From Dropbox To IVP: The CFO Turned VC Investor With Ajay Vashee

According to Ajay Vashee, former CFO of Dropbox and current investor with IVP, the most successful finance leaders are great storytellers.

During his four years as CFO of Dropbox, Ajay Vashee saw the tech company through many changes—scaling from 100 employees to 3,000, an IPO and the trials of the first years as a public company. Now, Vashee has transitioned to an investment role with IVP. One common thread, from opposite poles of the finance world: the power of a compelling story.

In this episode of Secrets of Rockstar CFOs, Vashee joins Jack McCullough to discuss the relationship between building companies and making strategic investment decisions. Listen by clicking below. The Q&A, lightly edited and trimmed for clarity, follows.

Listen to the podcast here

We got a great guest for this episode, so let’s rock. My guest is Ajay Vashee. Ajay is perhaps most famous for being the former CFO of a little company called Dropbox, perhaps you’ve heard of them, but now he’s presently a general partner at IVP. Ajay, welcome to the Secrets of Rockstar CFOs.

Thank you for having me.

We’ll get into it more deeply later. For those who might not be familiar with IVP, and I’ll admit I wasn’t until recently, what can you share about the group?

IVP is a 40-year-old venture firm headquartered in California with offices across Europe. We’re very active series B and series C investors. We’ve invested in companies like Dropbox where I was at and many other companies across the software and consumer universe.

I checked it out. It’s a very impressive portfolio you guys have brewing. Before we get into your career a little bit, where did you grow up?

I grew up on a small island outside of Seattle called Mercer Island.

I saw you put it on your LinkedIn profile. That made me curious. Are you from a big family?

I’m from an average family. I have a Mom and Dad, obviously growing up, and I have one younger brother, four years younger.

Is he in the tech business as well?

He works in climate change in the Bay area as well.

You must be proud of your baby brother then.


You had a great career and you spent a little time in banking, but I’d love to chat with you about Dropbox. Dropbox was your first CFO role, right?

Dropbox was my first CFO role. Dropbox was my first operating role because, as you said, I started my career at Morgan Stanley in banking. I then spent a few years at a different venture fund, a fund called NEA. It was while I was at NEA that we were doing some category work on file sync and share, the category that Dropbox operated and operates in. I fell in love with the company through that process and ended up joining, leaving the world of venture to step into an operating role for the first time.

You have to give yourself credit. For your first one, you picked a pretty darn good one. It couldn’t have worked out a whole lot better. You had a great eight-year run. You took them public as the company CFO. Is that correct?

That is correct. I joined in my initial role to help build and scale the finance organization at Dropbox and that was my first time doing that. We had a couple of folks on the accounting team and that was about it. It was a crash course in what a finance organization should be [and] an opportunity for me to go out and recruit talent across that org. It helped me get the learning curve on everything finance, and then I spent two years managing corporate development and M&A.

All of our acquisitions as a company and those two experiences prepared me to ultimately step into the CFO role at Dropbox, which I did about a year before we filedto go public and roughly a year and a half before our IPO. I was the CFO of Dropbox through the company’s IPO in the first 10 quarters, so two and a half years as a public company.

You mentioned building the team. A lot of people shared with me that the team to get you to the IPO sometimes does not have the same skillset and the same culture as the team after the IPO. How did you manage that a little bit to find people that would fit on both sides of the transaction?

That’s a great question, and it’s totally true. In that initial finance team that I hired or that initial organization that I helped to build, many of the leaders in that organization went off to join a company of series A and series B startups. They work through that journey again from product-market fit to $10 million, $20 million and $100 million in revenue. There was a different team that we brought in to help the company get ready for an IPO and ultimately navigate that transition from the private to the public markets and operate successfully as a public company. The team we had when we were a smaller startup running the finance organization was certainly different than the team we had as we got ready for that transition.

That makes sense. It’s probably true that the IPO choice is the holy grail for CFOs I suppose. It’s a transaction, but it’s also a cultural event. Dropbox and a lot of companies I’m sure are very passionate about an entrepreneurial, innovative type of culture. All of a sudden, you’re public and you have to behave a little bit differently. There’s pressure to make the quarterly numbers. What was that transition for you as the CFO of the company like?

It was certainly a transition. I think we were a very disclosive company internally to our employees. That was an important part of our culture and helped us achieve the scale and success that we did. We had to be more measured in how disclosive we were and which employees had access to what information as we transitioned to being a public company. There was a cultural adjustment associated with that.

In terms of our mission and our vision as a company and the energy we had as an organization executing towards that mission and vision, none of that changed. We were intentional about maintaining and keeping the company and the employees focused on the long term, on the next product, on our customers and on what was most important. We tried to mitigate the number of employees and people who had to focus on the short-term and the quarterly earning cycle. That earning cycle, as you alluded to, does take up a fair amount of time, and it is naturally more short-term in its orientation and focus.

Naturally, it’s going to change your department and the way you approach your job, but I suppose the magic is not to kill the great things that made the company IPO-worthy in the first place.

It’s interesting that you bring that up because I remember sitting in a meeting with one of the legendary crossover investors out there, the funds that would anchor your IPO and in many cases, invest in you as a private company to support your transition to the public markets. Think of funds like Fidelity, T. Rowe Price or Black Rock. These are active IPO investors. We were in a meeting with one of them before we went public. It was myself and our CEO, Drew Houston, who’s still CEO at Dropbox.

This investor asset says, “Drew, what are you most worried about in making this transition to the public markets? What are you most excited about?” I then got asked the same question. It had been hammered into me to avoid falling prey to the short-termism of the public markets. This is a common mistake that too many companies make. I had that top of mind and I responded to these questions and said, “The one thing I’m going to make sure we don’t do is fall prey to the short-termism of the public markets.”

And the gravity of that earning cycle, especially being a CFO and a newly public company is so powerful that even keeping that top of mind, I still remember when we went public—in our first quarter as a public company, we’d been giving guidance, but then there were all these shadow numbers and shadow metrics that people were whispering about and expecting us to hit and meet. All of a sudden you’re not only managing the company to the formal revenue guidance or the margin or profitability guidance that you’ve issued. You’re also juggling some of these shadow metrics and numbers. It became an exercise that involved too many people with too many resources. I think even knowing how big of a trap this can be for so many companies, we fell victim to it in our first couple of quarters as a public company.

It’s tough not to. You want to make the best impression you can on the markets right out of the gate. Your instinct in the principle is absolutely the correct one. It’s much easier said than done.

I would fully agree with that. There was a panel I hosted maybe to provide an interesting anecdote to that point. We had the head of FP&A from Netflix on this panel and we had two private companies. I asked this question, “How do you approach resourcing at your organizations between the current year and the long term, so the next 12 months and the next three to five years?” The two private companies had an answer of 90 percent this year because you have to hit your numbers and keep executing, you’re growing your business, and 10 percent long term.

Netflix’s response was 0 percent in the short term and 100 percent in the long term which felt like it was an exaggeration. That organization doesn’t issue guidance and they’re focused on building and creating revolutionary and new content that’ll come to fruition and launch in years. That’s how the incentive system internally is aligned. That’s almost a holy grail for people to get to from a capital allocation perspective. The more you can march up that spectrum over time, the more successful I’ve seen public companies be.

Zero to a hundred seems very hard to achieve from mere mortals I think. Other than that, any other insights you can share about what it’s like to be a public company CFO after a successful IPO?

For us, it was a very energizing and illuminating experience. It was a very clarifying experience. A lot of companies tend to dread the process of getting ready for an IPO and then going public and being a public company. We chose to take a more optimistic spin on everything and we wanted it to be this milestone moment for Dropbox in many ways. We wanted to lean into the best attributes of what it takes to operate successfully as a public company and make those an important part of our culture at Dropbox.

For us, the process of writing that S1, developing our roadshow presentation and crafting the roadshow video that every investor in your IPO is going to watch, we leveraged that as a moment to get tighter on our vision, strategy, roadmap and objectives. It was this galvanizing moment for the company working through the IPO process. We then try to make the storytelling aspect of the IPO an energizing process for all of us because you’re in so many meetings and on so many calls back to back telling the same story. If it’s a story that you truly deeply believe in and is exciting to you personally, then it comes off as genuine and authentic. We made sure to craft the narrative that way. Our CEO Drew and I could tell the story that way.

That IPO, as I’ve always heard, is quite a bonding experience between the CEO and the CFO. Maybe it goes the other way. Did your dynamic change during the IPO process? You’ve been living with each other pretty much for several weeks.

During the roadshow and then the first week as a public company, we’re spending a lot of time together. I think we had a lot of mutual trust and respect between the two of us, Drew and myself. I think you’re right. It was certainly strengthened through the IPO process. We focused on executing that as well as we could. I think that the positive momentum that it gave us made our relationship and the company even stronger.

It’s such a critical relationship, which doesn’t mean you have to go golfing on the weekends or anything. The mutual respect, support, strategic thinking and shared vision are critical things for companies these days. You can’t overstate that, particularly during an IPO.

You’re right and some of the pitfalls that I see companies fall into are if they lean too heavily in one direction, to your point on the partnership. The CEO is doing all the pitching and the CFO is talking about all the numbers, at these roadshow meetings, or after an earnings call and taking that burden on herself for himself. I’ve seen that be a pitfall where the CFO doesn’t build the right level of relationship with the buy side or the research channel lists that are covering the IPO as a public company. On the flip side, if the entirety of the burden is on the CFO’s shoulders and people don’t have a relationship or a sense for the founding story, the vision, the product roadmap and the CEO, then their level of conviction in your ability to keep delivering durable growth at scale is not there in the same way.

You developed what I’ll call a financial playbook in your time at Dropbox. I know it’s been proven invaluable and flexible and you’re still using it to a degree. I know you wanted to share a little bit about that and I hope that it can be useful to some other financial leaders. Tell us a little about that, and it better not just be a more efficient way to close the books.

Part of it is a more efficient way to close the books. We had a mission statement as a finance organization. It was important for us to develop this so we could engage and inspire everyone across the organization. That was a mission statement of continuous improvement and strategic disruption. We always wanted to be improving as an organization in everything that we did whether it was closing the books, how we manage the quarterly forecast or annual planning cycle, or how we supported our business partners across the company.

Headshot of Ajay Vashee with quote: "Optimize for a really analytical CFO who will also be a masterful recruiter and chief inspirational officer for your comapny."

That fell into the category of continuous improvement. Every year, we always wanted to ideate, launch and execute to completion one to two trajectory-changing projects. That impact orientation was important to us as well. It was continuing to strengthen the core and foundation that we built with continuous improvement, and then changing the trajectory of the company through strategic disruption.

I’ll give you two or three examples of what that meant for Dropbox, as related to continuous improvement. We set a goal in my final year as CFO to save 10,000 working hours through finance transformation and automation efforts. We leaned into a lot of emerging technology in RPA and the early innings of AI and the applications of AI to the finance tech stack and data, to free up analyst resourcing and time. People are spending more time on rote tasks like parsing through data, dashboarding and reporting, but they could spend more time on higher-value activities like understanding what that data means and what we should do about it.

We built a team around finance transformation automation that falls under the continuous improvement umbrella. On strategic disruption, as I mentioned, we were always on the lookout for different ways we could operate as a company to unlock our true potential. I’ll give you an example of two projects that we helped to ideate and work on for Dropbox. One was as a private company and one was as a public company. As a private company, we were close partners to our infrastructure organization. What many people don’t know about Dropbox because they engage with the product with the application layer is there’s an enormous back end and infrastructure footprint to what Dropbox does to store and serve all of the billions and billions of files for its users globally.

I can imagine. I use it every day. I can’t recall it ever being down when I’ve used it. I’m sure it’s down once in a while because everyone is, but it’s a remarkable achievement. Anyway, sorry, I started interrupting, Ajay.

No, of course, it’s a great point. For us, reliability and and uptime are important service factors. For the longest time, we had built and scaled the company on the back of Amazon web services. Dropbox wouldn’t have gotten to the scale it did and it wouldn’t be the company it is today had it not been for the availability of tooling like AWS and the public cloud to get up to speed and scale very quickly. At a certain point in time, our strategic finance organization and dialogue with our infrastructure team began to realize that there could be a pretty compelling opportunity for us to migrate off of the public cloud onto our own internal custom-built infrastructure.

It was going to be a big and bold bet, but it was one that we felt would allow us to increase our gross margins pretty meaningfully. It was one that would allow us to improve performance to your point on service and reliability globally. There were certain regions in the world where we had poor buffering speed for a video that you sort on Dropbox and other regions where it worked fine. We wanted to control that ourselves by owning our own infrastructure.

From a strategic perspective, at our core, we were this company storing the world’s data and the world’s most important content. We wanted to own that data and content ourselves and not be reliant on a third party that might compete with us to do that. We had these three rationales that we outlined and we ultimately decided to engage in this buildout. It was a $400 million capital investment as a private company, which raised eyebrows among our investors going, “Why are you spending all this money when you can be leasing this capacity from Amazon?”

Ultimately, it allowed us to double our gross margins from roughly 40 percent to 80 percent by owning that hardware and software stock ourselves. That margin expansion opened up the IPO opportunity for Dropbox and gave us true software gross margins and a profile that would be attractive in the public markets. That was an important project we helped to spearhead within the finance organization as a private company.

As a public company, the last example I’ll share, we launched a project called Project Diamond. It was an effort to map every dollar spent as a company and assign an ROI to that spend. That could be performance marketing spend to acquire new business users, which traditionally has been more straightforward to manage and measure. There are some established practices and tooling out there to measure the ROI and return on that spend. It could also be spent on legal contracts every year, or team building an off-site spend or the spend on your kitchen expenses to feed employees.

We try to quantify and assign an ROI to all of this and it opened up some interesting opportunities for us to pull back on spend without sacrificing our long-term growth aspirations or potential. That was a project that allowed us to cross the formal threshold of profitability as a public company. Whether it was doubling gross margins or crossing that threshold of profitability, we were always on the lookout every year. We wanted to launch one of these projects that would fundamentally change the shape of the business at Dropbox.

You came from investment banking. The most common path to becoming a CFO is through public accounting. I know you’ve always shared that your team is instrumental in doing this. Did you have a nice blend of people from public accounting who brought that skillset and that mindset to the project or are they people like you who are strategic finance getting involved in these things?

Each one of these projects was a total team effort. My team was pretty diverse in terms of their background. In my team of direct reports, I had a chief accounting officer who had worked through IPOs in an accounting leadership role successively two or three times before we hired him. He understood that process inside out. I had a VP of FP&A who had led FP&A at a very successful public software company through their IPO, 10 years of being raised as a public company and then ultimately it sale to Oracle. And then a VP of corporate finance and strategy who was a veteran managing director in the technology investment banking group of Goldman Sachs.

He led the IPO process from the other side of the table 50 or 60 times before we hired him and brought him to Dropbox. I had a great treasurer, a head of tax and an incredible chief of staff. It was that group of direct reports that allowed us to achieve the success we did, whether it was on these products as a private or public company or the IPO process itself.

My understanding is a lot of your former colleagues at Dropbox, alumni if you will, are still using some of the methodologies that your team developed when you were there. Is that fair to say?

I think we created a culture in the organization that certainly people have brought into the companies that they’ve transitioned into over time. One of the rockstars on my team took over as a CFO when I transitioned out to join IVP. I know a lot of that same philosophy is still being embraced there or in other organizations.

We had some of the stars on our strategic finance team go off to join OpenAI in senior roles. The chief operating officer and the VP of finance at OpenAI both began their operating careers at Dropbox in the strategic finance organization. A lot of that same philosophy and culture is present there as well. The CFO at Figma started on that team as well, and the CFO at Plaid. There are a number of leading companies in Silicon Valley that got their leadership teams and their finance roots began in that strategic finance organization at Dropbox.

The tool now, I’m assuming you must share that with the portfolio companies that you’re involved with.

Totally. That’s an important part of my job today. I spend a lot of time in active dialogue and mentorship with our portfolio companies’ CFOs. Both the CFOs of companies I’ve helped to lead investments in, but more broadly CFOs across our portfolio, as they get closer and closer to a potential IPO, we’ve ramped up that dialogue in the relationship. That’s one way. We launched a community at IVP shortly after I joined called the IVP CFO Collective. It’s the first community of its kind for growth state CFOs.

We bring all of our portfolio companies’ CFOs, as well as other CFOs in the broader tech ecosystem, together pretty regularly for events that we try to make focused, curated and relevant to the problems and challenges they are facing on a day-to-day basis. A few examples. We hosted a pricing strategy workshop. The team at Simon Kutcher and Partners came in, which is the leading pricing strategy consulting firm out there, to do an interactive multi-hour workshop with every one of our portfolio companies to identify what was working and what was broken about their current approach to pricing. That was useful to many of them.

We hosted, in the wake of the [Silicon Valley Bank] crisis a few working sessions with our portfolio on everything that we were hearing and mitigating action to take. We host an annual State of the Market dinner to walk CFOs through everything we’re seeing in the market, which key metrics are most important today, and how these companies benchmark against the median deal at the 75th percentile and the 90th percentile, so they can get a sense of how that next fundraising might go or how they might be received when they ultimately go public. We host that annual dinner. That’s important as well. I try to stay very actively engaged and plugged into that community today.

You made the transition from being a CFO to joining IVP. What attracted you to not only IVP but a different career path altogether?

I had briefly worked in venture before my time at Dropbox. I was a younger associate in venture looking around the table. I noticed that a lot of the best investors that I was working with at the firm I was at, and co-investing with across the world of venture, were folks who had helped to build and scale enduring iconic companies themselves. They had real meaningful operating experience and they leaned on that experience.

I felt like if I wanted to build a longer-term career in venture, which I do love and enjoy, stepping into an operating role at Dropbox would be the best thing I could do for my career and it’s been so true. I always had in the back of my mind this intention and thought that I might return to the role of investing. If I was going to make a return, I wanted to return to a fund that was in the Dropbox family. IVP was our series B investor at Dropbox. I got to partner with the firm very closely as an operator for almost 10 years.

They were an incredible partner to us. I wanted to join a firm that had a growth focus on serious B+ because my time and my journey at Dropbox was our scale-up from 100 to 3, 000 employees, from $45 million or $50 million in revenue to nearly $2 billion in AR, and then private to public as we’ve talked about. It was that quintessential growth journey. That is the journey that we help companies on here at IVP. It was a combination of knowing the firm well and its focus on growth. It’s been an incredible place.

Your firm is a growth investment? Any particular philosophies you have in making your investments?

Headshot of Jack McCullough with quote: "As a CFO, you have to be analytical but it's about the people more than anything."

Most importantly, a very active partner to the companies that we invest in. Back when I was an operator at Dropbox, IVP helped to place our first lead independent director. That was Condoleezza Rice, the former U.S. Secretary of State. She was an incredible force of nature that helped shape the company in many ways. They were super active partners. She started off as the first independent director we had at Dropbox. And then she quickly became the lead independent director for our IPO as a public company.

She was helping to run and manage the board of directors at Dropbox and many parts of the company and partnership with our CEO. In any case, they helped to place her and then the IPO process itself, we’re so active with companies in their process. We’ve helped nearly 140 companies through that process in our history. There is a lot of institutional knowledge that we have that we lean on. As a former CFO joining the ranks here who’s been in that process recently, we’re hands-on in a way that many firms can’t be.

How many active investments do you have right now roughly?

As a firm, we have about 80 portfolio companies. The majority of those are private and roughly 15 to 20 at any point in time will be public investments where companies have gone public and we still have a stake. Then personally, I’ve helped the firm with 5 or 6 investments since joining three years ago.

What is your role when you’re on the board of these companies?

In the majority of companies that we invest in, we’ll take a board seat or board observer seat. I’m on the board of most of the companies that I’ve helped us invest in.

I’m assuming you’re a wonderful mentor to the CFOs of those companies.

I spend a lot of time with the CFOs. I was on a Zoom with one of our portfolio companies’ CFOs talking about both IPO readiness and investor targeting heading into that potential deal for them. I do spend a lot of time with our CFOs. I also have to make a concerted effort to spend a greater amount of time with our CEOs because, naturally, I gravitate towards what I know best. That’s been a new muscle for me to build but it’s been a learning experience and a ton of fun.

At this point in my career, it was still relatively rare for a CFO to get a venture capital type of role other than to be the CFO of the fund perhaps, but not in the world you’re doing. Is that something more common than I realize? Is it maybe a trend in the future for CFOs to become VCs and PE-type investors?

It’s a good question. It’s not all that common today. I think historically there were a few different career paths to making it to the the partner level at venture capital funds. The most common career path is starting off as a younger analyst or associate, and then building the right level of domain knowledge and a track record, and then eventually making it to the partner level. After that go-to-market, sales leaders and product leaders have occasionally taken a career path from an operating role into an investing role.

I think that with the rise of strategic finance talent in finance organizations across the tech ecosystem and more and more folks graduating from those roles into the CFO role, you have this rise of these strategic CFOs. I wouldn’t be surprised if you saw more folks over the next five to 10 years transitioning from those public companies’ CFO roles of an organization they’ve helped take public into a venture investing role.

I think you gave me the title of my next blog, The Rise of The Strategic CFO. You’re right, though, because more and more CFOs are becoming CEOs. Certainly, for a while, they’ve been getting seats on boards. A lot of times, it was to be on the audit committee because they needed a financial expert, but now they’re getting seats for their overall business acumen, not just their financial expertise. It seems like the next great thing that they’d be active investors, too. I wanted to change gears a little bit. You’re a busy investor. You’re on six boards, and I understand you travel quite a bit.

I do. We opened up a London office here at IVP. A lot of the interesting deals that we see are in the U.S., but also more and more so in Europe. Our focus is between those two geographies, so I spend a fair amount of time primarily in France and Germany.

Where are you now if I may ask?

I’m in San Francisco in my office here with my DBX neon logo behind me.

Maybe it’s too bad that this is an audio experience for most because he’s got this terrific-looking Dropbox logo right behind him. You’re a lifer it seems right. You have a lot going on in your life, not the least of which is you have two daughters as well. How do you juggle all of your responsibilities in life?

It is certainly a team effort both at work and at home. At work, we have a phenomenal team here at IVP both in the U.S. and Europe. We work super closely together and we’re always there for one another and that helps when one of us has an obligation whether it be personally or at home; there’s always someone to step up behind you. At home, it is certainly a family effort. My wife is the chief marketing officer at one of our portfolio companies, believe it or not. She leads an equally if not more busy life than I do, but we are very lucky in that my parents and my wife’s parents have both relocated to live near us with their grandchildren. We have backup support whenever we need it, which has been a lifesaver countless times.

Your wife doesn’t happen to be VP of marketing at a company where you’re on the board. Is she?

She is the chief marketing officer at one of my portfolio companies which happened coincidentally, but I’m not on the board of the company, which is good. Otherwise, that would that would be a tricky situation. She’s the CMO at a company called Figma.

You could heckle her at board meetings when she’s making presentations.

I would love that, but she would not.

I’m not sure that’s a good long-term strategy. How old are your daughters, Ajay?

Our daughters are 7 and 4.

Real fun age. They are still into Daddy and always will be, presumably.

That’s the hope, although I’ve heard many interesting war stories from parents of teens. I’m keeping my fingers crossed.

Mine are 21 and 19. They have no use for the old man. I have two boys, so it’s a different dynamic. Do you have any interesting hobbies or other things in your life that keep you busy as well?

I do like to run to stay fit. We live in a pretty hilly part of the Bay Area. That’s been a fun hobby that I’ve cultivated over the past couple of years. We are investors in a company called Whoop. I’m not sure if you’ve heard of them, but they’re the leading fitness tracker out there.

They’re in Boston, aren’t they?

They are headquartered in Boston. A lot of the pro athletes and pro leagues will use Whoop. Whoop helped me get into hill running, which has been a ton of fun and a great cardio workout. That’s something I spend a lot of time doing. And then I love building Legos with the daughters. We’re always on the hunt for a new Lego set. We have a couple that are full of these fun projects that we’ve built together. Those two things keep me busy and then traveling for sure.

One of the companies that I’m an investor in is in Germany. It’s a company called DeepL, an AI-powered language translation platform. It’s gotten me more and more into the path of language learning. Given how much time I spent in other countries like France and Germany, I’ve started to try to learn the native languages there. Although I’m very much a novice, so you can’t ask me anything on this episode today.

I had six questions, but I’m going to be nice and not put you on the spot. I’d like to close this with if you could give some advice to the next generation of CFOs, maybe those controllers and VPs of finance or even maybe a first-time CFO, what should they be focusing on to achieve success in their career paths?

It’s a good question. Maybe the approach I’ll take here is not advice for those up-and-coming CFOs or VPS of finance but more advice for CEOs. When you’re hiring for that CFO or you’re deciding whether it makes sense to promote someone within your organization, that’s a conversation I’m in a lot with our portfolio companies at IVP. My advice is to optimize for an analytical CFO who will also be a masterful recruiter and a chief inspirational officer for your company.

Finding someone smart is table stakes. Make sure you do that and evaluate people the right way for that component of the role. What most people underestimate is that a CFO’s most important job is to build a world-class team. What almost every CEO doesn’t understand is how much your CFO is going to be a spokesperson for the company internally and externally, especially when you go public. You have to hire someone who is able to craft themselves with their team, and craft and deliver your company narrative better than anyone else, including you. Better than you as CEO of the company.

Communication is so important and it can make a difference. If you can tell a very compelling narrative and help investors build conviction that you’re going to grow at 30 percent, 40 percent, or 50 percent a year for the next 10 years in an incredible way, then you can trade it in multiples that are two, three, four times higher. You’re going to be valued even more as a public company. Most people get that part of the job wrong and will opt for this person who has been there and done that. They might have come out of the big four. They might have been CFO twice before but they don’t optimize for that emerging and rising talent that’s going to inspire people inside the company and out.

It’s interesting because I interviewed a lot of people who weren’t CFOs, but they work with CFOs. CFOs often work for investors and CEOs. What makes a great CFO, it was very rare that anyone would mention technical skills. I came up with an acronym for it. It was TRICE, Transparency, Resiliency, Inspiration, Collaboration and Empathy. Several years ago, if I said that’s what you look for in a world-class CFO, people would hit me or at least rise at me. I’m from Boston. It is remarkable. It builds upon what you’re saying that it’s a people job. You have to be analytical, but it’s about the people more than anything.

People and communication, I would agree with you. Maybe the last fun fact for you, our founder at Dropbox is also from Boston. Not sure if you know that. He’s from a town called Acton.

I live ten minutes from Acton.

He got to swing by on the roadshow and he insisted every morning when we were in Boston for that leg of our roadshow that we stopped at Dunkin Donuts to get our morning fuel.

A true Bostonian. The Boston Red Sox and Dunkin’ Donuts are the state religions around there. It’s not funny but if you go to parts of Massachusetts and you ask people how to get to Starbucks, people are going to send you to a Dunkin’ Donuts.

Willfulness in action. I like it.

It’s not mean-spirited but why do you want to go to Starbucks if you know what I mean? Go to Dunkin. You’re in Massachusetts. This has been great. I know you’re busy. I do want to thank you for your time. I want to give you the last word. Any final thoughts you’d like to share?

This was great. I’m excited to be here and on the episode with you and I’m probably most excited about the next generation of rising talents in finance. We have so many incredible analytical rising stars out there. If you’re running the finance or organization at an exciting tech company out there, we invite you to join the IVP CFO Collective and be part of that community.

Fantastic. Thanks, Ajay.