Executive Assistant

Fleetio is a modern software platform that helps thousands of organizations worldwide 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. We raised $450M in our Series D funding round in March of 2025 and are on an exciting trajectory as a company. Fleetio is also a proud founding member of the Rails Foundation!

We’re seeking an energetic and detail-oriented Executive Assistant who’s excited to support senior executives at Fleetio and serve as a trusted partner in their day-to-day work. This role sits at the center of a dynamic SaaS organization and plays a meaningful part in helping leaders stay focused, prepared, and effective.

You’ll gain exposure to special projects and confidential initiatives, while spending most of your time doing what matters most—keeping calendars optimized, travel seamless, meetings well-run, and relationships thoughtfully supported.

This role is perfect for someone who enjoys juggling complex schedules, anticipating needs, and creating a seamless experience that helps executives stay focused and effective. You’ll support executive leaders in the MST and EST time zones and travel occasionally for key meetings. The role reports to the VP of People and is fully remote within the United States.

• 3+ years of experience as an Executive Assistant or in a similar administrative support role
• Experience supporting senior leaders in a fast-paced or high-growth environment
• Strong organizational and time-management skills with excellent attention to detail
• Clear, professional written and verbal communication skills
• High level of discretion and confidentiality
• Ability to pivot quickly, manage multiple priorities, and operate independently
• Proficiency with modern tools (Google Workspace, Slack, Asana, Notion, Zoom etc.)

Bonus

• If you describe yourself as tech-savvy and love incorporating technology into day-to-day work
• Experience supporting multiple executives simultaneously
• Background in project management, operations, or strategic communications

• Executive Support & Coordination
  • Manage complex calendars across time zones, ensuring alignment with strategic priorities
  • Act as a gatekeeper—triaging communications, prioritizing requests, and managing the flow of information
  • Plan and coordinate complex domestic and international travel, including flights, accommodations, transportation, and itineraries
  • Provide real-time support for travel changes or disruptions, identifying quick solutions as needed
  • Maintain flexibility and availability outside standard working hours to support executive travel needs
• Meeting, Event & Administrative Support
  • Coordinate leadership meetings, offsites, dinners, and executive events
  • Attend select meetings to capture action items and ensure follow-ups are documented and tracked
  • Maintain organized meeting notes, agendas, and follow-up documentation
  • Prepare executive-level correspondence, presentations, and documents
  • Coordinate internal and external meetings, including agendas, preparation materials, and follow-up actions
  • Anticipate meeting needs, including preparation time, materials, context, and attire
  • Perform pre-meeting checks to confirm attendance, agendas, and logistics (room setup, food, beverages, A/V, etc.)
• Relationship Management
  • Support executive relationship management by tracking key contacts, follow-ups, and touchpoints
  • Assist with thoughtful outreach, scheduling, and follow-through for external partners, investors, and stakeholders
  • Serve as a professional point of contact for high-priority external communications
  • Build strong, trust-based relationships across the organization
• Special Projects & Initiative Ownership
  • Lead or co-lead cross-functional projects—scoping work, building timelines, coordinating stakeholders, and delivering outcomes
  • Step in to support or manage programs that require short-term leadership or coordination
  • Handle sensitive information with discretion and produce consistently high-quality work