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I sat down with Chen Amit, CEO and Founder of Tipalti, a global fintech platform that processes billions in payments globally and has achieved a remarkable 99% gross revenue retention rate by focusing on an often-overlooked segment: companies with 100 to 1,000 employees.
With licenses across 50+ jurisdictions and a clear path to capturing significant market share of what Chen describes as a $100 billion opportunity, Tipalti is very well positioned to continue growing fast. In this conversation, Chen shares insights on everything from the art of saying no to customers to building moats that AI can't replicate.
Q&A With Chen Amit
The following is a summarized transcript of the podcast
Miguel Armaza: You've talked about the importance of intense focus in building Tipalti. How did you apply that principle in the early days when you weren't even sure if this was a real company or just a project?
Chen Amit: It's both about intense focus and having your center—your backbone and belief system. Understanding the problem, the solution, and the customer is critical because, in many ways, the customer is not the one to ideate or conceive new solutions. It's up to the entrepreneur to come up with the ideas and find the right fit.
I had two first customers: InfoLinks and Play Media. Through working with both of them, I figured out what the challenges were and how to serve those challenges. For example, how do you make a global compliance challenge accessible to a small company CFO who has no direct reports? The finance department was literally just them.
When I presented my technical approach to the head of engineering at InfoLinks, he didn't like it. He thought it wasn't sexy enough, wasn't exciting enough, and tried to push me toward a different approach. But I knew that if I followed his advice, it would make it much harder for my customer—the CFO. So I actually rejected his request. I had two customers, and I was turning down my first customer's technical leader. The only way to do that is if you have a very strong belief in the problem, the solution, and how you deliver value.
Miguel Armaza: That's fascinating—it's not always about following the data, because you could argue the customer was telling you this wouldn't work. How do you balance data with intuition?
Chen Amit: You can argue that the interviews and shadowing of the CFO represent data. But they didn't tell me "do this or do that" because they don't know how to tell me—they're finance people. It's not their place to tell me which technology to implement.
These were two different data points. One had an emotional challenge because you're facing someone directly, and you need to remove the emotional aspect and just look at the data. The engineering leader was focused on being a geek—and I'm also a geek—but when you geek around, you like shiny new objects. You don't want to go back to whatever you used two years ago.
I was looking to optimize for ability to sell and ability to serve while minimizing user friction. Whatever a finance person needs from technology to serve them well—that was my focus.
Miguel Armaza: Speaking of saying no, how do you handle the really difficult NOs as a CEO?
Chen Amit: I think it's part of my DNA. There are personality profiling systems like the Enneagram, and I'm a Type Eight. Type Eights care less about what others think about them and more about protecting the family. I listen and care about what you say, but I have the ability to distance myself from the hard emotional aspect of saying no and just focus on the data.
In my past life, I had a similar situation where I was a junior leader who had just come out of business school. I came up with a product idea that the CTO of a 1,000-person organization—someone everyone bowed to—said we should be very careful about because no one does it that way. But all the analysis my colleague and I did showed very clearly that we should go with our approach. Eventually, we won with that. I'm very analytical and data-oriented, always trying to do what's best for the company while keeping egos and emotions in their proper place.
Miguel Armaza: Let's talk about your customer evolution. Can you share how the type of customer you work with has changed from the early days to now?
Chen Amit: I started with two ad tech companies, then looked for more ad tech, crowdsourcing, and gig economy companies. We evolved from that digital mass-pay segment, but my head of product and I started thinking about how this was just a fraction of the global economy—single-digit percentage points.
Then one of our customers reached out and said, "I pay thousands of publishers with you, and it takes me 15 minutes. Then I pay 100 bills for laptops, rent, and food, and that takes me half a day. Can you apply your magic to those non-publisher payments?" We said absolutely, because it was already something we were planning.
That's when we started going into traditional accounts payable about 11-12 years ago. When I hired Rob, our president, who came from NetSuite, he looked at our customer base and said, "Oh yeah, it's mid-market." That was the first time I understood who we were serving.
Miguel Armaza: What makes the mid-market segment so unique and challenging?
Chen Amit: Mid-market for us means companies between 100 and 1,000 employees. It's a very interesting and challenging market. Small business is easier to serve—companies like Stripe enable card-first, interchange-first products that make for easier entry. Enterprise is complex, but you have lots of resources, large deals, and time to bring in integrators.
When you think about a 200-500 person company, resources don't go toward finance—they go toward building the product, the brand, serving customers. Back office is an afterthought. But the level of complexity is already increasing. You may have subsidiaries in other countries, employees or suppliers globally, accountants, auditors, more complex approval workflows.
You have increasing business complexity but limited ability to execute—very small teams, very few resources. You need a product that solves many problem domains because that customer can't buy a dozen discrete products and integrate them. So you need breadth and depth and simplicity—these are the three legs of our product strategy.
Miguel Armaza: How have your customers' needs and expectations changed over the past decade?
Chen Amit: The biggest change has been market education. The pains were always there, but the comment we used to get was, "Wow, I didn't know that was possible. I didn't know you could go from invoice to payment and abstract all those complexities."
Now customers are more comfortable asking us to do more for them, and they expect us to be the one delivering that value. Before we add new functionality, we interview customers and ask, "Is this something you need? Is this something Tipalti should serve you with?" They say very much so. They don't want to go and add another solution.
We just did research on keywords like "accounts payable" and "accounts payable automation"—we're seeing very strong uplift in demand. Our brand and reputation are taking off. The market is still very green field with very small penetration, but there's much greater understanding of the availability of solutions.
Miguel Armaza: With AI disrupting software development, how do you think about competition from AI-first startups that can build quickly?
Chen Amit: When I thought about AI's disruption of the software industry, I realized that what used to take a long time, now there's talk about the first one-person unicorn—someone who will build a unicorn almost alone. A friend is doing exactly that with his company.
Someone can come up and build something new and fancy very quickly. But what they cannot do is build the license portfolio that we have. We have licenses in 50 states in the US, plus UK, EU, and Canada. Each license takes 6-18 months. Many take 18 months. Each bank integration takes 12 months if you need the level of integration we need.
We have huge amounts of data from our customers, fund flow data, and reputation and trust that no LLM can replace. At the same time, if a disruptor comes, we need to be able to fend off disruption just as fast. If we're organized correctly, we can build in two months what a disruptor built in two months, while having all those assets they can't replicate: trust, licenses, data volume, payment volume, bank integrations.
Miguel Armaza: You've mentioned that "once-in-a-decade" events now happen every six months. How has this changed your approach to leadership?
Chen Amit: For better or worse, for the last five years, company leaders have been trained in once-in-a-decade events every six months. Since COVID, we've experienced what used to be once-in-a-decade disruptions constantly—economy pressures, recovery, bank collapses, financial stress, wars around the world.
It makes you more immune to drama. First, you don't do knee-jerk reactions. You wait, you pause, you don't do anything aggressive until you fully understand the situation or until the dust settles. You have to prepare for constant change. Sometimes you need to zig and zag—it's not always "pause and think." When the data shows you need to make changes, you have to be brave.
Have an agile mentality, a flexible mentality. Don't worry about the rules of the game changing. If they change, change with them. Don't play yesterday's game—play today's game, and tomorrow it might change again. You have to have a center and vision, but the rules at the edges might change.
Miguel Armaza: Looking at the IPO market, there seems to be plenty of investor interest but hesitation from tech companies. What's your take on going public?
Chen Amit: There's a lot of dry powder looking for IPOs in the investment world—tons of it. When banks survey investors, the hunger for IPOs is higher every month. There's no lack of interest from the investment community. What's missing is interest from the tech company community to go public.
Some of it is post-trauma from the 2020-2021 IPO and SPAC period where many went public and it wasn't a great ride—neither personally for founders nor for companies. The stock goes up and down, and all the pressures hidden in private companies become visible.
I see a lot of hesitation from founders, especially companies that invest in growth where there are still changes and uncertainty in revenue streams, making forecasting hard. For us, we'll go public when we're ready. IPOs are going out at around $600 million to $1 billion range right now. We're not there yet, and we still need to build some internal capabilities. It's probably a couple of years before we can go public.
Miguel Armaza: What's your long-term vision for Tipalti and the market opportunity you're addressing?
Chen Amit: Our North Star is focusing on the mid-market, being the best at serving finance leaders in companies with 100-1,000 employees, and being the de facto go-to for everything mid-market finance—and maybe beyond finance at some point.
There are about a million mid-market prospects worldwide. With our licenses, we can serve two-thirds of them—North American and European markets are addressable for us. The million companies represent roughly $100 billion per year opportunity. We're the market leader with 1% gross annual dollar churn and 99% gross annual dollar retention—second to none.
The market is significantly underserved. We're at maybe 6-7% penetration—it's mostly greenfield. Most deals we compete on are non-competitive: it's us versus status quo, versus the customer changing how they do business. If we maintain our leadership and end up with 10-20% of the market, we'll be a $10-20 billion revenue company. So we will do very well.
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