Executive Assistant

Fleetio

15d•Remote

About The Position

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.

Requirements

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.)

Nice To Haves

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

Responsibilities

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
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.)
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
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

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 #LI-REMOTE