Life at Reggora

Meet the Team: Kevin Flynn

Welcome to Reggora’s “Meet the Team” series! Reggora is powered by a team of smart, hard working people dedicated to the mission of appraisal innovation, and we’ve all taken very different paths to get here. In this series, we’ll introduce you to different members of the Reggora family. This week features Kevin Flynn, who joined the Reggora team in January 2020 to lead the Product team and align product strategy across departments.

Kevin Flynn: Vice President of Product

Image of Reggora VP of Product Kevin Flynn for the "Meet the Team" series

Q: Tell us about yourself. Where did you grow up? Go to school? What do you enjoy doing?

A: I grew up in Concord, MA and after living in Boston for 10 years, now live in Belmont, MA with my wife, Lauren and two amazing kids, Olivia and Declan. I graduated from Williams College with a degree in Economics. Some of my all-time favorite things to do are to spend time with my family, entrepreneurship, and flying/aviation (both of which were embedded in me through deep family history!)

Q: Where did you work before Reggora?

A: After spending my first 3 years out of college in investment banking at JPMorgan, I started my first small business called CommunityRoot in 2012. We built a B2B SaaS product for managing early childhood education programs, and it is currently servicing hundreds of thousands of registrations per year. In 2015, I started my first venture-backed business - a startup called Fam. We built an interactive video consumer product that scaled to millions of users before being acquired by DraftKings in 2018. As part of the acquisition, I spent the next year and half leading the Daily Fantasy Sports Games team and founded the first Activation product team within DraftKings. 

Q: Why did you join the Reggora team?

A: The list is long! I have a background in finance and a passion for real estate, and the real estate/fintech space is one I’ve wanted to get into for a while. When I first met our co-founders, Brian and Will in 2017, I was really excited about what they were doing and their passion for building. After reacquainting with them in 2019 and hearing the journey they had been on and the vision for literally transforming valuation for residential real estate - the largest asset class in the world - it became a no brainer to join.

Q: What do you do here at Reggora?

A: As Vice President of Product, I’m responsible for making sure we’re shipping the best possible  product for our customers and our business. Feedback and empathy for users is the center of how our product team makes decisions, ensuring we’re delivering value and delivering on our promise to the customer. We use this feedback coupled with data to build a strategic product roadmap that gets us closer to our vision of two-day appraisals. As a team, we aim to always raise the bar and push the envelope in terms of innovation and constant attention to detail. My main focus in this capacity is to ensure my team has what they need to be successful while also coordinating with the other departments to help align on our product strategy and competitive positioning. 

Q: What’s something that’s surprised you since joining the team?

A: I think the overall readiness for the market is like nothing I’ve ever seen before. Mortgage represents the largest transaction most individuals will ever make, yet as an industry, it has largely been ignored by the tech startup world. 

Q: How have you handled the switch to remote work?

A: It definitely comes with pros and cons. Like most of us, I miss the in-person human interactions. That’s tough to replace. That being said, as a company we haven’t skipped a beat, which I think is a testament to each person at Reggora.

Kevin, our product certainly would not be where it is today without your hard work and dedication. Thank you for sharing your story with us, and for all that you do here at Reggora.

We’re continuing to hire across all departments here at Reggora. To learn about joining the team and see our open roles, visit

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Meet the Team: Kevin Flynn