Chief AI Growth Officer

Position Summary

The Chief AI Growth Officer (CAIGO) is responsible for driving the execution of the company's strategy through the application of artificial intelligence across product, marketing, customer acquisition, channel expansion, revenue generation, retention, operations, product innovation, and automation. The role is responsible for architecting, building and leading AI-driven business acceleration across all functions. The company operates an AI native mobility platform with a marketplace for recreational and travel assets, called “Outdoorsy”, a marketplace for Autos, EVs and AVs called “Ride”, an AI insurance platform marketed under the brand “Roamly”, and a vertically integrated SaaS mobility management system called “Wheelbase” and an AI innovation lab called “Roamly Labs”. 

This executive combines the responsibilities of customer acquisition, growth leadership, AI transformation, product strategy, and operational scaling. The role sits at the intersection of revenue, data, marketing, product, sales, engineering, and customer experience.

The CAIGO reports to the CEO and partners with the executive leadership team to build, and operationalize AI-native growth systems that create a durable competitive advantage.

Hybrid/Onsite in Austin, Texas or Bay Area, CA (preferred)

Requirements

Core Responsibilities:

AI-Driven Growth Strategy

• Develop and execute the company’s AI-powered growth strategy.
• Create opportunities where AI can improve:
• Customer acquisition
• Conversion rates
• Retention
• Marketplace liquidity
• Pricing optimization
• Sales productivity
• Operational efficiency
• Embedding and distribution
• Opening of new channels
• Build scalable AI-enabled growth loops across the organization.

Revenue & Go-to-Market Optimization

• Apply AI to improve:
• Demand generation
• Personalization
• Lead scoring
• Sales automation
• Customer segmentation
• Dynamic pricing
• Revenue forecasting
• Oversee AI-enhanced growth channels, including:
• Lifecycle marketing
• SEO/content automation
• Paid acquisition optimization
• Conversational commerce
• AI agents for sales and support

AI Product & Platform Innovation

• Partner with Product and Engineering to launch AI-native experiences.
• Drive development of:
• Recommendation systems
• Predictive analytics
• AI copilots
• Voice and conversational interfaces
• Autonomous workflow systems
• Marketplace intelligence tools
• Evaluate emerging AI technologies and vendor ecosystems.

Data & Experimentation

• Build a rigorous culture of experimentation using Agentic systems and tools.
• Establish metrics and KPI frameworks for:
• Growth efficiency
• Model performance
• Acquisition and channel optimization
• Embedding, Retention and LTV
• AI adoption across all functions
• Leverage first-party data to create defensible growth advantages.

Operational Automation

• Identify opportunities to reduce operational costs through AI automation.
• Implement AI systems across:
• Customer acquisition growth throughout marketing operations
• Internal productivity
• Customer support
• Claims and underwriting workflows
• Finance and reporting
• Drive organizational productivity improvements using Agentic systems

Cross-Functional Leadership

• Align Growth, Product, Data, Engineering, Marketing, and Operations teams around AI initiatives.
• Create governance frameworks for responsible AI deployment.
• Train and lead executives and the board on AI strategy and competitive implications.

Key Metrics Owned

• Customer acquisition and retention
• Channels, partnerships and embedding distribution 
• AI-driven Cost Savings
• Automation Efficiency Gains
• AI Native Product development 
• Marketing Efficiency Ratio (MER)
• Marketplace Liquidity Metrics
• Experiment Velocity
• Forecast Accuracy

Qualifications:

• 4+ years in growth, product, AI, marketplace, or digital transformation leadership roles.
• Demonstrated experience scaling high-growth technology businesses.
• Deep understanding of:
• Generative AI
• Machine learning systems
• AI agents and automation
• Growth marketing
• Data analytics
• Marketplace dynamics
• Experience leading growth functions and teams.
• Hard-core operational and analytical rigor.
• Ability to communicate technical AI concepts to non-technical stakeholders.

Preferred Background

• Agentic systems, Marketplace, SaaS, fintech, mobility, travel, or insurtech experience
• Experience implementing AI at enterprise scale
• Familiarity with:
• LLM infrastructure
• Agentic workflows
• Vector databases
• Growth automation platforms
• Data warehouses and BI tools

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: (Standard Outdoorsy Group benefits apply, including 100% paid medical and flexible PTO).
• Work-Life Balance: Enjoy RV rental discounts and a culture that values the very outdoor lifestyle we enable.