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Underwriting Lead

San Francisco / New York

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. Huckleberry is looking for an experienced and innovative Chief Underwriting Officer. As a key member of the leadership team, the CUO will be responsible for underwriting results focusing on long term profitability and growth. This position will be responsible for working with our partner carrier in managing and ensuring compliance with the Underwriting Guidelines. As well, a key part of this role will be leading portfolio management – tracking growth, rate, retention and ultimately profitability.


  • In collaboration with our carrier partner, set underwriting strategy, policy, and procedures for selection of risk.
  • Manage and oversee the account review process and develop the staff necessary in the underwriting unit to achieve underwriting goals.
  • Ensure sound underwriting decisions through a robust audit process and training.
  • Develop carrier relationships, oversight of quotation process, and maintenance of management reporting necessary to support the underwriting unit.
  • Coordinate new product development and product refinement.
  • Monitor key performance indicators for new business and renewals – rate, retention, sold to benchmark and overall profitability.
  • Manage and oversee total results for the company and necessary underwriting standards and plan to achieve overall company objectives for all lines of business.
  • Supervise education of staff to enhance skills in underwriting as well as market knowledge and mentor underwriters and administrative staff.


  • Bachelor’s degree and at least ten years of experience in underwriting property and casualty products in insurance industry and/or an equivalent combination of education and experience.
  • In depth knowledge of small commercial insurance.
  • Multi-line experience in underwriting including knowledge of underwriting manuals and rate and form filing.
  • Experience and knowledge in multi-line product forms, development, and design.
  • CPCU and/or CIC Designation preferred.

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