Ajay Vashee (IVP, former CFO at Dropbox) on Building Enduring Companies & Strategic Finance

Want a finance team that constantly pushes boundaries? Most CFOs focus on keeping the books balanced. Ajay Vashee turned his finance organization into a strategic disruption machine. The result? A team that saved 10,000 hours annually while launching company-changing projects like Dropbox's "Magic Pocket" $400 million infrastructure bet.

About Our Guest: Ajay Vashee

Ajay Vashee is a General Partner at IVP, one of the premier growth-stage venture capital firms. Before joining IVP, he served as CFO at Dropbox, where he helped scale the company from $45 million in revenue to over $2 billion ARR, guiding them through their IPO and early public company years.

Ajay's career began at Morgan Stanley in investment banking before transitioning to venture capital, where he initially focused on cleantech before expanding into software and SaaS. His nearly 10-year journey at Dropbox gave him deep operational experience in scaling finance organizations, managing strategic projects like the $400 million "Magic Pocket" infrastructure migration, and leading over 30 acquisitions.

At IVP, Ajay has invested in companies like Numeric and Figma, focusing on application software and the office of the CFO software stack. He's also the co-creator of the "Maslow's Hierarchy of Needs for Growth Stage CFOs" framework and leads the IVP CFO Collective, supporting pre-IPO finance leaders.

Insights + Quotes

Ajay shares invaluable lessons from his journey scaling Dropbox and now investing in the next generation of enduring companies. His insights bridge the gap between operational excellence and strategic vision.

"The majority of those acquisitions were talent acquisitions, which were incredibly strategic for us in that we brought a lot of our best leaders into the company through M&A." (00:00:00)

Ajay reveals how Dropbox's acquisition strategy wasn't just about products or markets—it was about accessing exceptional talent. They specifically targeted companies with high talent density and magnetic engineering leaders who had built and scaled awesome teams, even if they were smaller organizations.

"We had a very cash efficient business, and in many ways, Dropbox scaled the entirety of its business on its series A round, which is a $7 million financing round." (00:15:07)

Contrary to the common narrative about venture-backed companies burning cash, Ajay explains how Dropbox achieved remarkable capital efficiency. Every subsequent funding round was opportunistic, giving them strategic latitude rather than addressing cash needs. This efficiency was crucial to their path to profitability and IPO readiness.

"We were able ultimately to double our gross margins from the mid forties pre-migration to close to 80% after... which really opened up the opportunity for us to go public." (00:17:39)

The "Magic Pocket" project—Dropbox's controversial $400 million migration from AWS to their own infrastructure—exemplifies Ajay's approach to strategic finance. While the industry was moving to public cloud, Dropbox's massive scale made the opposite move economically sensible, dramatically improving their margins and IPO prospects.

"We would set a goal as a company, or sorry, as a finance team every year to ideate and launch one project that would have a meaningful impact on the company's trajectory." (00:28:33)

Ajay institutionalized impact-driven thinking within the finance organization. Whether it was Magic Pocket, strategic acquisitions like HelloSign, or Project Diamond (mapping ROI to every dollar spent), the finance team consistently drove projects that inflected Dropbox's growth trajectory.

"We had this team, this automation and transformation team that was always finding new ways of working and freeing up more hours for the rest of us to then focus on impact orientation." (00:30:07)

The finance organization saved 10,000 working hours annually through automation and efficiency initiatives. This created a compounding flywheel where time saved on operational work enabled more focus on strategic, high-impact projects that drove business results.

"90% plus of the companies that we meet and the companies that have been in our portfolio fail... on managing, resourcing and accountability effectively against a pipeline of new products, against an Act two, act three and beyond." (00:40:17)

From his "Maslow's Hierarchy for Growth Stage CFOs," Ajay identifies the biggest failure point for scaling companies: successfully investing in and executing "Act Two" while maintaining their core business. Most companies struggle to allocate 30% of resources to future products that may not impact the business for 4-5 years.

Links and Resources From the Episode

• IVP (00:04:10): Ajay's current firm, where he leads application software investing and supports growth-stage companies.
• Dropbox (00:03:51): Where Ajay served as CFO through their IPO and scaling journey from $45M to $2B+ ARR.
• Figma (00:24:59): One of IVP's portfolio companies where a former Dropbox Strategic Finance team member now serves as CFO.
• HelloSign (00:27:11): DocuSign competitor that Dropbox acquired post-IPO to expand platform capabilities.
• Pigment (00:48:35): Planning software company that Ajay invested in, revolutionizing FP&A similar to how Numeric transforms accounting.
• Follow Ajay Vashee on LinkedIn

Full Episode Transcript

[00:00:00] Ajay Vashee: the majority of those acquisitions were talent acquisitions, which were incredibly strategic for us in that we brought a lot of our best leaders into the company through m and a. We would target companies where, where, again, we knew talent density was super high. There was an eng, a magnetic engineering or technical leader at the company that had helped to build and scale an awesome team.

[00:00:16] Ajay Vashee: Usually a smaller team, but an awesome team. And that was the thesis behind most of our talent acquisitions. 

[00:00:21] From Numeric, this is Incoming Statements. The podcast built for forward thinking accounting pros. Join Anthony Alvernaz, Numeric's co founder and chief product officer, as he talks with accounting leaders about what practices and philosophies are defining modern financial operations. So, grab your coffee, throw on some headphones, and let's dive in.

[00:00:50] Anthony Alvernaz: Hello, and welcome to another episode of Incoming Statements. I am your host, Anthony Alvernaz, co-founder here at Numeric. And today we're thrilled to have Ajay Vashee on the show. Ajay is General partner at IVP and the Strategic Mind Behind Dropbox Journey to Public Markets. Ajay's been at the heart of a few pivotal financial strategies, a couple ambitious growth projects, and several of acquisitions.

[00:01:09] Anthony Alvernaz: Ajay, thanks for making the time today.

[00:01:11] Ajay Vashee: Thank you for having me. Super excited to be here, Anthony.

[00:01:14] Anthony Alvernaz: Likewise, let's jump in.

[00:01:16] Anthony Alvernaz: so Ajay, super excited to, to sit down today. Appreciate the time. would love to start with something highly, highly open-ended, which is, tell us your story. who are you?

[00:01:24] Ajay Vashee: That is an open-ended question. Uh, indeed. Uh, well, I, I was born and raised in, in the northwest, uh, near Seattle and. my dad worked for many years at Microsoft. My mom was a CPA, and so my origin story in many ways formed the foundation for me ultimately becoming tech CFO and then investing in companies like numeric.

[00:01:45] Ajay Vashee: So there's probably lots to unpack there over the course of our conversation, but after growing up near Seattle, I, I went to college out in New York and I, worked at Morgan Stanley. That was my first job out of undergrad, and spent a few years as an analyst in the investment banking division. I.

[00:01:59] Ajay Vashee: I had really had a great time. I learned a ton. I built some very long lasting relationships. Actually, we had our 20 year Morgan Stanley analyst reunion just a couple of weeks ago in New York. The firm was great about bringing all of us back together and we had a really strong showing, of folks that spent many long hours working together at 1585 Broadway, our headquarters in New York.

[00:02:20] Ajay Vashee: And then I left banking, to join a venture fund out in California. I had worked on a few clean tech deals. I was an analyst at Morgan Stanley, that kind of gave me some exposure to what was emerging in categories like wind and solar and biofuels. And so I initially joined the world of tech and venture to focus on clean tech investing, and I did that for really a few months before quickly expanding my focus to include the world of software and and SaaS.

[00:02:53] Ajay Vashee: And I loved what I was doing. It was this super energizing job where I was, I got to be at the forefront of everything that was happening and changing in the world, and all these incredibly exciting startups and founders. And I felt like, Hey, I, I found my calling and this is what I want to do for the rest of my career.

[00:03:09] Ajay Vashee: And I spent a few years at this venture fund and then had the opportunity relatively early on in the company's journey to join Dropbox. And I wasn't thinking. Of taking an operating role, but looking around the table as a venture investor, I noticed that a lot of the best and most impactful investors were ones that had been in the operator's shoes were ones that had helped to build and scale enduring companies and businesses themselves.

[00:03:33] Ajay Vashee: And so I felt like, hey, if I'm really serious about venture as a career path, maybe it behooves me to go and spend some time at a company and at the, we were diligence in Dropbox at the time as a potential investment. As a fund, and I've kind of fell in love with what the company was doing and where it was headed.

[00:03:51] Ajay Vashee: And ended up joining the team there. And what I thought would be a, maybe a, a one or two year stint to, check the, proverbial operating experience box before I went back to being an investor, ended up being nearly 10 years. And we should talk and we can talk much more about that. and so I spent almost 10 years at Dropbox in a variety of different roles.

[00:04:10] Ajay Vashee: was most recently CFO there through the company's IPO and first few years as a public company. And then I stepped back from that role a few years ago. To join our Series B Investor at Dropbox, which is a fund called IVP, which is where I am right now, and I help to lead our application software investing team here.

[00:04:29] Anthony Alvernaz: Awesome. Fantastic, fantastic rundown. I'm, I'm very excited to dig in a lot more on how all these different pieces came together. if we could go back to one of the first things you said here, you know, growing up in a household, one parent at Microsoft, one parent a CPA, in many ways, this is kind of the exact combination of a path that you've, found yourself in.

[00:04:46] Anthony Alvernaz: combining both of those, both of those passions, I suppose you could say. where do you think that came from when you were, when you were growing up? What did it feel like having, having parents at home, who were working in tech at the sort of forefront of, of a major tech giant and working in an operational capacity in, in a role or function that you're very familiar with.

[00:05:06] Ajay Vashee: I kind of swore that I would never end up in either of those industries. not because I, I had any negative experiences as a child, but if you know your parents are doing one thing and you wanna do something different, it was more along those lines. And you have to remember, this was, this was a little while ago now.

[00:05:18] Ajay Vashee: This was like. Pre a lot of the platform shifts that we've lived and breathed through as a world over the past few decades. So it was before the rise of the internet. It was before the mobile computing platform shift. It was certainly well before the, the shift that we're living through today with ai. So it was a little harder as a child to identify with everything that the tech giants were doing back then.

[00:05:42] Ajay Vashee: A lot of the work that, my dad was focused on was, more on the windows and office side of things at Microsoft, which were less relevant to, you know, a middle school child or an elementary school child. and then the world of CPAs and taxes were even more foreign to a young child that was not yet earning of any material income or taxable income, I should say.

[00:06:03] Ajay Vashee: So it was more like, I would say osmosis and exposure. And it felt like they were both focused on and solving some pretty interesting problems. There was no question about that. And they were really engaged in the jobs and careers that they had. So I think it had more of a, that indirect, formative experience than a direct one.

[00:06:23] Anthony Alvernaz: Yeah, certainly. do you, would you consider yourself to have been a, a, a pretty curious child? Do you remember conversations where you were trying to pull the thread on, you know, what are they doing? This makes no sense to me. it's a foreign, it's a foreign world. They live in day in and day out.

[00:06:35] Anthony Alvernaz: where did you draw on some of that osmosis? Yeah.

[00:06:38] Ajay Vashee: Yeah, that's a, it is a good question. I do remember some, some visits to the Microsoft Research Lab as a young child where we got to play around with like with a lot of the latest devices and software that the company was, was working on, or the device manufacturers they were partnering with, which was a ton of fun.

[00:06:54] Ajay Vashee: And then I gotta spend time with the gaming team there that was partnering with developers to develop, you know, to build a lot of the games that back then were shipped on things like cd, Rons to everyone. And so. There were elements of the platform that were starting to come together back then that had more of a consumer appeal that were really interesting and exciting to someone that was younger.

[00:07:14] Ajay Vashee: and thenI would say like on the, on the finance side of things, I was more analytical and, and more of a numbers person from relatively early on. And so that element of everything in the world of, of tax was. Kind of naturally interesting. Those, those two experiences did lead me. You know, my, my first internship before I joined Morgan Stanley, before I kind of launched my career in earnest, my first internship was at a tech startup in Seattle that was a mobile game developer.

[00:07:40] Ajay Vashee: And I spent a summer with 'em. It was a company called Mobis, uh, which ultimately got acquired. But, uh, that was my first foray into the world that we all, you know, live in today. We all operate in today. And so maybe there was a bit of a precursor there from the childhood into that internship. And then. I kind of came back full circle.

[00:07:58] Anthony Alvernaz: Love it. Love it, love it. Well, if we, we fast forward a bit, talk us through. That, that decision to take an operating role at Dropbox, we'll kind of fast forward all the way towards that first day on the job. and we'll again, we'll reject the proverbial, as you put it, proverbial need to spend a little bit of time as an operator.

[00:08:15] Anthony Alvernaz: what did that first week feel like when you were in that seat, seeing the growth that Dropbox had, just from a trajectory standpoint when you joined, and where some of the excitement was derived from on, on what this thing could be. what do those first, first weeks feel like?

[00:08:29] Ajay Vashee: Well, I will say as a venture investor, you have a a bit of an unfair perspective and lens on everything because you're seeing so many companies and they're at different stages of their growth journey, and you're doing a whole lot of benchmarking and you're building a lot of context. So. You have a good sense for which companies are truly inflecting on a one, a first percentile kind of trajectory.

[00:08:49] Ajay Vashee: And Dropbox was certainly fell into that category at the time. And so I felt like it was really on a special path in a way that almost no other company at the time was. And when I joined, this was my, this is really my first operating role in Earnest. I, I had that internship briefly that I mentioned before.

[00:09:05] Ajay Vashee: But I never really worked as an operator before. I'd worked in investment banking and investing, but never in operating. And so a lot was new, A lot was more, it was foreign to me. The pace at which we were operating was, completely at, I would, I would call it a breakneck, you know, pace where we were all trying to do many different things and we would get to the office at, in nine or 10 in the morning.

[00:09:29] Ajay Vashee: And as, as you know, in your role as an operator and a founder today. You know, leave at midnight or well beyond midnight many days as well. And we'd spend a lot of time together working incredibly hard and team building and helping to scale the company. And then we'd spend a lot of time together socially as well, because the company, in many ways, that was your job, but that was also your family, just given the intensity of work and the time that we spent together.

[00:09:55] Ajay Vashee: So. It was the first week or so was, it was, I, I would call it an overwhelming experience, but in a, in, in more of a good way. Not in a negative way. It wasn't like, oh my gosh, what have I done? It's like, oh my gosh, this is completely different than what I've been doing, and wow, I'm learning so much. I'm challenged.

[00:10:11] Ajay Vashee: It's so stimulating. It's so exciting. So in those first few weeks, I kind of felt like, wow, this could be what I do for a very long time, if not forever.

[00:10:19] Anthony Alvernaz: So some formative sort of cultural, cultural norms on the ground there, it sounds like. How did that influence, how, as you, your, your journey into becoming the CFO at Dropbox, how did that influence how you thought about, building teams and, just generally keeping pace and tone in the, the office of the CFO?

[00:10:39] Ajay Vashee: Yeah, that's a good question. So my first role, just to, just to provide some context, the Dropbox was not formally the CFO role. We had a very small finance organization when I joined a, a really two or three folks on the team. And my first role was, and mandate was to help build and scale federal organization.

[00:10:54] Ajay Vashee: So it was more of a, a head of an early head of finance. Role at the company. And I got to, it was, it was instrumental in me building the context I did to ultimately step into the CFO role because I got to help us build and scale the accounting function and then move on and build and scale the fp and a function and tax and treasury and real estate and workplace services and ultimately corp dev.

[00:11:13] Ajay Vashee: So I got to touch every part of the finance organization and help us really get those sub-functions up and running. And one thing that I noticed early on during my time at Dropbox that really. Permeated my hiring philosophy and influenced my hiring philosophy was the talent density of the company. And Dropbox at the time had a, was renowned for having really the best engineering team in Silicon Valley.

[00:11:38] Ajay Vashee: the, best regarded, highest performing, kind of most elite engineering organization. And the company was primarily RD in engineering at the time. And so we were about a hundred employees, of which the vast majority. Where it fell under the r and d umbrella. And so because the talent density there was so high, that influenced how Dropbox made its first hires and other functions like with me and finance and BizOps and sales and marketing and many other parts of the organization.

[00:12:07] Ajay Vashee: And for us, maintaining that talent density was a really important principle. We felt the pressure to do that and we saw the importance of doing that. There were, there were really two reasons. And so as I built up each function under the finance umbrella. That focus on talent density was really paramount to me as a leader.

[00:12:25] Anthony Alvernaz: Where do you feel like that? Rather, how do you feel like that funneled into the just evaluation of candidates and, and how you made that sort of mutual assessment of fit as, as part of some of that philosophical resolve?

[00:12:40] Ajay Vashee: I would say it happened a a, a few different ways. One is you got a sense for the caliber of people around you and the type of team that you were expected to build. There was a certain bar that you, that you honed over time and so you got a good, you. You had to become aqui quickly, become a, a really strong judge of talent or you wouldn't really survive in an environment like that.

[00:12:59] Ajay Vashee: So part of it was survivalist on that dimension. Then the company was great early on about, about finding systematic ways to scale culture and our co-founders back when I joined, like, I'm sure you and Parker and the team do at numeric. I spent time interviewing every single candidate that we hired, every single person that we hired.

[00:13:17] Ajay Vashee: 'cause we were at a scale where we could still afford to do that. One of our co-founders ar Ash Owie, who was our co-founder and CTO for many years, uh, did that until we got to many, many hundreds of employees, I think close to a thousand employees. He was still interviewing every new hire at the company and ensuring that they fit, you know, his mold of what the bar was at Dropbox and that that allowed us, I, I think it was a combination of the two of hiring managers being held.

[00:13:43] Ajay Vashee: To a really high standard on talent, and then folks like Arash and people that were close to him that could substitute in for him when needed. Ensuring that culturally and from a a, a talent perspective, they felt like we were checking the right boxes too. So it ended up scaling again to, to about a thousand people for us, a thousand employees.

[00:14:02] Ajay Vashee: Beyond that, you just have to come even more programmatic and systematic about how you manage hiring, and I think you kind of lose a little bit of that as you get larger and larger. Your ability to hold onto that kind of talent density naturally. It just happens. It's a bit of the law of large numbers phenomenon as it relates to people and talent.

[00:14:17] Ajay Vashee: but until then, it worked really well for us.

[00:14:20] Anthony Alvernaz: Tremendous. Well, let's talk a little bit about tactically, what worked well and what or where you found yourself potentially challenging some conventional wisdom, from the perspective of, of decisions that you were making. What felt most contentious as, as you were nearing? Nearing IPO as things were, things were heating up, profitability was not something that was necessarily explicitly being optimized for where were you most challenged?

[00:14:44] Anthony Alvernaz: I.

[00:14:46] Ajay Vashee: Well, I'll, I will just, I'll challenge you on one thing, on, your statement on profitability, which for us as a company, it, it was, I think you're right in that it wasn't something that we were very focused on, but that's because we didn't need to be very focused on it. We had a very cash efficient business, and in many ways, Dropbox scaled the entirety of its business on its series A round, which is a $7 million.

[00:15:07] Ajay Vashee: Financing round and every other round after that was opportunistic capital to bring in at relatively low rates of dilution so that we had the strategic firepower to do what we felt we needed to do. We had the latitude, the strategic latitude to do what we needed to do. and so the business was free cashflow positive very early on in journey.

[00:15:24] Ajay Vashee: there were moments in time that we, that we moved the dial and brought the business to free to free cash flow negative and really ramped up CapEx. but that was, with line of sight and, and intention to really improve margins over time. So highly efficient and in many ways cashflow positive and profitable business from its early days.

[00:15:42] Ajay Vashee: but a focus on continuing to hone that engine and improve its output. Heading into the IPO, I'll give you a couple of interesting anecdotes and stories maybe of the way that we, as a finance organization, we're really focused on impact. And how we could help to inflect and shape the business and change.

[00:16:00] Ajay Vashee: its, trajectory. So the first, there was a big project that we launched in conjunction with our infrastructure team, and we called it at the time Magic Pocket. And it was a, a, an effort to migrate off of the public cloud onto our own infrastructure. So off of Amazon Web Services, which was a great partner to us in the early days.

[00:16:20] Ajay Vashee: And we really couldn't have started the company and gotten it to scale up without. A public cloud provider like that, but to migrate off of Amazon Web services to our own internal custom built infrastructure for a few different reasons. There was a strategic rationale just around controlling our own destiny as, as a file sync and share company cloud storage provider is really important that we own what was core to our DNA, which was, how we store and serve our customers information, our user information.

[00:16:43] Ajay Vashee: And so there was that strategic rationale. there was a, a performance rationale as well, just so we could fine tune. Both the software and hardware elements of our stack to better serve our customers. So if you're sitting in Korea and you wanna play a video that's stored on Dropbox, it doesn't take 25 seconds to buffer.

[00:16:59] Ajay Vashee: It takes, you know, a milli, a few milliseconds to buffer. Um, and so that was an important reason. And then finally, from a finance perspective, and this was our contribution to the project, there was the economic rationale to this migration and. our margins as you would imagine as a company that was scaling as quickly as we were and with, with customers and users storing more and more data over time.

[00:17:19] Ajay Vashee: As they took more photos as they brought Dropbox to work. Our margins were something that we were spending a lot of time thinking about and, and managing and projecting, trying to optimize. And by fine tuning that hardware software stack and migrating off of the pub, the public cloud, we were able ultimately to double our gross margins from.

[00:17:39] Ajay Vashee: The mid forties pre-migration to close to 80% after, you know, a, a post-migration, uh, which was, which is huge as you know, from the world of finance and gross margins. And that really opened up the opportunity for us to go public, because we had a, a real software, gross margin and financial profile and a more compelling, you know, narrative to bring to market at the time.

[00:18:01] Ajay Vashee: and so that, so it was a huge project. It was a very controversial one. At the time too, because the rest of the world was moving from their own infrastructure to the public cloud because economics made much more sense in that direction for the majority of companies out there. But for us, because we were storing exabytes, literal exabytes of data, we were at the scale where it made more sense and we could realize more economy scale by going the opposite direction.

[00:18:20] Ajay Vashee: It was also controversial because of the cost of the project, and again, because we were managing such a large storage footprint. And then if you add in duplication on top of that, it's an even larger footprint, multiple times that. Um, it was a $400 million capital investment as a private company at the time, which is a whole lot of capital and, uh, made a whole lot of our investors pretty nervous around, Hey, you're doing the opposite of, of what the rest of the world's doing, and you're spending close to half a billion dollars to do it at a time when no one was raising that amount of capital.

[00:18:49] Ajay Vashee: but it was strategically, it was the right move for us to make and it really opened up the ip, the both the IPO opportunity and the opportunity for us to build a company that we did.

[00:18:56] Anthony Alvernaz: So something that's such a large driver to gross margin like that, it's really, it is an incredible story and, and, and comically controversial in some ways. o obviously a lot has to come together for that to be something that, that overall the, the teams even get motivated around, around doing. I. Sounds like there was value in the sort of data ownership and the, the company values at the time. There was clearly some impact on the product experience, that sort of availability for different regions. but it does sound clearly like the financial impact here was, a major, major driver.

[00:19:23] Anthony Alvernaz: How, what did that look like on the ground? how driving that sort of consensus across teams for everyone, obviously who would have to be involved to make it successful, to get really excited about prioritizing it as a major effort. and then to what extent was there additional staffing and how that, how did that work around, around making the project actually something that, that could be executed in, in a timely way without, you know, major downtime or, or other risks.

[00:19:48] Ajay Vashee: Yeah, it was a multi-year project, I will say. So it took a long time, and that was very deliberate and intentional to manage it on a multi-year timeframe so we could slowly ramp, up our own infrastructure footprint, and then we had to mirror for a period of time, every piece of data, every piece of user data and customer data, both on our own infrastructure.

[00:20:04] Ajay Vashee: As well as on the public cloud. And then over time we could reduce that, that public cloud footprint after we migrated and mirrored for some period of time and felt comfortable. and so it was a very complex, multi-year project. I think the team was super motivated to do it though internally from really from day one because the rationale was so clear across those three dimensions that I mentioned before, the strategic performance and economic rationale.

[00:20:26] Ajay Vashee: It was. It was so clear and that rationale touched every part of the company in a different way. You know, the strategic rationale mattered so much to our board and to our executive team at the time. The performance rationale, if you think you know yourself as a sales rep or someone working in customer service or support, they were super excited about that.

[00:20:43] Ajay Vashee: The financial rationale, the finance team obviously got very excited about, but the whole company did too, because it was something that was gonna open up the opportunity for us to build an even bigger and more powerful business and open up the opportunity for us to ultimately go public as well, which was something that the company.

[00:20:57] Ajay Vashee: at the right point in time was, was really excited about doing.

[00:21:01] Anthony Alvernaz: Fantastic. Did you ever feel like there was there a moment in that multi-year project where. keeping folks just aligned on what the overall goal was extra important in, in terms of, just the level of effort required over, over a long period of time. Like, how do you keep pace?

[00:21:15] Anthony Alvernaz: How did you find that that pace was kept on, on a multi-year project like that?

[00:21:20] Ajay Vashee: I think this, this comes back to, to talent density without question. And it comes back to like one really interesting, Derivative of talent density, which I'll get into, which is like a, a new team that we started within the finance organization that hadn't really existed before, but maybe starting with talent density at large.

[00:21:37] Ajay Vashee: our, our infrastructure team was really incredible and it was led by a leader named Hil Gupta, who's now a VP of engineering at Databricks. but he, he attracted the best infrastructure talent in the world from the likes of. The Microsoft Azure team and Amazon Web Services and GCP, and he assembled that team very deliberately over a period of time.

[00:22:01] Ajay Vashee: And then, this is the team that had the only team in the world, the only people in the world that actually had the experience building a storage and compute infrastructure footprint to the scale that we had to were these people because they had worked at the hyperscalers and outside of the hyperscalers at the time, no one else had experience like this.

[00:22:15] Ajay Vashee: So I think having that level of talent with that kind of experience was. Super, super important. And then we had to compliment that on the finance side of the house too. And there wasn't really a, a nimble, agile finance organization that had supported this kind of a project at a startup before. So we had to build that.

[00:22:33] Ajay Vashee: And that team was called Strategic Finance. And it was one of the first organizations that I launched. In fact, it was the first team that I started after joining Dropbox before focusing on accounting and fi and fp a and other more traditional functions. And this was a team of really high H, high horsepower generalists.

[00:22:47] Ajay Vashee: That we hired out of investment banking and investing programs, out of management consulting. And so think about folks who would like, like me early in my career track who were building a career in venture, perhaps private equity or at a hedge fund, or they'd worked in management consulting for a while and then were working, spending time with a client.

[00:23:05] Ajay Vashee: We kind of pulled both the best people from those ca those industries out. And convince him to join Dropbox on the strategic finance team. And it was like, it was a foreign career path for a lot of them at the time. They were like, wait, wait, I'm gonna work at in-house at a company on a finance team.

[00:23:20] Ajay Vashee: That's not something that I had envisioned myself doing. Like, is that really the right career path for me? I thought that's like more, if I had an accounting background or I, I wanted to be a career fp and a lead, a professional or leader, that's not me. And we convinced 'em to join. but they were, and we ultimately brought maybe.

[00:23:36] Ajay Vashee: 10 or 12 folks into that organization early on, and they had such incredible impact. They were the team that partnered with infrastructure to manage this migration. They were the team that helped to ideate and launch new paywalls for Dropbox. That allowed us to monetize more of our business users more efficiently over time.

[00:23:52] Ajay Vashee: They were the team that helped us scour the acquisition landscape and D you know, determine what would make sense from a talent product business m and a perspective. When I was at Dropbox, we acquired over 30 companies, and so we were highly acquisitive. they were the team ultimately many years later that helped lead us over the threshold of gap profitability.

[00:24:11] Ajay Vashee: So, it was a really powerful organization and it was, again, in the, spirit of us talking about talent density earlier, it was a team that could really hold its weight against any other part of the organization at Dropbox.

[00:24:23] Anthony Alvernaz: Which I'm sure very crucial for, for folks who, who have to be tasked with partnering with, with everyone across every team. So totally, uh, totally makes sense. Certainly, certainly resonates with how we, how we think about building just groups of people who you're really excited to work with, no matter the function and, and keeping that true across, across the org.

[00:24:39] Ajay Vashee: I was gonna jump in and just say one thing. I'll make a quick plug, which is that that strategic finance alumni group has gone off to do incredible things and, They're really amazing leaders out there in the world of, of, of tech and finance more broadly today. but I, we are close to having our first strategic finance alumnus take their company public as CFO.

[00:24:59] Ajay Vashee: And so one of our other portfolio companies here at IVP we're very proud investors in numeric, but we're also proud investors in, Figma. And that was the first investment that I worked on after joining the firm back in 2021. And Figma announced that they had filed to go public and. they're hoping to get out at some point here, but the CFO at, at, Figma per, was one of the first hires into the strategic finance organization at Dropbox.

[00:25:19] Ajay Vashee: So we're starting to see that alumni group to our conversation on talent density now start to go off and lead their own companies and take those companies public, which is so, it's so inspiring to see

[00:25:29] Anthony Alvernaz: Certainly, yeah, de definitely some, some foundational principles, I'm sure on that team that, maybe on another episode we'll have to get further into and, bring veer into the conversation as well. I would love to, get more of that perspective. when you think about just some of the, some of the other aspects of what you worked on at, at Dropbox.

[00:25:44] Anthony Alvernaz: You mentioned a couple times notion of corp dev acquisitions. talk me through how did that. Philosophy unfold. how did you think about the approach 30 plus companies? Pretty large number where were some of the more complex strategic bets?

[00:25:59] Ajay Vashee: That is a great question. So the, the majority of those acquisitions were talent acquisitions, which were incredibly strategic for us in that we brought a lot of our best leaders into the company through m and a. We would target companies where, where, again, we knew talent density was super high. There was an eng, a magnetic engineering or technical leader at the company that had helped to build and scale an awesome team.

[00:26:17] Ajay Vashee: Usually a smaller team, but an awesome team. And that was the thesis behind most of our talent acquisitions. And then from a product perspective, there was sometimes a product gap that we were looking to fill. There was a new category that we were looking to extend into and where perhaps we wanted a head start by making the right product acquisition.

[00:26:36] Ajay Vashee: I think we learned the hard way on a few of those that it's, it's more difficult than you might anticipate to truly integrate a new product into a larger platform that you built. And then on the business front. There were some natural adjacencies. If you think about Dropbox, it's, it's the home for the world's information, most important content and information.

[00:26:57] Ajay Vashee: And there are many actions that users and customers want to take with that information. And so the more we can help them with that, with the workflow around the content they're storing and sharing with Dropbox. The more, the more valuable the platform becomes, the more we can do for our users and customers.

[00:27:11] Ajay Vashee: And that was the thesis behind the, some of the business acquisitions that we made. post IPO, one of the deals that I, helped us with and we, at companies we acquired as a company, called HelloSign. And it was, it was a competitor to DocuSign focused a little bit more on the SMB market, which is where more of the business footprint was at Dropbox.

[00:27:28] Ajay Vashee: but it was something that we could turn on for all of our users really instantly and integrate into the platform. And so. That was a thesis behind some of the, the business acquisitions, that we made as a company.

[00:27:37] Anthony Alvernaz: I've heard you describe yourself as a growth oriented CFO and, and certainly this, this concept of looking at adjacencies, you can expand into getting head starts. A lot of the corp dev acquisition angle feels very much in, in that camp. Where else does that growth minded CFO concept come into play most?

[00:27:53] Anthony Alvernaz: how do you kind of characterize that philosophically for, how you steered the ship at, at Dropbox?

[00:27:59] Ajay Vashee: That's a good question. Most of my time was spent on, on growth oriented projects. That's naturally where I derived the most energy and where I tried to focus the organization. I'd probably caveat that now by upon reflection and say it was more of an impact orientation than it was necessarily only a growth orientation growth, like business growth orientation.

[00:28:20] Ajay Vashee: It was a business impact orientation, like now growth mindset and a learning mindset, and. Ensuring that the organization was scaling in the right way and that our leaders had the access to the right level of talent development and coaching. All that growth was really important, but maybe just focusing on business growth and business impact.

[00:28:33] Ajay Vashee: It was really an impact business impact orientation, and we would set, to answer your question, we would set a goal as a company, or sorry, as a finance team every year to ideate and launch one project. That would have a meaningful impact on the company's trajectory that would inflect Dropbox's trajectory.

[00:28:52] Ajay Vashee: And one year it was Magic Pocket. the project that we talked about to migrate off of AWS another year it was this acquisition of Hello Sign that we just talked about another year. It was a project called Project Diamond, which was a couple years after our IPO, which was an effort to really map an ROI to every dollar spent as a company, whether that, was, performance marketing spend, which traditionally.

[00:29:12] Ajay Vashee: It has, you know, uh, an established set of frameworks to measure and manage, or it was like legal contract spend or team building spend or t and e. How do you assign an ROI to all the spend and like, why are we engaging in it? And that ultimately allowed us to pull back on areas of inefficiency with that compromising our long-term growth aspirations or potential to cross the threshold of profitability.

[00:29:31] Ajay Vashee: So every year it was a project like this. And then in parallel with the impact orientation projects, as part of our philosophy as a finance organization. Every year was also a focus on continuous improvement and automation. And, we would have a goal every year of saving 10,000 working hours as a team through automation and efficiency initiatives.

[00:29:52] Ajay Vashee: And that'll, that forced us to really scour the landscape of all the next generation tooling out there. Both what we could buy, but then also to partner with our internal tooling team on what we could build to really have the team operate more efficiently. And then it became this flywheel where like, we have this.

[00:30:07] Ajay Vashee: We had this team, this automation and transformation team that was always finding new ways of working and freeing up more hours for the rest of us to then focus on impact orientation. Even more. Even more, even more. So every year it compounded and every year we got more effective and we got, and we became more impactful as a finance organization over time.

[00:30:26] Anthony Alvernaz: There's certainly a never get too comfortable, never be willing to, to ask why or, or what could be done differently. Philosophy that you, you have to ingrain as true for, for that to work. I, I, I'd like to zoom in a tiny bit on the, this, this notion of the transformation and, and automation team. how did, how did you organize that team around being.

[00:30:43] Anthony Alvernaz: Being able to, to sort of prod and push at what other folks were working on and, and really draw out where there were opportunities, to make real improvement.

[00:30:52] Ajay Vashee: Yeah, that team was started, it was started by our, at, at, at the time, chief Accounting Officer, and controller, who's now CFO at Dropbox and has done a, a phenomenal job. but so I, I owe all credit here to Tim Regan, for the. The transformation team, the automation transformation team. But that team built a very, very keen and deep understanding of exactly how the finance organization worked, every element of the organization and what everyone did.

[00:31:17] Ajay Vashee: The tooling that they were using today, how, or, or they weren't using what was being done, done in Excel and manual workbooks where we were using systems and tooling. how old that tooling was, the rate of change in development, the kind of collaboration between our org and other orgs, and how we managed that.

[00:31:33] Ajay Vashee: So. They had a really, they were, it was led by folks who had been at Dropbox for a very long time, who had been there for, when we launched a team probably close to seven or eight years, and who had spent their careers in finance and so who had a really good sense for how a lot of this worked. And for them it was like, it was a super energizing project and team to manage on an ongoing basis because it was a break, a departure from the normal and from the, the traditional career path that they were on.

[00:32:00] Ajay Vashee: To focus on something that, again, there was really no other team that we could find in the valley that was focused on this in the same way. So it was a totally novel exercise. And then, and then what began is what we thought would be like kind of a one time consulting project for this team to figure out what we could improve became this exercise in continuous improvement where we never really stopped and go ahead.

[00:32:22] Anthony Alvernaz: No, no, I just, just wanna interject and just continuous improvement obviously implies not all efforts succeed. There, there are plenty of failures and fast learning. curious how to what extent, if at all there was any I. any challenge with, with how to balance that really open willingness to failure and improvement with, other aspects of, of the financing accounting function where accuracy, precision, you know, you worth going the extra mile to not have a failure is more the mode to, think about or operate in.

[00:32:48] Anthony Alvernaz: or do you challenge that entirely and kind of think about that fast failure as something that should be endemic across the, the entire org.

[00:32:56] Ajay Vashee: That is a great question. we set up. So I'll, I'll answer that two ways. One, how we manage that in the finance organization, and two, how that was informed by our culture as a company. Maybe I'll start with the first though, which is, as a finance organization, we had two core operating principles that I set.

[00:33:11] Ajay Vashee: One was this principle of continuous improvement. The second was this principle of strategic disruption, which, kind of correlates to that impact orientation. I was talking before and we have an award every quarter, the continuous improvement award and the strategic disruption award. And we had teams, like, we had multiple projects that were running after each, every quarter, and teams were just clamoring and working overtime just to make sure, you know, to, to see if they could win the award.

[00:33:33] Ajay Vashee: The

[00:33:33] Ajay Vashee: award, 

[00:33:34] Anthony Alvernaz: competition.

[00:33:34] Ajay Vashee: exactly. It was, was something, you know, relatively, it was like an Amazon gift card or something relatively basic, but it was more the, the, you know, the, the pride of helping to move the organization forward in a really meaningful way that matter to people. And then as you said, the competition as well, so.

[00:33:49] Ajay Vashee: We had a lot of projects that didn't really move the needle and didn't have impact, and we had a lot that did. and we celebrated the ones that did, and we celebrated the pipeline of projects that was always out there in development, in production. So I think people quickly got accustomed to this idea that like they should swing big and it doesn't matter if that project doesn't quite make, you know, cross the threshold and hurdle of, of going live and having a real impact because next quarter's rolling around and you have this pipeline of the next 10 things you're gonna work on.

[00:34:17] Ajay Vashee: And. One of them's gonna hit over time. That's the, you know, my answer for us as a finance organization. Now, that was informed by our culture as a company where we made a lot of product bets early on, and some of them panned out, some of them didn't. And it was a culture of, of, of building and failing and learning from your mistakes and moving on and doing the next thing.

[00:34:38] Ajay Vashee: In fact, I remember this vividly, this conversation. It wasn't long after I joined. We had raised, I joined when we were closing our series B, and we followed up our series B with an employee tender to offer employees some liquidity. And in that tender we brought in Fidelity, T Row Price, Morgan Stanley, investment Management, Wellington, and a couple of hedge funds into that tender offer and one of the legendary public market investors that came in as part of that mutual fund cohort.

[00:35:09] Ajay Vashee: Was someone named Will Danoff, who's still a very active investor at Fidelity. And part of the investment thesis or the pitch that we had when he came into the tender was around this multi-product strategy. And we were just acquiring this company called Mailbox to get into email. And we were launching a photo sharing app called Carousel so you could share all the photos that you had stored on Dropbox.

[00:35:31] Ajay Vashee: And it was gonna be this, like this multi app strategy where like the core Dropbox app was. In know front and center. But then we had built this constellation of tools around it. Well, we ended up sunsetting mailbox. We ended up sunsetting carousel because we weren't seeing the right level of product engagement, um, for us to continue to funding these, these initiatives and a handful of other bets that we had made.

[00:35:53] Ajay Vashee: And I remember like having to call, well, Danoff and I was so nervous. I was like, oh my God, I'm gonna call this like legendary public market investor who ultimately would like be the one anchoring our IPO if we go public and tell him that. The whole pitch that we gave him was bogus and we're sunsetting 90% of the products that we were talking about.

[00:36:10] Ajay Vashee: And so I, I remember getting on the phone, I was like, will, like, hey, just, just wanted to update you. Like you're gonna see this in the news. Like, we're sunsetting carousel, we're sunsetting mailbox, we're sunsetting X, y, Z. And he was like, mm-hmm. Mm-hmm. Mm-hmm. And he goes, he's like, and he goes, okay, what's next?

[00:36:22] Ajay Vashee: And all he cared about was, what are you building next? What's next in the pipeline? What should we be excited about? He didn't care that we were sunsetting, you know, in fact, it was ordinary course of business for will. That like to be expected, you should be sunsetting products because everything you launch is not gonna be, have the same level of success and electric product market fit is core Dropbox.

[00:36:41] Ajay Vashee: You're gonna have to earn your way to act two and act three and act four and beyond. So I think that became part of the culture relatively early and as we, and, and we learned from others that like, Hey, it's okay to fail and then it, it permeated every organization, you know, including finance, like we talked about.

[00:36:59] Anthony Alvernaz: I, we can't, we can't, we can't have a conversation here without switching gears a little bit into your Maslow's hierarchy of, of CFO needs breaking some of these financial dogmas, I feel like, some might consider it a bit unconventional and we're sort of, at least from my perspective, we're kind of in an act two in your, in your hierarchy here of platform expansion, new products and, and when to say no in this context to new products or sunset them.

[00:37:20] Anthony Alvernaz: But can, can you give us a little overview on, on that philosophy? What, what that all means. and we'll dig in a bit there.

[00:37:26] Ajay Vashee: Yes. so the Maslow's Hierarchy of Needs for Growth State CFOs is something that we shared. I shared with my colleague, former colleague, Michael Meow. Also X Dropbox Strat fan, join me at IVP and now he's c, he's CFO at Glean. But he and I launched a, a these set of dinners and meetups for CFOs in IPS portfolio.

[00:37:45] Ajay Vashee: So maybe quickly to transition from Dropbox to IVP, two and a half years after we went public, I passed the reins. I mentioned Tim Regan earlier, our former Chief Accounting Officer to Tim and join the team here at IVP. and I loved being a CFO and it was really important to me. To continue, to kind of cultivate the CFO community and a lot of the energy, from that.

[00:38:07] Ajay Vashee: And so, I set up relatively early on with Michael, something called the I-V-P-C-F-O collective. And it was a group, it was a community for kind of pre IPO, private growth state CFOs. It's what I kind of wish I had when I was CFO at Dropbox. I stepped into the role for the first time. I was a first time CFOA relatively young one, hadn't done the job before.

[00:38:27] Ajay Vashee: I could have really benefited from having a network of folks who were. On the same journey as me and a few steps ahead of me as well, to learn from. And so that was the impetus behind pulling together the, the, the CFO collective. Our, at one of our first dinners for the CFO Collective, we walked through this concept, the set of advice for all the CFOs in our portfolio called the Masses Hierarchy for Growth State CFOs.

[00:38:50] Ajay Vashee: And it's a multi-part pyramid, like massive's hierarchy. We can probably share the graphic. with folks that will be tuning in to, to listen and watch here, but at the bottom of the pyramid is this concept of runway For a growth stage. CFO, the number one priority needs to be runway. Without runway.

[00:39:05] Ajay Vashee: There's, there's really no future. You can't fund your business. and understanding and managing cash runway is one of the most important responsibilities of A CFO at the growth stage. So that forms kinda the basis of the pyramid. Um, and then runway allows you to invest to structure a durable core business.

[00:39:21] Ajay Vashee: That's the next stage. Or the next layer of the pyramid rather. Um, a durable core. So one that you can continue to efficiently scale. And this is where, like, this is where I would say most companies at their growth stage are focused. They have a reasonable amount of runway, they've been successful at fundraising.

[00:39:36] Ajay Vashee: They found product market fit. They're starting to scale things up, but they're focused on structuring a durable core business. They're burning a lot of cash. They're still building out that, the capital intensives go to market organization. AEs aren't quite ramped up. So, you're in burn mode and you're trying to get to a repeatable, scalable place That's like the second layer of the, of the pyramid.

[00:39:56] Ajay Vashee: And then the third is, premise on, on runway, allowing you to invest in what's next. So as we've kind of talked about today, the best companies, are the ones that are really focused on resourcing and managing accountability against the needle moving Act two. And so that's something that pipeline of projects, that pipeline of new products is something that the best companies are always cultivating.

[00:40:17] Ajay Vashee: This is where, honestly, I see 90% plus of the companies that we meet and the companies that have been in our portfolio fail, which is on managing, resourcing and accountability effectively against a pipeline of new products, against an Act two, act three and beyond. And it's so natural to really focus on the core of what you're managing.

[00:40:44] Ajay Vashee: And you, and as a, a startup employee or a founder, you're just trying to survive to fight another day in many ways too. And so it's really hard to have the wherewithal to take 30% of your resourcing and allocate it to something that may or may not succeed and will not have a business impact for four to five years.

[00:41:02] Ajay Vashee: That, that takes a lot to do that. But the best companies do do that, and that allows 'em to, to really. Accelerate their journey to becoming a platform company and a business over time. And also like when they're, when they're ready to go public or perhaps work through an acquisition, they have multiple products that are monetizing a much more powerful narrative, higher NDR, happier customers, higher ACVs, more efficient sales site, a much more efficient sales engine.

[00:41:27] Ajay Vashee: And so, it's really important to start making those investments early. That's the, the third layer of the, of the pyramid. And then there's Gap Pro. There's like profitability. We talked a bit about it earlier. I mentioned this project called Project Diamond. That is a project that we launched two years after going public.

[00:41:44] Ajay Vashee: It was the last project that I managed as CFO 'cause it was important for me to, for us at that time, to cross the threshold of profitability. but that can come for us, came years after our IPO and I think there's been like a little bit of a seesaw in the world of, in the e like the private tech ecosystem over the past few years.

[00:42:04] Ajay Vashee: And I think some investors and some companies over indexed on profitability too early. And it's like, Hey, hey, like we gotta focus on profitability. When are we gonna be profitable? When are we gonna be free Cash flow positive. And I think if you don't manage that thoughtfully, you end up in the trap of.

[00:42:18] Ajay Vashee: Under investing in the business, under investing in your pipeline of products, under investing in act two. So that's kind of the master hierarchy and and companies that I would say in our portfolio that we've seen follow that path of like really being diligent about managing cash runway, structuring a durable core business appropriately, managing, effectively managing execution, accountability against act two, and then focusing on profitability at the right time.

[00:42:42] Ajay Vashee: Those are the companies that really become enduring market leaders, have very successful IPOs. Continue scaling market cap in the public markets, it's, it's a path we've seen really drive a lot of success.

[00:42:52] Anthony Alvernaz: Where do you feel among that, among that path? we talk a lot a a lot about that sort of act two being, being hard to place, you know, the right bets in the right places. but when we think about the durable core business aspects, where do you feel like folks often, often struggle there? when there are signals of product market fit, they're on a journey of growing a RR.

[00:43:11] Anthony Alvernaz: any common pitfalls that you feel like, folks overlook when they're starting to scale some of that?

[00:43:17] Ajay Vashee: Well, there's a few. One I'll mention is like there's, there's a very common pitfall of leaning into relatively inefficient marketing spend, and so if you don't have the right fidelity and instrumentation and finance marketing partnership, I think you'll often, it's too tempting for companies that are at the growth stage.

[00:43:35] Ajay Vashee: To really lean, to lean into growth at all costs, and then lean into spend that is not durable and is not scalable. And all of a sudden you see CACs start to rise relatively quickly. You see l LTVs start to come down because churn rates are higher and you end up in an a, a position that's not sustainable.

[00:43:54] Ajay Vashee: So that's, that's a pitfall that we see pretty often as investors. And then I would say, the durable core is the, there's a tam constraint that we see as well from time to time, which is there's an assumption that, hey, like a, any application software business in theory or any infrastructure software business in theory should be able to get to hundreds of millions or billions of a RR over time.

[00:44:17] Ajay Vashee: And so it's a question of how we a architect that path to get there. And we see a pitfall of companies occasionally, you know, fall into, which is, hey, like. We should be able to get there because this peer company that we comp ourselves against got there. When in reality you're serving a much narrower segment of the market, a much narrower slice of the market, and the TAM really isn't there to support it.

[00:44:34] Ajay Vashee: So it's really some of those TAM constraints. And then, you know, the, the marketing spend that we can see create issues for companies on that, on that durable core.

[00:44:42] Anthony Alvernaz: Mm-hmm. Mm-hmm. When you think about some of that, some of those learnings, some of that, some of those observations that you have, in the ways companies start to scale just more broadly, we would love to understand the transition back into an investor role at IVP, achieving a significant milestone at Dropbox.

[00:45:01] Anthony Alvernaz: what personally drove you there? What do you think was the, sort of aspect of your own aspirations that, that, that most keenly had you saying this was the right next step after post IPO?

[00:45:14] Ajay Vashee: That is a great question. I, there were a few different reasons. One, I would say I, I really enjoyed being a CFO and. I learned a lot being a CFO and, and in many ways because it was my first time doing the job and I was really challenged and stimulated and I had to grow and I had to show up for the company and my team, and I wanted to be back in that position again where I felt, you know, where I, I could try something new and I would be challenged and I'd have to grow and develop a new muscle.

[00:45:43] Ajay Vashee: And so like I didn't want to go be a CFO again and I wanted to go do something different. so that was a big reason. Another reason is I. It was reflecting on the growth journey that we had been on during my time at Dropbox. And when I joined Dropbox, I mentioned we had about a hundred employees. We were at about, we had just done 45 million in gap revenue the prior year, and the growth journey was growing from a hundred employees to 3000.

[00:46:05] Ajay Vashee: It was growing from 45 million in revenue to 2 billion in a RR. It was private to public, single product to multi-product. It was kind of the quintessential growth journey that we want all of our portfolio companies as growth investors to be on. So I felt like. I had recent, ex recent and relevant experience that I wanted to lean on for the benefit of the next generation of potentially consequential companies.

[00:46:27] Ajay Vashee: and then I wanted to stay like an integral part of the tech ecosystem, and so I didn't wanna stray too far from that. And so how do I marry those three things about, you know, staying challenged and staying motivated and, and staying within the broader umbrella of the tech ecosystem.

[00:46:43] Ajay Vashee: and it felt like a return to investing would be, was gonna be the best way to do that. And so that led me to talk to the folks on our cap table at Dropbox that I'd gotten to partner with as an operator. and then led me to IVP where we focus really exclusively on companies at the growth stage.

[00:46:58] Ajay Vashee: Who found product market fit, who were in the early innings of scaling, go to market, who have aspirations to go public, who are on that journey, from single product to multi product who are thinking about that act to everything that we walked through today. Like, that's the kind of company that we invest in, like numeric.

[00:47:10] Ajay Vashee: and it's been an incredible job since then. I've gotten to invest at, the application layer during one of the most consequential platform shifts that, or perhaps the most consequential platform shift any of us have lived through. And I also get to invest in companies that are near and near to my heart, like numeric that are serving the office of the CFO software stack and really helping to revolutionize that in a way that never existed when I had my transformation and automation team years ago.

[00:47:32] Ajay Vashee: Never existed in the category for the past few decades and really. Are starting to pop up now and have a a, a really transformative effect, which is so cool to see.

[00:47:40] Anthony Alvernaz: Yeah. To that end, if, if we could round things out here, I, would love to know what's getting you excited right now. where are you finding, where are you drawing inspiration from? You know, whether it's what you're seeing in conversations, that, that proceed deciding to join a cap table or, or elsewhere in the world today.

[00:47:54] Anthony Alvernaz: what's most inspiring?

[00:47:57] Ajay Vashee: There is so much happening at the application layer in AI today that it's hard to give you a specific answer to that question. Honestly, like we invest very actively across the US and Europe. we invest across five different categories. As a fund, I spend most of my time on the application side.

[00:48:11] Ajay Vashee: We do application infra, consumer FinTech, digital health, and we're seeing really exciting opportunities across all five of those categories. we, the most recent investment that I made, that we announced was our investment in, in numeric. Before that we invested in a company called Pigment Ano another deal that I led, that's a company that's revolutionizing planning software and, kind of a parallel to what Numeric does for Accounting Pigment is doing for fp and a in many ways.

[00:48:35] Ajay Vashee: And, and so I spent a lot of time looking at companies across the office of the CFO software stack. but then there, there are categories now like that we all see like coding and customer support and search, whether it's consumer search or enterprise search that are being disrupted. in a really transformative way by ai, and so we look at a lot of those categories as well.

[00:48:53] Ajay Vashee: We've invested across many of those too, so everything we look at and see on a weekly basis now in this job is really exciting and really inspiring.

[00:49:03] Anthony Alvernaz: Amazing conversation today, Ajay. Really appreciate the time. For folks eager to connect further or follow your journey, generally learn more about you and IVP, what's, the best way for them to do that?

[00:49:12] Ajay Vashee: they can visit our, our website and we have many ways to reach out to the team over there. All of our contact information that is there as well. And if you're a, an aspiring founder or a founder, well on their way to building the next iconic company, we'd love to chat with you as well. So please reach out.

[00:49:27] Anthony Alvernaz: Fantastic. Thank you so much.

[00:49:29] Ajay Vashee: Thank you.

[00:49:30] Ajay Vashee: You've been listening to Incoming Statements, a production of Numeric. To learn how AI and automation are eliminating the manual burdens holding your accounting team back, visit numeric. io. Join us next time to hear from more top accounting voices on the challenges they're facing and where they see the industry heading.