Chief Commercial Officer

Outdoorsy • Austin, TX

14h

About The Position

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.

Nice To Haves

• 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.
• Strategic Leadership & Brand Vision
• 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.
• Growth & Demand Generation
• 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.
• Product Marketing & Communications
• 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.
• You will ensure:
• Clear ICP definition
• Value prop clarity
• Pricing & packaging strategy
• Launch discipline
• Competitive intelligence
• Sales enablement alignment
• Data & Analytics
• 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.
• Brand as a Growth Asset (Not Just Awareness)
• At scale, brand becomes a unit economics lever:
• Lowers CAC
• Improves conversion
• Increases pricing power
• Attracts talent and partners
• You will balance:
• Short-term performance marketing
• Long-term brand equity
• Org Design & Talent
• You will build a team that can scale:
• Performance marketing
• Product marketing
• Brand / comms
• Lifecycle / CRM
• Ops & analytics
• You know when to centralize vs decentralize.
• Cross Functional Leadership:
• As CCO you will be deeply embedded with:
• 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
• External Representation
• Often the public face (or co-face) of the company:
• Press interviews
• Analyst briefings
• Industry events
• Crisis comms
• Partner ecosystems
• You will be credible, disciplined, and consistent.

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