Executive Assistant

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.

A little about us…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. We raised $450M in Series D in June of 2025 and are on an exciting trajectory as a company. Fleetio is also a proud founding member of the Rails Foundation!

More about our team and company:

• Fleetio overview video: https://www.youtube.com/watch?v=IlvIbwZT3oU
• Our careers page: https://www.fleetio.com/careers

Who you are

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 EST time zone and travel occasionally for key meetings. The role reports to the VP of People and is fully remote within the United States.

Your impact

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

Your experience

• 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

Benefits

• Multiple health/dental coverage options (100% coverage for employee, 50% for family)
• Vision insurance
• Incentive stock options
• 401(k) match of 4%
• PTO - 4 weeks (increases at year two!)
• 12 company holidays + 2 floating holidays
• Parental leave - birthing parent (16 weeks paid) non-birthing (4 weeks paid)
• FSA HSA options
• Short and long term disability (short term 100% paid)
• Community service funds
• Professional development funds
• Wellbeing fund - $150 quarterly
• Business expense stipend - $125 quarterly
• Mac laptop + new hire equipment stipend
• Fully stocked kitchen with tons of drinks snacks (BHM only)
• 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.

If you have a disability or a special need that requires an accommodation to fill out the online application, please let us know by calling (205) 718-7500.