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

Mission

Architect and lead the next-generation AI-native revenue platform that scales the

company to $1B+ ARR while increasing NRR, revenue per employee, and operating

leverage.

This executive will unify Product, Marketing, Sales, Customer Success, Retention, and

RevOps into a data-driven growth system.

Reports to: CEO

Owns: Marketing, Sales, Customer Success, RevOps, Growth, Pricing & Packaging

Build: a repeatable, scalable growth engine that aligns product, brand, and revenue —

keeping integrity of unit economics

Board exposure: High

Cross Functional Leadership:

You will be deeply embedded with:

• CEO – narrative, strategy, external messaging

• CRO / Sales – pipeline, conversion, enablement

• CMO and Growth – viral loops, network effects, retention, growth in new Geos

• Product – roadmap influence, GTM timing

• Finance – budgeting, ROI, efficiency

Legal / Comms – risk, disclosures, crisis response

External Representation

Often a key public face (or co-face) of the company:

• Press interviews

• Analyst briefings

• Industry events

• Crisis comms

• Partner ecosystems

Org Design & Talent

You will build a team that can scale:

• Performance and Growth

• Product marketing

• Brand / comms

• Lifecycle / CRM

• Ops & analytics

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

1. Revenue Architecture

• Redesign GTM model for $1B scale

• Clarify segmentation (enterprise, mid-market, self-serve)

• Implement verticalized pods

• Align product usage signals to expansion plays

• Optimize land-and-expand mechanics

Must think like:

A systems engineer of revenue and a high performance CMO have collided

2. AI-Native Revenue Intelligence

• Implement predictive scoring across lifecycle

• AI-driven account and vertical prioritization

• Usage-based expansion detection

• Automated pipeline diagnostics

• Pricing experimentation framework

This role should make our revenue engine look more like a data platform than a sales

org.

3. Pricing & Monetization Strategy

• Evaluate packaging evolution

• Introduce usage tiers if relevant

• Optimize enterprise bundling and embedding plans

• Build monetization experimentation discipline

• Improve price realization

At $500M, pricing becomes a key and primary growth lever.

4. Organizational Design

• Rationalize Marketing and global GTM structure

• Clarify role specialization

• Increase productivity per person and deliver high self-serve model in the

business - Roamly Wheelbase Myles

• Reduce friction between Sales and CS

• Strengthen RevOps as a power center

The goal:

Higher leverage, not more headcount.

Experience

• Scaled a technical, data-heavy platform from ~$300–500M to $1B+

• Operated in hybrid PLG + enterprise model

• Led global GTM teams (Americas, EMEA, APAC)

• Owned or redesigned pricing at scale

Skill Profile

Strategic

• Thinks in revenue systems, not departments

• Comfortable redesigning org structure

• Understands capital efficiency at scale

• High conviction, relentless

• High speed DNA

Technical Fluency

• Deep comfort with data models and instrumentation

• Understands AI and ML at practical application level

• Can challenge Product credibly and marketing efficacy

Operational

• Forecast rigor

• Global scaling experience

• Strong talent magnet - will attract the best

• Can replace underperforming VPs quickly - strong bias towards action

Cultural

• Founder mindset - Hardcore, Bias toward action – incites actions from others

• A Leader – people rally around this person and the dictates

• Direct, analytical

• Board and Analyst -ready communicator (Wall St comfortable)

• Resilient under scale complexity

• Strong energy

• Comfortable making structural changes

What This Person Is Not

• Not just a headcount-scaling CRO

• Not a brand-only CMO

• Not a founder-type visionary without scaling discipline

• Not a legacy enterprise sales executive from non-technical environments

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.

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.