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.

Our Products

The company currently offers pay-per-mile car insurance. Customers who drive less than 12K miles a year save on average over $700 annually. The consumer opportunity is vast. About 65% of US drivers drive fewer than 12k miles per year. It’s everyone from urban millennials and suburban families commuting on public transit, to retirees driving close to home, remote employees, and the eco-conscious. 

Through its Enterprise unit, Metromile licenses its Fraud Detection, and claims AI platform to insurers around the globe. And, as the only insurer with 100% continuous telematics and a first of its kind AI-driven virtual claims system, the company is well positioned to play a key role in the future of mobility ecosystem. 


Metromile has raised approximately $291 million in funding (Series A through E) and is backed by top tier Silicon Valley Investors including NEA, Index, Future Fund and First Round Capital. Additionally, the insurance industry has taken note and Metromile’s Series D fundraise was led by Intact, the largest Canadian insurer; our Series E was led by Tokio Marine, the largest Japanese insurer.

The Role

As the Chief People Officer, you will be part of the executive leadership team and report directly to the CEO. Your work will be instrumental for Metromile’s growth, all while ensuring our culture and values flourish.

This position requires an extremely perceptive person who is capable of relating to different levels in the organization. You will be responsible for scaling our company culture, as well as leading and managing a team of talented and mission-driven people in SF, Arizona and Boston. Metromile has a strong people culture that it wants to further deepen under your leadership.

You are forward-thinking and know how to achieve short-term goals while implementing and scaling processes and tools for the long-term. With your passion for people and performance, you’ll navigate the complex issues of rapid growth while promoting a people-focused, solutions-oriented approach to ensure Metromile’s future success.

You Will:

  • Lead the People, Talent and Administrative teams where we do our best, most impactful work.
  • Be a trusted strategic partner and advisor to the CEO, senior leadership and management teams
  • Serve as a key leader within the Executive team, providing business insight and ensuring buy-in to key decisions, agreement on strategic direction, and alignment of cross-functional resources and activities
  • Bring an analytical approach to continue building Metromile as a whole, while aligning Metromile business objectives with the broader people strategies
  • Support leadership on developing the culture and driving employee engagement by optimizing our employee engagement and feedback systems
  • Act as coach/consultant to senior leaders on HR related issues while balancing your role as an employee advocate
  • Partner closely with the Comms team on employer brand, internal communications, employee engagement, and Best Place to Work awards and rankings 
  • Be an informed leader on trends regarding the future of work, and ensuring Metromile is perceived as an employer of choice 
  • Champion the continued development of culture and encompassing Metromile’s values
  • Design org structures, leadership development plans and bench strategies
  • Provide leadership on HR programs and processes as we grow, including:
    • Compensation, Benefits and Incentive plans
    • Performance Feedback
    • Learning & Development 
    • Compliance and Risk Management
    • Diversity and Inclusion
    • Tools and Technology 


  • A progressive, entrepreneurial spirit combined with at least 10+ years of related experience
  • Significant experience leading and building high performing teams in a combination of General HR, Talent Acquisition and related disciplines
  • Broad and deep experience as an HR Business Partner supporting executives and/or senior leadership
  • Proven experience leading and partnering with a geographically dispersed workforce
  • A track record of improving retention within highly competitive job markets
  • A proven track record of success in scaling a company’s core culture and values from the early stages through the growth stages
  • Strong project management, organization, and communication skills backed with a data-driven approach
  • The ability to handle sensitive situations and maintain confidentiality
  • Creative and resourceful problem-solving skills
  • Excellent communication skills - written, verbal and interpersonal - with an ability to tailor communication style to diverse audiences
  • Drive to execute initiatives with limited resources and roll-up your sleeves attitude to achieve desired results

What’s in it for you

  • Competitive salary plus equity
  • 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 & PC equipment available and adjustable workstations

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

Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.

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