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.

The Ride Platform - Chief AI Growth Officer