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Building a Legitimate, Profitable FinTech Unicorn Using AI: Cynthia Chen, Founder of Kikoff (Part 2)

Posted on Tuesday, Jul 1st 2025

Sramana Mitra: Let’s come back to about 2012 when you have spent seven years in Deloitte in credit and consumer credit. What did you do next?

Cynthia Chen: Seven years later, I already had a child, and I didn’t want to travel as much anymore, so I returned to Capital One to work in the commercial and small business banking group for a little over a year. That was the time when companies in the FinTech space, like Lending Club were getting a lot of traction and media attention. So, I got curious.

A company called OnDeck reached out to me for the position of a Head of Risk Management, I decided to talk to them to learn more. Then I got very excited about the opportunity to help OnDeck make capital available to small business owners. I decided to leave Capital One and become the head of risk at OnDeck Capital. We took OnDeck Public in December 2014.

Sramana Mitra: How long did you stay at OnDeck?

Cynthia Chen: I was at OnDeck for almost three years.

Sramana Mitra: You’re finished with OnDeck around the 2015-2016 timeframe?

Cynthia Chen: Yes. In mid-2016, I left OnDeck and I relocated from New York to California for a new job as the Chief Risk Officer of a FinTech company called Kiavi.

Sramana Mitra: How long does that go on?

Cynthia Chen: That was a very important decision for me because my family was always living in New York City area. This move required that we relocate. I made the choice because I wanted to really join an earlier stage company. By the time I joined OnDeck, it was already Series D. I really wanted to see how an earlier stage company operated.

Kiavi was backed by top tier venture capital companies like Ribbit Capital and Foundation Capital. I decided to take the job so that I could see how a three old year old company would operate, just for more learning.

Sramana Mitra: Were you based in Silicon Valley at that point?

Cynthia Chen: Yes. I was based out of San Francisco.

Sramana Mitra: Was that also in small business credit?

Cynthia Chen: That was kind of small business. They provided financing to the contractors and investors who wanted to get bridge loans to finance a purchase of a house so that they could do renovation, construction, and then sell the house at a higher price.

Sramana Mitra: Flip it?

Cynthia Chen: Yes. It was to finance the investors who did house flipping. They were mostly small businesses that specialized in house flipping.

Sramana Mitra: Did that company succeed?

Cynthia Chen: That company is now doing very, very well. I think they’re profitable and they are now the largest bridge financing provider in the US. I think they’re doing pretty well. I think they did probably over $20 billion in loans cumulatively so far.

Sramana Mitra: When did you leave them?

Cynthia Chen: I left them in the summer of 2017. I took a break of almost six months working as a venture partner of Silicon Valley based venture capital fund, led a few investments for that fund.

I was also exploring what I wanted to do next. Do I want to become a VC or do I want to do another startup? Do I want to do something else? I took a break to do some investing and advisory work, and then I decided to join Mike Cagney, the former CEO and co-founder of SoFi in starting a FinTech company called Figure Technologies.

Sramana Mitra: What was that?

Cynthia Chen: Figure is a blockchain technology empowered Home Equity Lines of Credit (HELOC) originator. Figure is one of the top three HELOC originators in this country. And it provides very fast and fairly priced HELOC products to homeowners who like to leverage their home equity to get affordable financing so that they can consolidate that or finance a major purchase, et cetera.

This segment is part 2 in the series : Building a Legitimate, Profitable FinTech Unicorn Using AI: Cynthia Chen, Founder of Kikoff
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