Chief Commercial Officer

The mobility industry is undergoing its most radical transformation in a century: the shiftfrom Human-Operated to

As the world moves toward Level 4 and Level 5 Full Self-Driving (FSD), the conceptof risk changes entirely. Accidents will no longer be matters of human error, but ofsoftware edge cases and sensor fidelity. Therefore, the future of insurance is notdemographic profiling—it is

We are entering a new era. One that will prove to be the largest disruption in the historyof 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 howinsurance is priced and issued. But that premise is expiring. Austin is ground zero forthis revolution where growing fleets of Waymos and Robotaxis operateWith the maturity of Full Self-Driving (FSD) and Level 5 autonomy, the human is goingto be removed from the mobility equation.

When the car becomes the operator, the carmust also become the customer. This requires an evolution for Roamly’s businessmodel. We are going to adjust from insuring human operators to insuring autonomousdecisions, where risk is priced on software quality, not driver history. Eg, we mustunderwrite for the code not the human.

Risk is no longer about

and

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 humaninside is no longer the operator.

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—bymaking the life-changing experience of outdoor travel accessible to everyone.What started as Outdoorsy.com, the largest and most trusted peer-to-peer RV rentalmarketplace, has evolved into a multi-vertical powerhouse. Today, our group integratesmarketplace technology and a sophisticated AI Insurance business that is redefininginsurance in the mobility and rec lines markets.

Roamly is the first AI based insurance platform specifically engineered to remove thebarriers to the sharing economy. For decades, traditional insurance policies preventedRV owners from renting their vehicles, leaving millions of assets idle. Roamly solvedthis by developing "rent-ready" insurance, allowing owners to unlock new revenuestreams while providing travelers with the peace of mind they need. Roamly has grownfast and now offers more than 22 products serving the mobility markets, recreationallines and marketplace economy.

The company won the Celent 2025 Innovation Awardfor our AI Rater and will expand to international markets.As a Lloyd’s of London Coverholder, Roamly has grown beyond the Outdoorsyecosystem to become a dominant player in specialty insurance. It now provides AI-firstcoverage 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 representsthe next frontier of the Outdoorsy Group’s commitment to a seamless, "always-on"customer experience.As Roamly’s flagship

autonomous digital teammate who handles complex, multi-step workflows inherent inspecialty insurance. Whether it’s instantly qualifying leads, guiding a customer through anuanced "quote-to-bind" journey for a custom DIY van, or proactively managing policyupdates across various platforms, Myles operates with a level of context-awareness anddecision-making authority that mirrors a human expert. For our CCO, Myles serves asa primary proof point of how we use proprietary AI to eliminate friction in the sharingeconomy, allowing our human teams to focus on high-impact strategy while Mylesensures that every customer’s needs are met in real-time, 24/7.

At the heart of our technical superiority is Roamly Labs. This is our dedicated AI-firstinnovation hub and sandbox where we architect the future of insurance, autonomousmobility and marketplace dynamics.Roamly Labs focuses on:• AI-Driven Actuarial Science: Developing proprietary tools like our AI ActuarialRater, which has won industry awards for reducing rate-deployment timelinesfrom months to days.• Autonomous Mobility: bridging the gap between hardware-led autonomousvehicle (AV) evolution and the commercial infrastructure required to run themprofitably.• Embedded Distribution: Engineering the APIs that allow partner marketplacesand 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 forevery user.• Agentic Systems – more Agents driving recursive leverage throughout thesystems, with continuous learnings and improvements.In this role, you won't just be marketing a marketplace or an insurance platform.

Youwill be the architect of multiple initiatives that connect the emotional freedom of theOutdoorsy traveler with the invisible, cutting-edge security powered by Roamly’stechnology and our autonomous solutions to bring autonomous mobility intomarketplaces across multiple geos.Roamly is an AI first full-stack digital insurance platform built for the specialty lines andmobility markets. Roamly is at the heart of the ecosystem and operates as a whollyownedsubsidiary of Outdoorsy—the world’s leading online outdoor travel marketplace.At our beginning, we solved a problem no one else could: we eliminated the commercialuse exclusion clause that stopped RV owners from renting out their vehicles. We haveevolved 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 mobilityeconomy. The company’s proprietary rater won the 2025 Celent innovation award forour AI based rater, which is highly proprietary. From embedded insurance products formarketplaces to global travel protection and enterprise SaaS solutions, Roamly isredefining how the world insures mobility and adventure. In 2025, we were appointed aLloyd’s of London Coverholder, and this gives us the ability to expand margins and groweven more rapidly across North America and Europe. The company is profitable andgrowing at a 90% year on year growth rate. We are looking for a visionary CCO to leadour next phase of growth and expansion into international markets.

We are seeking a Chief Commercial Officer who lives at the intersection of storytellingand high performance growth. You will be marketing a vertically integrated mobilityecosystem with an AI insurance platform that is now building digital employees (AgenticAgents).As CCO, you will own the end-to-end marketing strategy for the company and drivingcustomer acquisition for our direct-to-consumer (DTC) lines while supporting ourB2B/Enterprise partnerships. You will own Go to Market strategies and tactics.

You willown Direct to Consumer, Agency, and Partnerships, MGAs, Carriers, EmbeddingEcosystem Partners. You will oversee our rapid growth and lead a world classMarketing organization spanning Performance, Lifecycle, Creative, Sales, CustomerSuccess, Research, Comms, PR, Media and Content. You will drive growth throughadvertising and communications using TV, Radio, Social Platforms, Facebook,Instagram, TikTok, YouTube, influencers, LLMs, Email, SEO, Content and PR. You willtake a suite of highly unique products — and make them accessible, human, andessential for millions of consumers and businesses world wide. You will have globalmarkets and preferably public company experience.A high-level CCO at a fast-growing tech company is a revenue-accountable growtharchitect who aligns product, brand, and demand into a scalable system.

• Market positioning and differentiation• Category creation or category leadership strategy• Core messaging architecture• Executive narrative for:o Investorso Customerso Presso Analysts• Define and execute the long-term marketing strategy to position the company asthe global category leader in mobility, marketplace economy and specialtyinsurance.• 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 companyand 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 andSales teams to integrate Roamly into third-party platforms, Dealerships, MGAs,online Brands and Carriers.• Develop full-funnel strategies that convert marketplace users into long-termRoamly policyholders.

• Translate complex insurance concepts into simple, compelling narratives fordiverse 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 asAutonomous Vehicles, Marketplace insurance products for EVs and AutonomousVehicle fleets and Global Insurance Products.• Oversee PR, Media, corporate communications, and thought leadership toelevate 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 (frommillions of Outdoorsy customers and policyholders) to predict customer needsand personalize cross-sell opportunities.• Oversee the marketing technology stack to ensure seamless integration betweenCRM (Salesforce/HubSpot), automation tools, and data visualization platforms.

At scale, brand becomes a unit economics lever:• Lowers CAC• Improves conversion• Increases pricing power• Attracts talent and partnersYou will balance:• Short-term performance marketing• Long-term brand equity

You will build a team that can scale:• Performance marketing• Product marketing• Brand / comms• Lifecycle / CRM• Ops & analyticsYou know

• 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

Often the public face (or co-face) of the company:• Press interviews• Analyst briefings• Industry events• Crisis comms• Partner ecosystemsYou will be

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in a CMO, VP or other C-level role, preferably within

• A Storyteller with a Quant Brain: You can critique a creative brief one minuteand dissect a cohort analysis the next. You understand that brand builds trust,but data builds scale.•

environments where speed-to-market is critical, and resources must bedeployed creatively.•

finance/insurance and how to leverage a parent brand (Outdoorsy) to fuelgrowth.•

Europe/Canada) is a strong plus.

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have product $4 Billion in total sales by May of 2026 and growing fast. Thecompany has been profitable for the last 3 years and will achieved it’s 4th year ofprofitability in 2026.•

renting their assets and helping consumers and travelers explore the worldsafely. You are passionate about the mobility markets and especially theautonomous revolution.•

autonomy, transparency, and a "bias for action."• Compensation: Competitive base salary + aggressive equity package +performance bonus.• Perks:o Comprehensive Health, Dental, and Vision.o Flexible PTOo $15,000 annual travel credit to take trips on Outdoorsy (Go explore theproduct you protect!).o 401(k) matching.