Executive Assistant Contractor

AllTrails is the app for exploring the outdoors. We help people spend more time outside by connecting them to their next adventure. AllTrails is home to the world’s largest outdoor community, with members and trails around the globe, and supports inclusive access to nature. Every day, we solve incredibly hard problems to get more people outside, for their wellbeing and the collective care of the natural world.

AllTrails is looking for an Executive Assistant to support the CEO and Executive Team. This role will help manage the C-level team, including calendar management, serving as a Board of Directors point of contact, and planning and scheduling events and travel for executives.

This is a U.S.-based remote contract engagement, expected to be 15–20 hours per week for 4–6 months. Contractors in California, Colorado, Oregon, New York, New Jersey, Rhode Island, and Washington are subject to additional compliance requirements. The fixed-term engagement is listed as November 23, 2026 to April 30, 2026, with a stated duration of five months.

AllTrails is proud to be an equal opportunity employer. The company celebrates diversity and is committed to building a team that represents a variety of backgrounds, perspectives, and skills. AI tools may support parts of the hiring process, but final hiring decisions are made by humans.

• 5+ years of experience as an Executive Assistant, ideally supporting a VP or C-suite executive.
• Contractors must install the Vanta Agent to verify basic security settings.
• Must use macOS 11+ or Windows 10/11 Pro (64-bit).

• Manage calendars for three executives, owning day-to-day scheduling, prioritization, and coordination for the CEO and two additional executives, and protecting time for high-impact work.
• Track, organize, and submit expense reports on behalf of executives.
• Coordinate executive travel by booking flights, ground transportation, and accommodations, anticipating needs, and managing changes.
• Serve as the primary point of contact for internal AllTrails Board of Directors meetings, managing logistics, materials coordination, and attendee communications.
• Coordinate external board meeting logistics for the CEO, including scheduling, preparation materials, and follow-up.
• Schedule cross-functional meetings with teams across People, Finance, Marketing, and Engineering, ensuring stakeholders are aligned and prepared.
• Collaborate with executives and the PM team to plan and execute a multi-day Q1 extended leadership offsite.