We’re on a mission to give small business owners back time

VP Operations

San Francisco, CA

About Huckleberry

Huckleberry is rebuilding small business insurance from the ground up. In a multi-trillion dollar industry where paper forms and fax machines still predominate, and customers are wasting countless hours navigating byzantine processes, we provide small business owners with the capability to manage all of their insurance needs through a single, elegant interface. Our team is rethinking every aspect of the experience, from pricing, to underwriting to claims.

We're backed by Tribe Capital, Uncork Capital, Crosslink Capital, e.ventures, Postmates CEO Bastian Lehman, Apartment List CEO John Kobs, and several others. With a strong technology baseline and great early traction, we have plans to more than triple headcount in 2020. We believe that our team is uniquely positioned to build a massive business and a new national brand in insurance. This is a great opportunity for a VP Operations who has the heart of an entrepreneur, the brain of an operator and a proven track record in execution. In addition to managing the day-to-day operations of the business, the VP Operations will be a key member of the executive team, and a thought partner for the CEO and CTO.


You’ll be responsible for end-to-end company operations, including ownership of Insurance Operations, Customer Support, Finance, HR and Facilities.

  • Insurance Operations: Delivering an elegant insurance experience is far from easy. It can often involve complicated transfers of data, compliance materials and payments between Huckleberry and our insurance and reinsurance partners. You’ll be responsible for managing the insurance operations team as they work to ensure everything goes right “under the hood”.
  • Customer Support: You’ll have total control over our customer support system, including reevaluating any procedures or software choices, and putting in place new procedures where they don’t already exist. You’ll work closely with our engineering and product teams to provide input on the processes that should be automated and the custom tech that we need to build for our support reps.
  • Finance: In partnership with internal resources and external consultants and vendors, you’ll manage all aspects of our finance function, including billing and collections, accounts payable, payroll and forecasting.

While your input will be valued where possible, the CEO will continue to take the lead on executive recruiting, strategy, fundraising, partnerships, setting culture, managing relationships with insurers and reinsurers, and developing new insurance products.


  • You know what a world class sales and customer support function looks like, either because you’ve built one yourself or because you’ve seen one at close quarters.
  • 7+ years of total professional experience.
  • Experience in a leadership role at a startup as it scaled from Seed/Series A to Series B or beyond.
  • Experience recruiting, training and managing large teams.
  • Executive level skills in communication and leadership.
  • Sufficient knowledge of the accounting, legal and HR issues facing startups to manage the internal or external resources responsible for those areas.
  • A data-driven approach to decision making including budgeting and forecasting skills.

Ideal Candidate

  • Experience in SMB SaaS.
  • Insurance expertise can be an advantage, although we are trying to bring a fresh perspective.
  • CPA or MBA.

Why You'll Love Working at Huckleberry

  • Comprehensive medical, dental and vision insurance with 95% of premiums paid for by Huckleberry
  • Free One Medical subscription
  • Flexible Spending Account and 401k
  • Commuter benefits
  • Paid maternity and paternity leave
  • Free daily lunch and a kitchen stocked with delicious snacks, drinks, and coffee
  • Company-sponsored happy hours and outings