Description
About Outdoorsy Group
Outdoorsy Group is seeking a dynamic and entrepreneurial General Manager (GM) of Auto & Mobility to lead the company’s strategic expansion in the auto and mobility sector. This executive will own and scale all aspects of the auto strategy across Pro, Peer-to-Peer and commercial vehicle marketplaces, build and manage external partnerships, and champion a high-performing ecosystem of professional (Pro) fleet operators. This is a senior leadership role, reporting directly to the CEO.The company offers a complete Mobility-as-a-Service (MaaS) solution, uniquely combining our Wheelbase fleet management software, Roamly embedded insurance products, and a high-performing marketplace platform that connects vehicle supply with global demand.
This vertically integrated ecosystem empowers individual owners, professional operators, and mobility partners to manage, insure, and monetize fleets seamlessly—delivering everything needed to launch, scale, and operate a modern mobility business on a single platform.
About the Role
This is a global leadership role with P&L ownership and responsibility for growth across North America, Europe, and Asia-Pacific. The GM will be tasked with unlocking scalable business models and operational execution from the U.S. to Canada, Europe, and key growth markets across AsiaPac.The ideal candidate will bring deep domain expertise in mobility, auto marketplaces, or fleet operations, coupled with exceptional strategic thinking, operational rigor, and a passion for driving output and inciting action at the intersection of travel, vehicles, and technology.
Requirements
Key Responsibilities
1. Strategy & Leadership
- Own and refine the multi-year strategy for Outdoorsy Group’s Auto & Mobility business.
- Define and execute growth plans across peer-to-peer, commercial fleets, and B2B verticals.
- Partner cross-functionally with Product, Marketing, Insurance (Roamly), Operations, and Finance to drive execution.
2. Marketplace Management
- Lead the growth and optimization of Outdoorsy’s auto marketplace, including demand generation, supply growth, conversion, and unit economics.
- Develop and scale category-specific experiences for car rentals, campervans, and other emerging vehicle types.
- Monitor and improve marketplace liquidity, pricing dynamics, and fleet quality.
3. Fleet Operator (Pro) Ecosystem
- Build and support a thriving Pro community of fleet operators and commercial vehicle hosts.
- Oversee the development and distribution of Pro Tools, including fleet management, pricing optimization, and insurance integrations.
- Establish programs and incentives to drive Pro success, retention, and advocacy.
4. Strategic Partnerships
- Identify, negotiate, and manage strategic partnerships with OEMs, fleet management companies, vehicle suppliers, and other travel or sharing economy platforms.
- Explore and integrate with third-party marketplaces to syndicate supply or demand.
5. Cross-Platform Integration
- Collaborate with the Roamly team to unlock insurance innovations tailored to the Auto & Mobility segment.
- Align with the Outdoorsy Destinations and Product teams to deliver cohesive customer experiences across platform touchpoints.
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Qualifications
- 10+ years of experience in marketplaces, mobility, fleet management, or a related field.
- Proven P&L ownership and experience scaling consumer or B2B2C businesses.
- Deep understanding of vehicle-based marketplaces, car-sharing, or transportation platforms.
- Experience working with commercial operators, large vehicle fleets, marketplaces or franchised businesses.
- Strong start up mindset with the ability to drive execution in fast-paced environments.
- Excellent leadership, communication, and team-building skills.
- Data-driven decision-maker with comfort navigating ambiguity and building from 0 to 1.
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Bonus
- Prior experience in a dual-sided marketplace (e.g., Airbnb, Turo, Getaround, Uber, Outdoorsy, etc.)
- Exposure to mobility insurance, telematics, or embedded fintech products.
- Background in building community programs or SaaS tools for SMBs or prosumers.
- Passion for outdoor travel, road trips, and the future of mobility.
Benefits
Benefits & Perks:
- Opportunity to contribute to a high-growth, mission-driven company.
- Competitive salary and equity in one of the world’s fastest-growing companies.
- Comprehensive health and welfare benefits.
- 401(k) match to help secure your future.
- Flexible PTO to promote work-life balance.
Salary: $195,000 - $210,000/yr DOEOutdoorsy Group is a mission-driven company reshaping how people experience the outdoors and travel. With a multi-platform portfolio spanning marketplaces, insurance business (Roamly), and real estate (Outdoorsy Destination Network), we are creating the infrastructure for a new kind of adventure economy. As GM of Auto & Mobility, you’ll have the opportunity to drive outsized impact and shape the future of mobility-driven travel.
