Chief AI Growth Officer

About The Outdoorsy Group

Founded in 2015, Outdoorsy Group pioneered access to the outdoors by building the world's leading outdoor travel ecosystem. Millions of guests trust Outdoorsy to create lifelong family memories, while hosts rely on its products and innovations to grow their businesses and unlock life-changing sources of income. Outdoorsy Group's portfolio includes Outdoorsy.com, the largest outdoor travel and hospitality marketplace; the Destination Network , a growing collection of campgrounds and glamping retreats set in some of the country's most iconic landscapes; and Roamly , its proprietary insurtech platform powering Outdoorsy.com and enabling insurance infrastructure for global marketplaces. Together, Outdoorsy Group's businesses are united by a long-term mission: to restore our relationship with the outdoors—and with one another.

About Roamly
Roamly is a leading provider of innovative, specialty insurance solutions purpose-built for the modern mobility and marketplace travel economy. As a Lloyd's Coverholder and AI-first insurance innovator, Roamly delivers a robust platform, deep carrier partnerships, and an expanding ecosystem that empowers consumers, professional fleet owners, and marketplaces to unlock new revenue streams while reducing risk. Our technology harnesses AI, advanced automation, and embedded distribution to power tailored coverages for recreational vehicles, carsharing, and other emerging mobility models—covering everything from underwriting and claims to compliance, data analytics, and real-time risk management. Learn more at

Requirements

The Role

The "Why" : We are witnessing the most radical transformation in the automotive industry in a century: the shift from Human-Operated to Software-Defined, Autonomous Mobility. As human behavior expires as the primary variable of risk, Roamly is pivoting to insure autonomous decisions, pricing risk on software quality and sensor fidelity rather than driver history.

The Mission : To lead the largest disruption in the history of insurance by moving from demographic profiling to algorithmic underwriting, effectively "underwriting the code, not the human".

Reporting Structure : This role reports directly to the CEO and works closely with the leadership teams of Outdoorsy, Roamly, and Wheelbase .

Key Responsibilities & Deliverables

• Autonomous Mobility Strategy: Integrate directly with OEM autonomous stacks (Tesla, Rivian, etc.) to access granular driving data and define the technical strategy for the "Robotaxi Use Case"
• Telemetry & Sensor Fusion: Architect high-velocity pipelines to process sensor data (Vision, LIDAR, Radar) and transform raw behavioral data into proprietary "Safety Score" algorithms
• Dynamic Pricing Engine: Develop and lead the "Roamly Autonomy" protocol to adjust premiums in real-time based on software version stability and compute latency
• Agentic AI Deployment: Deploy AI agents at the "Edge" to detect coverage gaps and programmatically negotiate insurance upgrades directly on vehicle infotainment screens
• Team & Collaboration: Lead a lean, high-velocity engineering team to build prototypes and prove concepts that connect the vehicle cloud to the Wheelbase "Mission Control"
• Innovation: Proactively stay ahead of L3-L5 regulatory frameworks (NHTSA/DMV) to ensure the tech stack remains compliant with evolving driverless laws

Key Performance Indicators (KPIs)

• 90-Day Success: Successfully build the "Vehicle to Cloud" (V2C) loop to extract hard telemetry like disengagements and phantom braking from a primary OEM partner
• Ongoing Metric: Reduction in loss ratios through the refinement of algorithmic underwriting based on live vehicle telemetry versus traditional MVR/FICO scores
• Growth Goal: Scale the API-first infrastructure to support seamless switching between personal auto and commercial fleet policies for autonomous fleets

Who You Are (Candidate Profile)

• Required Qualifications: Deep knowledge of ADAS, L3, and L5 autonomy, including an understanding of disengagement reports and operational design domains
• AI-First Technologist: Proven experience with LLMs, Agentic workflows, and Machine Learning; you view AI as the primary interface for software
• IoT & Telemetry Expert: Extensive experience handling time-series data from hardware devices, connected cars, or robotics
• Execution-Minded: You operate with a "Builder's Mindset," preferring prototypes over PowerPoints and possessing an impatient bias for action
• Austin-Centric: (Preferred) Deeply plugged into the Austin tech scene and its ecosystem of robotics and autonomous manufacturing
• Technical Proficiency: Expert in 5G/MQTT/Starlink connectivity layers and architecting data pipelines for high-frequency telemetry

Benefits

Why You'll Love Working Here

• Competitive Compensation: Competitive base salary commensurate with experience
• Growth Opportunity: Architect a world-first protocol for the largest disruption in the history of insurance
• Ground Zero of Autonomy: Work from our Austin HQ, the global hub of the autonomous revolution
• Comprehensive Benefits: 100% paid medical and flexible PTO (standard Outdoorsy Group benefits)
• Work-Life Balance: RV rental discounts and a culture that values the outdoor lifestyle we enable