Chief Commercial Officer

Outdoorsy • Austin, TX

1d

About The Position

The Paradigm Shift The mobility industry is undergoing its most radical transformation in a century: the shift from Human-Operated to Software-Defined, Autonomous Mobility. As the world moves toward Level 4 and Level 5 Full Self-Driving (FSD), the concept of risk changes entirely. Accidents will no longer be matters of human error, but of software edge cases and sensor fidelity. Therefore, the future of insurance is not demographic profiling—it is algorithmic underwriting based on live vehicle telemetry. We are entering a new era. One that will prove to be the largest disruption in the history of insurance and mobility. The insurance industry has been built on a single, fundamental premise: that human behavior is the primary variable of risk and this is how insurance is priced and issued. But that premise is expiring. Austin is ground zero for this revolution where growing fleets of Waymos and Robotaxis operate With the maturity of Full Self-Driving (FSD) and Level 5 autonomy, the human is going to be removed from the mobility equation. When the car becomes the operator, the car must also become the customer. This requires an evolution for Roamly’s business model. We are going to adjust from insuring human operators to insuring autonomous decisions, where risk is priced on software quality, not driver history. Eg, we must underwrite for the code not the human. The Death of the “Operator” Risk is no longer about who is in the car, but what version of the software is running and how the hardware and software systems are performing. In an autonomous future, the concept of a human “operator” will become a legal fiction. If the vehicle controls acceleration, braking, and steering 100% of the time, the human inside is no longer the operator. About the Outdoorsy Group The Outdoorsy Group is the world’s leading outdoor travel and hospitality ecosystem. Our mission is to restore our relationship with the outdoors—and with one another—by making the life-changing experience of outdoor travel accessible to everyone. What started as Outdoorsy.com , the largest and most trusted peer-to-peer RV rental marketplace, has evolved into a multi-vertical powerhouse. Today, our group integrates marketplace technology and a sophisticated AI Insurance business that is redefining insurance in the mobility and rec lines markets. Roamly: Insurance Built for Adventure Roamly is the first AI based insurance platform specifically engineered to remove the barriers to the sharing economy. For decades, traditional insurance policies prevented RV owners from renting their vehicles, leaving millions of assets idle. Roamly solved this by developing "rent-ready" insurance, allowing owners to unlock new revenue streams while providing travelers with the peace of mind they need. Roamly has grown fast and now offers more than 22 products serving the mobility markets, recreational lines and marketplace economy. The company won the Celent 2025 Innovation Award for our AI Rater and will expand to international markets. As a Lloyd’s of London Coverholder , Roamly has grown beyond the Outdoorsy ecosystem to become a dominant player in specialty insurance. It now provides AI-first coverage for RVs, carsharing fleets, boats and motorcycles, offering a seamless "quoteto- bind" experience that is lightyears ahead of legacy providers. We recently launched Myles, our Agentic AI Digital Employee . Myles represents the next frontier of the Outdoorsy Group’s commitment to a seamless, "always-on" customer experience. As Roamly’s flagship Agentic AI, Myles is far more than an AI chatbot; he is an autonomous digital teammate who handles complex, multi-step workflows inherent in specialty insurance. Whether it’s instantly qualifying leads, guiding a customer through a nuanced "quote-to-bind" journey for a custom DIY van, or proactively managing policy updates across various platforms, Myles operates with a level of context-awareness and decision-making authority that mirrors a human expert. For our CCO, Myles serves as a primary proof point of how we use proprietary AI to eliminate friction in the sharing economy, allowing our human teams to focus on high-impact strategy while Myles ensures that every customer’s needs are met in real-time, 24/7. Roamly Labs: Our Innovation Engine At the heart of our technical superiority is Roamly Labs . This is our dedicated AI-first innovation hub and sandbox where we architect the future of insurance, autonomous mobility and marketplace dynamics. Roamly Labs focuses on: AI-Driven Actuarial Science: Developing proprietary tools like our AI Actuarial Rater, which has won industry awards for reducing rate-deployment timelines from months to days. Autonomous Mobility: bridging the gap between hardware-led autonomous vehicle (AV) evolution and the commercial infrastructure required to run them profitably. Embedded Distribution: Engineering the APIs that allow partner marketplaces and dealerships to integrate insurance at the point of sale. Identity & Risk Resolution: Leveraging massive data sets to create a "Customer 360" view, ensuring our ecosystem is safer and more personalized for every user. Agentic Systems – more Agents driving recursive leverage throughout the systems, with continuous learnings and improvements. In this role, you won't just be marketing a marketplace or an insurance platform. You will be the architect of multiple initiatives that connect the emotional freedom of the Outdoorsy traveler with the invisible, cutting-edge security powered by Roamly’s technology and our autonomous solutions to bring autonomous mobility into marketplaces across multiple geos. Roamly is an AI first full-stack digital insurance platform built for the specialty lines and mobility markets. Roamly is at the heart of the ecosystem and operates as a whollyowned subsidiary of Outdoorsy —the world’s leading online outdoor travel marketplace. At our beginning, we solved a problem no one else could: we eliminated the commercial use exclusion clause that stopped RV owners from renting out their vehicles. We have evolved into the mobility markets and the broader recreational lines insurance markets. We have recently taken Autos online including EVs and Autonomous vehicles. Roamly is an AI-first, data-driven insurance platform empowering the modern mobility economy. The company’s proprietary rater won the 2025 Celent innovation award for our AI based rater, which is highly proprietary. From embedded insurance products for marketplaces to global travel protection and enterprise SaaS solutions, Roamly is redefining how the world insures mobility and adventure. In 2025, we were appointed a Lloyd’s of London Coverholder, and this gives us the ability to expand margins and grow even more rapidly across North America and Europe. The company is profitable and growing at a 90% year on year growth rate. We are looking for a visionary CCO to lead our next phase of growth and expansion into international markets. The Opportunity We are seeking a Chief Commercial Officer who lives at the intersection of storytelling and high performance growth. You will be marketing a vertically integrated mobility ecosystem with an AI insurance platform that is now building digital employees (Agentic Agents). As CCO, you will own the end-to-end marketing strategy for the company and driving customer acquisition for our direct-to-consumer (DTC) lines while supporting our B2B/Enterprise partnerships. You will own Go to Market strategies and tactics. You will own Direct to Consumer, Agency, and Partnerships, MGAs, Carriers, Embedding Ecosystem Partners. You will oversee our rapid growth and lead a world class Marketing organization spanning Performance, Lifecycle, Creative, Sales, Customer Success, Research, Comms, PR, Media and Content. You will drive growth through advertising and communications using TV, Radio, Social Platforms, Facebook, Instagram, TikTok, YouTube, influencers, LLMs, Email, SEO, Content and PR. You will take a suite of highly unique products — and make them accessible, human, and essential for millions of consumers and businesses world wide. You will have global markets and preferably public company experience. A high-level CCO at a fast-growing tech company is a revenue-accountable growth architect who aligns product, brand, and demand into a scalable system.

Requirements

• The Modern Marketer: You have 15+ years of experience, with at least 5 years in a CMO, VP or other C-level role, preferably within Digital Insurance, Fintech, Mobility or Two-Sided Marketplaces.
• A Storyteller with a Quant Brain : You can critique a creative brief one minute and dissect a cohort analysis the next. You understand that brand builds trust, but data builds scale.
• A "Front-Line" Leader: You are ready to roll up your sleeves. You thrive in highgrowth environments where speed-to-market is critical, and resources must be deployed creatively.
• Ecosystem Thinker: You understand the dynamics of embedded finance/insurance and how to leverage a parent brand (Outdoorsy) to fuel growth.
• Global Mindset: Experience with international markets (specifically Europe/Canada) is a strong plus.

Responsibilities

• Build a repeatable, scalable growth engine that aligns product, brand, and revenue — without breaking unit economics.
• Market positioning and differentiation
• Category creation or category leadership strategy
• Core messaging architecture
• Executive narrative for:
• Investors
• Customers
• Press
• Analysts
• Define and execute the long-term marketing strategy to position the company as the global category leader in mobility, marketplace economy and specialty insurance.
• Evolve the voice of the Outdoorsy ecosystem—moving beyond "marketplace” and “insurance" to "Ecosystem that enables mobility and adventure."
• Serve as a key member of the Executive Leadership Team, influencing company and product roadmap, product development, and expansion into new verticals.
• Own all aspects of marketing; drive aggressive customer acquisition costs (CAC) and lifetime value (LTV) optimization across all channels (Paid Search, Social, SEO, Affiliate, and Partnerships).
• Scale our "embedded insurance" proposition, working closely with Product and Sales teams to integrate Roamly into third-party platforms, Dealerships, MGAs, online Brands and Carriers.
• Develop full-funnel strategies that convert marketplace users into long-term Roamly policyholders.
• Translate complex insurance concepts into simple, compelling narratives for diverse audiences: consumers, owners of recreational assets – RVs, Boats, Autos, DIY van-lifers, professional fleet operators, and enterprise partners.
• Lead go-to-market (GTM) strategy for new product launches, such as Autonomous Vehicles, Marketplace insurance products for EVs and Autonomous Vehicle fleets and Global Insurance Products.
• Oversee PR, Media, corporate communications, and thought leadership to elevate the company’s profile in both the Insurance, Mobility and Travel markets.
• Clear ICP definition
• Value prop clarity
• Pricing & packaging strategy
• Launch discipline
• Competitive intelligence
• Sales enablement alignment
• Build a culture of testing and attribution. Utilize our rich proprietary data (from millions of Outdoorsy customers and policyholders) to predict customer needs and personalize cross-sell opportunities.
• Oversee the marketing technology stack to ensure seamless integration between CRM (Salesforce/HubSpot), automation tools, and data visualization platforms.
• Lowers CAC
• Improves conversion
• Increases pricing power
• Attracts talent and partners
• Short-term performance marketing
• Long-term brand equity
• Performance marketing
• Product marketing
• Brand / comms
• Lifecycle / CRM
• Ops & analytics
• CEO – narrative, strategy, external messaging
• CRO / Sales – pipeline, conversion, enablement
• Product – roadmap influence, GTM timing
• Finance – budgeting, ROI, efficiency
• Legal / Comms – risk, disclosures, crisis response
• Press interviews
• Analyst briefings
• Industry events
• Crisis comms
• Partner ecosystems

Benefits

• Comprehensive Health, Dental, and Vision.
• Flexible PTO
• $15,000 annual travel credit to take trips on Outdoorsy (Go explore the product you protect!).
• 401(k) matching.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed