Metromile is hiring an

Executive Assistant

San Francisco, United States

About Us

Metromile is a start-up with a soft spot for cars, a roadmap of great ideas, and a desire to seriously challenge the status quo. You could think of us as the David to the auto insurance industry's Goliath. Our product leverages mobile technology, automotive telematics, and data-driven applications to make a car's data accessible AND useful to modern drivers.

Our app crunches a ton of data: trip stats, decoded check-engine lights, street sweeping alerts, and car location. For those who don't log a lot of miles each year, we offer the revolutionary alternative of pay-per-mile insurance.

Why pay for the all-you-can-eat buffet when all you eat is the salad?

We're just getting started, so come disrupt more age-old traditions with us. Buckle up and get ready to drive with Metromile.

About the Executive Assistant Role

Metromile is seeking an engaging and dynamic Executive Assistant to support the Chief Marketing Officer and Chief Technology Officer. You will advise and manage all calendars from scheduling to meeting briefs and agendas. While acting as a gatekeeper, you will prep each executive for their upcoming meetings and help them manage their time effectively. You will partner with the CMO and CTO to facilitate communication across their teams and ensure company and executive priorities are being met. At times, you will take on additional projects, that may require you to do research and advise as needed.

You are:

  • Prepared for anything. You are always thinking one step ahead and strive to go above and beyond what is asked of you.
  • Driven. You love being busy and put in hard work to complete tasks. Leaving something partially done drives you crazy.
  • Organized. If we asked for your Proof of Insurance card, you’d find it in less than 2 minutes.
  • Solutions oriented. When identifying a problem, you’re already considering a number of creative solutions. 
  • Naturally curious. You're innovative, extremely creative and always asking questions to learn more.
  • Independent, but a Team Player. You can operate well independently with little guidance or direction, but can also work well with a team.

Your responsibilities:

  • Provide support for the Chief Marketing Officer and Chief Technology Officer.
  • Perform a variety of administrative tasks including calendar management, travel arrangements, and meeting planning.
  • Assist with task management. Recognize what tasks can be delegated and take on projects as needed.
  • Maintain confidence and protect operations by keeping information confidential.
  • Provide occasional support for the rest of the executive team.
  • Provide coverage and fill in for the Executive Assistant to the CEO as needed.
  • Resolve administrative problems by coordinating preparation of reports, analyzing data, and identifying solutions.

Position requirements

  • 4+ years of administrative experience preferred.
  • Excellent organization, creative thinking, and analytical skills.
  • Ability to maintain confidentiality in all business matters.
  • Experience managing multiple time sensitive projects from conception to completion.
  • Strong computer skills, including familiarity with Google Apps and Microsoft Office suite.
  • High level of confidentiality, discernment, and judgment.
  • Experience in a start-up environment preferred.


  • Competitive salary plus equity
  • Benefits (Health, Dental, Vision)
  • Transportation and gym benefits
  • Catered lunches and a fully stocked kitchen
  • Monthly social events (Trivia nights, skeeball, ropes course, etc)
  • Mac equipment and ergonomic work station, customized to your specs