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

Head of Sales

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 Uncork Capital, Crosslink Capital, e.ventures, Postmates CEO Bastian Lehman, Apartment List CEO John Kobs and several others.  We’re looking for aggressive, ambitious operators that want to accelerate their career at a company that is changing the face of an old-school industry. The right candidate for this role will have a passion for startups, strong communication skills and a desire to prove themselves while exceeding revenue goals.


  • Manage and grow the sales team, including training, motivating, coaching, and performance managing junior associates.
  • Own the customer pipeline from marketing lead through to closing.
  • Create, build and implement processes, systems and tools to aid and empower your team.
  • Interact closely with the marketing, product and engineering teams to surface customer feedback for rapid integration into both the core product and ongoing marketing campaigns.


  • 5+ years of professional experience, with at least 4 years in a sales or customer operations leadership function.
  • Startup experience highly preferred (experience selling to SMBs is a bonus).
  • Experience recruiting, developing, and managing sales teams.
  • Ability to define and maintain KPIs and other metrics that define team and customer success.
  • Excellent written and spoken communication skills in English – you will be responsible for ensuring that your team’s communications with customers meet the company’s high bar for professionalism.

Ideal Candidate

You are a highly analytical customer-focused leader experienced in growing top performing teams and improving operational processes. You’ve built up a sales team in the past and know what it takes to attract, retain, and mentor high quality talent. You’re comfortable managing colleagues that are early in their career, and are adept at inspiring less experienced team members to deliver high quality work. You have high standards for excellence and feel a great sense of satisfaction when every customer interaction reinforces the company’s brand promise. You’re an aggressive, competitive operator, determined to drive your team and the company to continued success.