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.

What You Will Do

Build a repeatable, scalable growth engine that aligns product, brand, and revenue — without

breaking unit economics.

1. Strategic Leadership & Brand Vision

• Market positioning and differentiation

• Category creation or category leadership strategy

• Core messaging architecture

• Executive narrative for:

o Investors

o Customers

o Press

o 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.

2. 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.

3. 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

4. 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.

5. 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

6. 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.

7. 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

8. 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.

Who You Are

• 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.

Why Join?

• We are attacking an $11 Trillion dollar total addressable market. We will

have product $4 Billion in total sales by May of 2026 and growing fast. The

company has been profitable for the last 3 years and will achieved it’s 4th year of

profitability in 2026.

• Impact: You are not just selling; you are helping professionals create wealth by

renting their assets and helping consumers and travelers explore the world

safely. You are passionate about the mobility markets and especially the

autonomous revolution.

• Culture: We are a team of road-trippers, campers, and builders. We value

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 PTO

o $15,000 annual travel credit to take trips on Outdoorsy (Go explore the

product you protect!).

o 401(k) matching.