VP of Engineering, Root Insurance Company
GM – Translation Services and Products, Amazon


Small business owners have enough challenges on their plate. Figuring out how to acquire the insurance they need to protect their employees and their investment should not be one of those challenges. Huckleberry wants to change that by providing business insurance products that are simple, fast, and affordable 100% online.

Huckleberry is backed by Tribe Capital, Uncork Capital, Crosslink Capital, e.Ventures, Postmates CEO Bastian Lehman, Apartment List CEO John Kobs, Intercom founder Des Hanrahan, Tinder founder Justin Mateen and several others.

Search Background

Despite the recent successful close of their Series A, the founding CTO decided to step away from the business for personal reasons. Following on from the successful VP of Product Management search carried out by Erevena they approached the team at Erevena again to help them in their search for a technology executive who could take responsibility for both leading and shaping the engineering function as well as owning the technical roadmap capable of delivering their ambitious vision of transforming into an insurance carrier.


They needed someone who could provide both technology vision as well as engineering team leadership through a significant scaling journey (20 to 100).  The candidate would need to be stage commensurate in their understanding of decomposing a monolith, building all of the web based, customer onboarding platforms as well as the support systems that drive all internal tooling from customer care to pricing policies and underwriting risk.


Erevena identified and placed William Kaper, the legendary ex-Amazon executive who was a veteran of building up engineering organisations in both Seattle and then East Coast based ecommerce acquisitions. Mostly recently he was VP Engineering at Root Insurance, helping to scale the company to IPO, doubling their engineering team to 250.  The value of a CTO with the scale that could take Huckleberry all the way through IPO (from settler into town planner) was a significant bonus.

Bryan O’Connell

Co-founder & CEO

The Erevena team was an incredible partner on this search, finding us a world class candidate in record time. The team obviously took the time to understand our business, but I was particularly impressed that they also understood my personality and found a leader that I would gel with and work well with. The net result was an executive who I’ve no doubt can be a leader for our organization through IPO and beyond.


Sam didn’t just source a great candidate, he also played the role of a trusted talent advisor, providing input and advice at every stage of the process. He was always available at a moment’s notice and was great to work with throughout.


I was also very impressed with the depth of proprietary technology and market knowledge native to Erevena. For any role and market, they can quickly get to a precise analysis of all available candidates. As I continue to build out my executive team, I will definitely partner with Erevena again.

Our expert

Sam Wilkins, Partner

Specialisms: Engineering leadership in all technology driven domains, Product leadership for SaaS and FinTech

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