Executive Assistant

Posted Aug 2

Executive Assistant to the CEO


We're looking for a remarkable Executive Assistant to work with our Founder & CEO, Tony Summerville. This is not a traditional administrative assistant role. This is a challenging yet rewarding role that requires a broad skill set and a resourceful attitude. You'll become an important partner to Tony and contribute to the success of Fleetio at the highest level.

Fleetio is a modern software platform that helps thousands of organizations around the world manage their fleet operations. Transportation technology is a hot market and we’re leading the charge with raving fans and new customers signing up every day.

In this role, you will clear bottlenecks and improve the CEO's velocity by tracking his commitments, structuring his time around the most important priorities, and ensuring fast follow-through on his responsibilities. We consider it essential to the company’s future success. Be sure to mention coffee in your cover letter so we know you read this.

What you'll be doing

  • Closely manage the CEO's time based on his priorities. Have confidence and sound judgment to push back on the CEO when he gets distracted from his top priorities.
  • Expertly maintain and update the CEO's calendar based on his preferences and ensure all meetings are set up for success (accurate locations, contact details, links, etc).
  • Track action items committed to in meetings and create follow-up emails when applicable.
  • Process emails for the CEO and indicate the priority of emails in the inbox. Draft email responses when possible that the CEO can edit and send.
  • Consistently stay up-to-date on task management and communicate effectively regarding what is most important. Execute tasks that have been delegated to you by the CEO.
  • Help manage and grow both business and personal relationships by proactively identifying and executing opportunities to reconnect with (and even delight) various contacts and acquaintances.
  • Perform various research related to CEO's work and personal projects & priorities.

What's in it for you

  • You'll be a valued partner to the CEO and get an intricate view into the executive-level operations of a fast-growing technology business.
  • You'll foster relationships across lots of different people while solving interesting problems.
  • Be a part of an incredible operations team of "A" players who go above and beyond to make Fleetio a successful company. We’re a customer-centric team with a great product, excellent support, and countless happy customers.


  • Incredibly clear communicator, both written and verbal: You must be able to write and speak extremely well using clear language.
  • Self-confident and impressive: You can communicate professionally and confidently with seasoned business executives and contacts.
  • Trustworthy: You are a highly principled person. Integrity is an important value you fundamentally adhere to.
  • Attention to detail: Anyone who knows you would describe you as super detail-oriented. You love getting the details right and it bugs you if others don't.
  • Technical-savvy: Must embrace and not be intimidated by technology. You understand how to leverage systems and tools like Asana, Slack, Notion, Gmail, etc. to make you more productive and effective.
  • Resourceful: You are a clever problem-solver who thinks one step ahead of most people.
  • Intelligent: You're a lifelong learner and genuinely curious about things. You thrive on advancing your skills and knowledge and are self-motivated to learn new things on your own.


  • 100% coverage of employee health and dental insurance (50% family)
  • 401(k) + match
  • Company stock options
  • Vision, STD & LTD
  • Dependent Care FSA and Medical FSA
  • Generous PTO, Company Holidays & Floating Holiday
  • Maternity/Paternity leave
  • Community service funds
  • Mac laptop
  • Professional development funds
  • Health and wellness incentives
  • Remote working friendly since 2012

Fleetio provides equal employment opportunities to all employees and applicants and prohibits discrimination and harassment. We celebrate diversity and are committed to creating an inclusive environment for all. All employment is decided on the basis of qualifications, merit and business need.

This application is not intended to and does not create a contract or offer of employment. Employment with Fleetio is at will.