About Us

On the off chance you've thought about insurance, it's likely because you've insured something you love, not because you loved your insurance company. Metromile is out to change that. As an insurtech powered by data science and customer centric-design, we’re building a community of drivers who come for the savings and stay for the experience.

With technology at its core, Metromile is reimagining insurance to make it fairer and actually delightful. We’re obsessed with savings, service, and features -- street sweeping alerts, monthly mileage summaries, fuel trackers and more -- that engage a customer all along their journey.  We’re on the forefront of disrupting a $250 billion auto insurance category that has gone unchanged for over 80 years. 

Metromile’s diverse team combines the best of Silicon Valley technologists with veterans from Fortune 500 insurers and financial services giants. This management structure ensures that the business is focused on growth, customer experience and technology innovation while also balancing unit economics and profitability. The team is growing quickly across its San Francisco, Tempe, and Boston offices. Our customer service, claims, and sales teams are all based in-house in the US. 

Named a Glassdoor Best Place to Work two years in a row, our CEO consistently has a 95+ percent approval rating; nearly 90% say they’d recommend Metromile to a friend.

About the role

Metromile recently launched a new B2B business venture, Metromile Enterprise, to license its proprietary AI platform to insurance companies in the US and across the globe. We are looking for a Director of Enterprise Sales to accelerate revenue growth of this new venture.

Successful candidates should know how to build customer relationships at all levels, present to / communicate with customers at different stages of the sales process, develop materials for sales meetings, manage a sales pipeline, and assist with scoping/contract development. This role needs to communicate effectively across multiple departments and customers, have the ability to shift gears at a moment's notice and enjoy the challenges of executing on a sales strategy and exceeding quota for a new business venture. If this sounds like a challenge you would enjoy learning more about—we want to hear from you!

You Will

  • Own the entire sales cycle from lead to close, with support from leadership team
  • Establish lasting relationships with senior executives and key decision-makers
  • Help educate customers on the value of Metromile Enterprise throughout the adoption cycle, including communicating pricing options, implementation plans, and contract terms
  • Develop and execute on creative strategies to build pipeline, accelerate sales cycles and optimize revenue
  • Work with internal Metromile Enterprise stakeholders to assess feasibility, timelines, etc.
  • Requires U.S. and international travel.  

About You:

  • Prior success (5+ years) selling large enterprise software deals to P&C insurance carriers at the CXO level
  • A track record of setting and achieving ambitious goals 
  • The desire to build and be part of a great culture and a winning team
  • A track record of deep P&C insurance relationships 
  • Superior presentation and negotiation skills 

Nice to Haves:

  • Prior experience selling *claims* technology to P&C insurance carriers

What’s in it for you

  • Competitive salary plus aggressive commission structure
  • Robust benefit options (health, dental, vision, 401K)
  • Commuter and well-being benefits
  • Generous parental leave
  • Catered lunches and a fully stocked kitchen
  • Monthly social events (Movies, game nights, park days, etc.)
  • Mac equipment and adjustable workstations

Metromile is an Equal Opportunity-Affirmative Action Employer – Minority / Female / Disability / Veteran / Gender Identity / Sexual Orientation.

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