Executive Assistant Contractor

About AllTrails 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. Join us! This is a U.S.based remote contract engagement. Contractors in CA, CO, OR, NY, NJ, RI, and WA are subject to additional compliance requirements. 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 $40 - $65 an hour 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. We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.