Cherry is a financial technology company that helps medical providers treat more patients with a high-approval, cost-effective, and easy-to-use buy now pay later solution.

In this interview with Ryan Cannon, VP, Head of Risk at Cherry, we learn how he got into fintech, how he uses technology to scale his team, and what advice he would give to fintech leaders and operators navigating new challenges.

Hi, Ryan. You have a broad set of experiences in finance, ranging from business analysis to credit strategy, and at companies large and small. What was your journey into finance like?

Although it doesn't look so strange in the rearview now, I actually had an unconventional path into finance. I've always been interested in finance, and in stocks in particular—I remember reading books about Warren Buffett as a kid—but I didn't know how to enter the industry.

I went to the University of Virginia after attending Thomas Jefferson High School, and after school, I spent a couple years running restaurants, which was really fun. When I applied to graduate school, I didn't quite fit the typical candidate profile, but through a combination of luck and persistence, I was able to attend a program at Duke University.

Between graduating from the University of Virginia and attending grad school, Ryan spent a few years running restaurants
Between graduating from the University of Virginia and attending grad school, Ryan spent a few years running restaurants

And when I was there, I actually thought I'd go into equity research. By chance, I was able to meet some folks at Capital One through a case study competition we ran, since I was head of the finance club. I was really struck by how sharp and curious everyone I met from Capital One was, and how much they loved talking about data. Eventually, I decided to join Capital One as a Business Analyst.

How was that experience at Capital One? What did you learn?

It was an awesome company and had a great culture. But at the beginning, maybe for the first month and a half, I wasn't sure if the role was a good fit: SQL just wasn't gelling for me.

Luckily, I was able to learn from one of our Data Analysts, who took the time to spend many more hours than she needed to helping me get up to speed. And once that clicked, everything just took off.

Interestingly, my restaurant experience really helped out from a corporate standpoint because I had learned how to talk to strangers from all sort of backgrounds, which many recent graduates didn't know how to do as well. And I came out being this like gregarious, really chatty guy that also had the horsepower, and that helped me stand out.

Eventually, as I started to think about where I'd make the biggest impact, I realized that at a company with 30,000 employees, it would take longer to have a meaningful say in things. That's when I decided to join a smaller company.

At GreenSky, I worked in Credit Strategy, and at LendingUSA, I was Senior Director of Pricing, Credit Risk, and Merchant Risk. From there, I joined Cherry at around 10 employees. I've been here for 2 years and we're nearing 100 employees now.

From Day 1 until now, how has your role at Cherry evolved?

It has evolved so much.

Day 1 was just figuring out what we had. Cherry was so young that I didn't actually have a proper mental model of what it was going to look like. Even at LendingUSA, which was my company before, we had a hundred employees, so there were a lot of things that were already done before I had arrived.

The first thing I had to deal with was figuring out how we were performing. At the beginning, what matters the most is losses and delinquencies. I focused on vintage views and looked at loan statements over time—I wanted us to build the infrastructure that gave us the best view into how much money we were making or losing.

After setting up that infrastructure and doing some preliminary risk exercises, our founders came to me and said, "Hey, it's time to get a bank partnership." I hadn't ever done that before, but the company has a great attitude of, "Let's go figure this out."

That's crazy. How did you navigate that challenge?

I started by calling everybody I've ever worked with who knew about bank partnerships, and that led to a lot of introductions. I've found that in fintech, people are generally pretty willing to impart their wisdom.

Practically speaking, once we kicked off our search, we went through our selection process with a number of banks and just had conversations with them to see who would be the best partner.

And after partnering with a regulated banking institution, that meant there were a number of compliance requirements that we had to monitor. So my next job was to go hire a head of compliance—something else I had never done before. And then I helped build a merchant underwriting program. It's been about taking on one new challenge at a time.

With so much on your plate, how do you decide what to prioritize?

Weirdly, it's been kind of intuitive. One of the things I really appreciate at Cherry is there's a clear understanding of how much work somebody can accomplish at a given time. And I've found that our founders are pretty consistent in asking us to cut back on what we're trying to do—and do a few things really well—rather than trying to do too much. When you get stretched too thin, you just don't accomplish anything.

I've had seven or eight years of experience now in point-of-sale lending, and I tend to have a good sense of what might pop up or what the next step in our growth might be. I've scaled backwards—I went from a company with tens of thousands of employees, to a couple thousand, to one hundred, and then down to 10.

Once you know what your goal or destination is, a lot of it is just going out and meeting people until you find somebody who's been there already and is willing to talk to you. People are usually happy to talk because they know that, even with the roadmap, it takes a lot of work to get there. And once you've found the roadmap, it's just a matter of executing.

Cherry is pretty tech-forward. How do you think about using software to grow faster?

There are a million products out there that support fintechs now. It's important to choose the right ones, because they take away a lot of the operational challenges you need to solve.

Two examples of products we rely on are LoanPro (loan management software) and Finley (debt capital management software).

Finley helps us manage our debt capital. Right now, we manage one funding source. We're going to have more and more financing partners as we grow, and we don't want to have to hire full-time analysts just to do that. Instead, Finley comes in and we're happy to work with their team because they make managing all the day-to-day processes simple, and can help us scale.

On the loan management side, I've used LoanPro both here and at my last company, LendingUSA. The data is pretty accessible, and we've been able to construct all the data we needed, including data at the transaction level.

It's easier than ever to get a fintech business up and running now, just because many of the functions that you used to have to hire people for, you can now find external solutions to handle. For example, outside of Finance, we also use tools like Rippling and Carta to stay as lean as we can.

Have you ever worked on any projects that you were initially disappointed to be working on that ended up being surprisingly fun?

The thing that I was most disappointed by, that ended up being pretty good, was a rotation at Capital One.

After my first year there, I was promoted and was really excited about that, but after the promotion you do an automatic rotation. You don't really have any say in were you go. And when I got promoted, I did a rotation in the Collections Analytics department.

I didn't know much about collections, but I ended up working as an Evaluations Consultant. At the time, we were working on how to value the work of the collections department and setting up new programs. So I had to figure out how to evaluate collections performance. What I learned has actually stayed useful for my whole career. It's been an awesome value-add.

At GreenSky, my knowledge of collections helped me get really close with the operational leaders there and apply new technology solutions to improve what we were doing. It also helped me to work in credit, which was an area I wanted to focus on. So working in collections during that rotations program ended up being the best thing I could do for my career, but when I started it was something that I absolutely dreaded.

Awesome, that's a great story. Thanks for your time, Ryan!


Want to learn more?

Finley is debt capital management software that helps high-growth startups save time and money by automating routine credit facility management tasks. Today, Finley manages over $2 billion in debt capital for high-growth fintechs like Ramp, Parafin, and Arc. If you're interested in learning more about software that can help you streamline your debt capital raise and management, just request a demo or take a self-guided product tour of Finley. We'd love to chat!

All information presented herein is for informational purposes only, and Finley Technologies, Inc. does not assume any liability for reliance on the information provided. Before making any decisions that may affect your business, you should consult a qualified professional advisor.

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