President of Revenue and Growth

Outdoorsy•Austin, TX

12d

About The Position

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 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 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. 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. 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. 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.

Requirements

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
Thinks in revenue systems, not departments
Comfortable redesigning org structure
Understands capital efficiency at scale
High conviction, relentless
High speed DNA
Deep comfort with data models and instrumentation
Understands AI and ML at practical application level
Can challenge Product credibly and marketing efficacy
Forecast rigor
Global scaling experience
Strong talent magnet - will attract the best
Can replace underperforming VPs quickly - strong bias towards action
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

Responsibilities

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
Implement predictive scoring across lifecycle
AI-driven account and vertical prioritization
Usage-based expansion detection
Automated pipeline diagnostics
Pricing experimentation framework
Evaluate packaging evolution
Introduce usage tiers if relevant
Optimize enterprise bundling and embedding plans
Build monetization experimentation discipline
Improve price realization
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

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.

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