Lead revenue growth initiatives through a data-driven approach, transforming the marketing strategy to scale Roamly's AI-driven insurance offerings in the mobility sector.
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.
Requirements
Outcomes (First 12 Months)
1. Increase Net Revenue Retention to elite tier (120–130%+ depending on model)
2. Expand enterprise ACV and strategic account penetration and Myles embedding
3. Reduce CAC payback while improving growth rate
4. Increase revenue per GTM employee
5. Install AI-native revenue intelligence layer
6. Improve pipeline velocity
7. Tighten Product ↔ GTM feedback loop
Core Mandate Areas
First 180-Day Plan
First 30 Days
• Deep segmentation & revenue diagnostics
• Org capability assessment
• Pipeline health and expansion analysis
• Pricing architecture review
• Identify top 10 structural bottlenecks
31 - 90 Days
• Announce org refinements
• Install revenue intelligence roadmap
• Launch vertical pod pilots
• Redesign expansion plays
• Implement AI-assisted account prioritization
90 - 120 Days
• Pricing adjustments or packaging evolution
• Improve forecast accuracy materially
• Early lift in expansion metrics
• Increase pipeline velocity
• Replace 1–2 key leadership gaps if necessary
This role should feel like a pre-IPO platform builder.
Who you are:
- Proven track record scaling a technical, data-intensive platform from ~$300–500M to $1B+ in revenue, driving durable, multi-year growth.
- Experience operating and optimizing a hybrid PLG + enterprise GTM model, aligning self-serve, expansion, and field sales into a cohesive revenue system.
- Led and scaled global GTM organizations across Americas, EMEA, and APAC, with demonstrated success managing regional complexity and performance.
- Owned or fundamentally redesigned pricing and packaging at scale, including deep exposure to usage-based and consumption-driven monetization models.
- Demonstrated ability to think in end-to-end revenue systems—not functional silos—redesigning org structures, incentives, and workflows for leverage and capital efficiency.
- Strong technical fluency with data models, instrumentation, and analytics; practical working knowledge of AI/ML applications in revenue forecasting, segmentation, and prioritization.
- Credible partner to Product and Marketing leadership, able to challenge roadmaps, growth assumptions, and performance efficacy with data-driven rigor.
- Operationally disciplined leader with forecast accuracy, pipeline governance, and repeatable global scaling playbooks.
- Proven talent magnet who attracts high-caliber leaders, decisively addresses underperformance, and upgrades teams quickly with a strong bias toward action.
- Founder-minded executive with high conviction and resilience, known for direct, analytical communication, board and analyst readiness, and the ability to lead structural change under scale complexity.
Benefits
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.
Health Insurance
Comprehensive Health, Dental, and Vision.
Other Benefit
401(k) matching.
Paid Time Off
Flexible PTO
Outdoorsy builds an expansive outdoor travel ecosystem, offering the world's largest RV rental marketplace. It's designed for outdoor enthusiasts seeking accessible and enriching travel experiences while connecting them with nature and each other.
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