. I often find myself second guessing, you know, how much I'm actually going to care about the end result of, you know, financial success and business success, which I'll talk more about in a minute, as kind of what I'm aiming for. Once I get there, I often think about some quote or some sentiment that's been shared in the past of, you know, when you're 80 years old and you're, you know, retired and, you know, deathbed or whatever situation and you're thinking back on your life. Are you going to value the fact that you spent 16 hours a day building businesses and made a bunch of money out of it or change the world from it? Or are you going to prefer to have spent that time and feel it was more valuable if it was playing tennis with friends or spending time with your family or whatever other thing? So I'll just say all that to note that I'm not sure I have the right answer here, but the- success that I'm driving towards right now is much more on the working 16 hours a day to build financial and business success side. And the way that I justify that to myself is I want to build businesses that can sustain themselves and ultimately that means at some point in my career transitioning out of my corporate career with companies like Stripe, definitely years out but at some point. and focusing entirely on my own businesses and ultimately getting them to the point that they can live on without me. I would want to create something that is bigger than myself, and not just bigger than myself in the sense that literally I can stop being the CEO or manager of those businesses, but also bigger than myself in the sense that it's accomplished something to change the world that is greater than whatever I could have done for myself. I would love for those businesses to create wealth forever. for others, create prosperity in various ways for others, job opportunities for others, and potentially even change culture, be a part of pop culture, you know, like have some meaningful influence on the world. And then to, you know, from all of that, get the financial success and financial wealth that allows me to impact the lives of my loved ones, family, friends, you know, things like that. So I think there's a number of different goals and I tell myself that once I'm successful enough, I would eventually stop working as much and spend more time enjoying being successful and having wealth. I'm not sure that that's the reality that will happen, but we'll see. Rohit: What is your approach to leadership? Alex Small: Leadership to me is one of the most enjoyable things that I get to do. I actually, I love being able to build that type of relationship with people and do it in a way that I think is different than most leaders actually. There's an interesting quote that I've always thought about which is, would you rather be loved or feared? And then there's a interesting kind of response to that quote, which is, I want people to be afraid of how much they love me. I can't remember who said that. But some famous, I think, CEO or CFO said that. And I think I veered more towards that side, where I want to build the types of relationships with my team, where it's not just that they love me, but they actually are sort of like, there's a fear of kind of like, not having, I guess, that love. like, you know, because it's such a positive thing, you know, that it actually is meaningful, right? And there should be like some semblance of a feeling of potential of risk to that. And like, that sounds manipulative. I'm like, I don't like, you know, think of it that manipulatively like every day, but like, I think there's a, just like a beauty to building the quality of relationships with people to where like they value that relationship with you and they want you to feel like, you know, you can count on them, right? And that I can find others who would also build that kind of relationship with me and build that type of relationship with them. Build just that level of trust in the ability to have a strong culture and to have relationships where people can count on each other. And all of that comes from love, ultimately, or a form of friendship or also like... collegiality that can come from some of the things I mentioned earlier, like psychological safety and treating people with respect, making sure that they feel like they can voice everything that they want to voice, ask the questions that they want to ask. So I definitely don't fear towards the fear side personally. I just am not the type of person who likes to be... intimidating to folks or create negative relationships. I think I'm too empathetic for that. And so a lot of this stuff is just personal to me. I don't think there's a right or wrong answer necessarily. There's like a spectrum of capable leadership attributes. If anything, if I look out at the world at the most successful business leaders, I think I'm in the minority. That can be a good or a bad thing. I think if you look at Warren Buffett, maybe he's a little bit more on the love side. If you look at folks like Elon Musk, he's probably much more on the fear side. And so maybe either way can work. But I would say that most senior executives who have been extremely successful do use an element of fear. I would just rather that be for the people who work with me. a fear that the great relationships and the great things that we're building together could be at risk if we don't all hold our accountability to each other, to help each other out and be trustworthy and reliable for each other. Rohit: The last question before we move into the quickfire lightning round. Would you change anything in your career? Alex Small: Yeah. Would I change anything in my career? I don't really believe in regrets for the most part, because I feel that everything that you do helps create your future self and your future opportunities. And it's so hard to unpack what things would have been like if you hadn't done the things that you did. And I think that applies to everything, not just careers. So I try not to second guess too much. I think the short answer is just no. There's certainly things that I sort of wish, maybe that I had started my career earlier. I was like, maybe I should have done internships during school. Maybe I should have considered getting more into technology in some of my earlier jobs that I had during school. But I think ultimately the way things played out have been pretty fortuitous in many ways. Like I've built relationships that feel like the right ones to have today. And I've gotten the experience that's allowed me to, you know, be building things today that I'm very excited about. And I've worked with some, some great companies and I have been successful at them. So it's hard to have regrets about any of that. Rohit: Awesome. Well, that brings us to our lightning round. Should be much more fun than all the heavy lifting that you have done so far. All it entails is I'm gonna ask you some simple question and I need immediate responses, okay? Alex Small: Okay. Rohit: Sweet or Savory. Alex Small: Savory. Rohit: Books or Podcasts. Alex Small: Books. Rohit: Are you more of a Thinker or a Doer? Alex Small: Hmm, I'd say thinker and that's a hard one though Rohit: Introvert or Extrovert? Alex Small: Also hard, but I'd say Extrovert. Rohit: Scotch or Whiskey, what's your guilty pleasure? Alex Small: I don't drink. So my guilty pleasure is food. I eat a lot of healthy food, but like, let's say salmon. It's a steak actually. Yeah, that's the best one. Rohit: All right. No caffeine. Alex Small: Nope, no caffeine. Rohit: Wow, very cool. How does someone impress you? Alex Small: Hmm. Someone impresses me by being intelligent and being able to apply that intelligence to doing things well in the world. Rohit: If not a strategy person, what would you be? Alex Small: If not a strategy person, I would be a business operator, potentially a salesperson. Yeah, someone on the business side. Rohit: All right. If you can be head of strategy or head of finance of any company for the day, which company would you choose and why? Alex Small: Hmm. I would probably choose Google because Google is at such an intersection of so many things in the world, that the visibility you would get from that and the learnings and seeing the maturity that they've developed over the years would be incredibly informative. Rohit: What is your ideal place to retire? Alex Small: I would say French Polynesia. Well, yeah, Bora specifically. Rohit: If you could teleport yourself right now, where would you go? Alex Small: Bora Bora, French Polynesia. Rohit: Number one item on your bucket list right now, is that also Bora Bora? Alex Small: Ooh, bucket list. I want to go to Japan. I've never been to Japan, and I would love to see the country. Rohit: All right, if you could un-invent something, what would it be? Alex Small: Hmm. Wow. So this is controversial, but maybe AI because I think that AI is increasing so many things and improving and creating so many things. And yet it is upending a lot of the things that a lot of people were building. And there's just a amount of disruption there that is almost undesirable. You know, like I don't know that I needed AI in my life. Like technological progress did, but I don't know that I personally did. Rohit: Who is your role model, personally or professionally? Alex Small: Hmm. One of the folks that I've always looked at as a role model is Warren Buffett. I mentioned him earlier. I love his leadership approach. I love what he's accomplished. I think that he is a remarkably sturdy individual that I aspire to be when I'm, you know, 90 or however old Warren Buffett is. So yeah, a lot of things I admire about Warren Buffett. Rohit: Very cool. One thing that can make you 10x more productive. Alex Small: Eating well. So part of what I mentioned, you know, no drinking, no caffeine. I also eat very healthily salmon, sweet potatoes, vegetables, you know, pretty, pretty much as healthy as it gets no butter, limited salt. And I found that I just increased IQ points. I have not measured this but I believe that I became a significantly more effective, intelligent, capable individual when I cut out a lot of the things that were causing me issues dietarily, have a lot of food sensitivities and things like that I discovered over the years. Rohit: Alright cool. The last one, describe yourself in three words. Alex Small: Hardworking, introspective, and ambitious. Rohit: Well, this has been an amazing, amazing show, Alex. Thank you so much for all your time. Really appreciated it. Alex Small: Cool. Yes. Thank you for having me. It's been a really interesting chat. Happy to have been able to share a few things. Hope it's helpful to the world. And yeah, thank you.