Executive Assistant Contractor

Team: Executive

Location: Remote

Commitment: Contract

Workplace Type: remote

About the Role

AllTrails is looking for an Executive Assistant to support the CEO and Executive Team at AllTrails. This role will help manage the C-level team, including calendar management, BoD POC, planning and scheduling events/travel for Execs.

This is a remote, contract position with an expectation of 15-20 hours per week for 4-6 months.

Due to high candidate volume and to ensure our hiring team has sufficient time to give every application the attention it deserves, we have set a closing date of October 27th for this position.

What you’ll do

• Manage calendars for 3 executives: Own day-to-day scheduling, prioritization, and coordination for the CEO and two additional executives, ensuring time is protected for high-impact work

• Handle expense reporting: Track, organize and submit expense reports on behalf of executives

• Coordinate executive travel: work directly with CEO to book flights, ground transportation and accommodations, anticipating needs and managing changes as they arise 

• Serve as POC for AllTrails Board Meetings: Be the primary point of contact for internal AllTrails Board of Directors meetings, managing logistics, materials coordination, and communication with attendees

• Serve as POC for External Board Meetings (CEO): Coordinate external board meeting logistics for the CEO, including scheduling, prep materials and follow-up

• Schedule cross-functional meetings: Partner with teams across People, Finance, Marketing, and Engineering to facilitate executive meetings and ensure the right stakeholders are aligned and prepared

• Plan Q1 extended leadership offsite: Collaborate with executives and the PM team to plan and execute a multi-day offsite for the extended leadership team

What you bring

• 5+ years of experience as Executive Assistant, ideally supporting VP or C-Suite.

• Contractors must install the Vanta Agent to verify basic security settings and use macOS 11+ or Windows 10/11 Pro (64-bit)

Logistics

• Role title: Executive Assistant Contractor

• Team/function: Executive 

• Compensation: $40-65/hr 

• Engagement type: Fixed-term contract

• Expected hours: 15 to 20 hours per week 

• Duration: November 23, 2026 to April 30, 2026 (5 months)

• Location: Remote 

AllTrails is proud to be an equal opportunity employer. We celebrate diversity and are committed to building a team that represents a variety of backgrounds, perspectives, and skills.

By submitting my application, I acknowledge and agree to AllTrails Job Applicant Privacy Notice.