About Huckleberry

Huckleberry offers simple, fast business insurance—powered by technology. 100% online. 100% easy.


At Huckleberry, we're on a mission to make insurance work for small businesses. Over the past decade, technology has changed the way we run companies—from accounting and tax prep to customer management and payment processing. But small business owners are still forced to buy workers' comp, general liability, and property insurance via an offline process that can take weeks to complete.

We want to change that by providing business insurance products that are simple, fast, and 100% online.


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    Bryan is co-founder and CEO at Huckleberry. His career has spanned insurance and tech—in fact, he started out in the actuarial department of Canada Life before joining a San Francisco-based venture capital fund where he invested in technology startups.

    Bryan holds a degree in Actuarial Science from University College Dublin and an MBA from Harvard Business School. In his free time, he can be found testing the limits of his health insurance on a pair of skis or watching Liverpool (finally) win after a lifetime of hurt.

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    Bill joined Huckleberry as CTO in March 2021 to lead Huckleberry’s product and engineering organizations. Before joining Huckleberry, he was VP of Engineering at Root Insurance, where he built out new product lines for renters and homeowners insurance, and led the engineering department through 4x growth and an October 2020 IPO. Bill previously spent seven and a half years at Amazon as GM of the Amazon Pittsburgh corporate office and GM of the Translation Services and Products organization.

    A proud husband and father of two boys, Bill is passionate about mentoring other technologists. He currently mentors multiple CTOs across the globe. In his free time when he is not immersing himself in technology, he loves camping, bike riding, and tackling large home improvement projects.

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    Braden joined Huckleberry in September 2020. Before joining Huckleberry, Braden was Chief Insurance Officer and the first employee at Jetty, where he built out the full scope of insurance activities, including product and portfolio strategy, carrier/capacity relations, underwriting, policy administration, and claims oversight. Previous professional experiences include membership on the Executive Management Board, several leadership roles at QBE North America, and McKinsey & Company, where Braden engaged with leading companies in the financial services industry, focusing on property & casualty insurance.

    Braden received his MBA from the UC Berkeley Haas School of Business. Some might say he’s talented at karaoke.

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    Jason joined Huckleberry in April 2021 from Root Insurance. Jason has a unique blend of finance, strategy, analytics and engineering skills, and specializes in unit economic and growth strategies. Jason was one of five key contributors to Root's IPO in 2020. Prior to Root, Jason spent 10 years at SaaS & B2B businesses based in Columbus, Ohio, growing businesses from concept to eight-digit revenue and contributing to several acquisitions.

    Jason spends his free time outdoors with his family of five, provides CFO/CIO services to small minority-owned businesses, and holds the Delaware, Ohio third-grade frisbee toss record.

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    Stephanie joined Huckleberry in July 2021. Prior to joining Huckleberry, Stephanie was at Candid, where she built out the sales function from 8 to 50+ people. At Candid, Stephanie developed the sales process, tools, training, and metrics and was a key driver to Candid’s revenue growth. Before Candid, Stephanie worked at IGS Energy, where she led the transition of all third-party sales into a new in-house sales organization.

    Stephanie spends her free time camping (read: glamping) and boating. She loves cooking and recently managed to "master" the art of making sushi.

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    Tom joined Huckleberry in August 2020. Before that, Tom built and scaled the marketing function at multiple hyper-growth companies, including Zendesk, Intercom, and Toast. Tom has extensive experience building marketing programs from scratch to tap into new industries, buyers, and global markets, and focuses on balancing brand and performance marketing initiatives.

    After an extended pitstop in San Francisco, Tom is back in his native New England and is based in Boston, MA. Tom received his BA from Middlebury College and is fluent in Spanish and Japanese. He is a connoisseur of apple cider donuts.

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    Antony joined Huckleberry in January 2020. Before joining Huckleberry, Antony was a leader in the e-sports and professional gaming world. Antony worked at Tencent and Riot Games for their number-one global titles in the mobile and PC genres, respectively. He oversaw the successful execution of hundreds of events in over 15 countries, garnering audiences of over 50,000 in-person viewers and hundreds of millions of online viewers.

    Antony loves traveling and exploring nature in his spare time through hiking, scuba diving, bike riding, and camping.

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    Amy joined Huckleberry in April 2021. Prior to that, Amy was at Root Insurance as the second member of its People Team and eventually became Director of Recruiting, helping to scale the organization from around 50 employees to over 1,300 during her three-and-a-half-year tenure. Before her time at Root, Amy taught yoga in several studios around Columbus, Ohio, and was in an IT Project Management rotational program at Cardinal Health.

    Amy received a business degree from the University of Michigan, making her a Wolverine living in Buckeye territory. (However, she’s willing to root for OSU if they’re not playing UMich.)

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    David joined Huckleberry in January 2021. David was previously an investor focused on financial and technology companies. Before investing, David was a consultant at McKinsey & Company, focusing on the insurance vertical in their Boston office. David currently lives in the Bay Area but grew up in Mexico City and has spent time in Boston and New York.

    David has a B.Eng. in Chemical Engineering from MIT. His favorite pastimes include hitting the East Bay mountain bike trails, attempting to kitesurf, and taking his wife and dog, Waffles, on exploratory hikes. David is not terribly sure about mustard.


We're a team of digital natives with deep insurance expertise, backed by some of the world's most notable investors.

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