AI-Forward Chief Revenue Officer (CRO)

Position Summary

The Chief Revenue Officer (CRO) is an AI native executive who is responsible for all revenue-generating functions across the company, including sales, partnerships, customer success, revenue operations, pricing strategy, and product unit economics. 

The CRO aligns marketing, sales, pricing, customer retention, and expansion efforts to accelerate predictable and scalable growth. 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”. 

The CRO reports directly to the CEO and partners closely with product, finance, data and analytics, operations, and marketing leadership.

Location - Austin or Silicon Valley (preferred).

Requirements

Qualifications

Revenue Strategy & Growth

• Develop and execute the company’s overall revenue strategy.
• Drive pricing strategy and go-to-market execution of product and service economics.
• Drive ARR, bookings, gross profit, and net revenue retention growth.
• Own and drive Marketplace Liquidity Metrics.
• Build scalable go-to-market systems for enterprise, SMB, marketplace, and consumer segments.
• Identify new revenue streams, pricing opportunities, and expansion channels.
• Lead Agentic AI systems to be leveraged across the business.
• Build automation using Agentic systems to expand distribution and reach of the company’s products and services.

Commercial Leadership

• Lead Commercial activities including:
• • Sales
  • Partnerships & Alliances
  • Channel and Embedding Sales
  • Account Management and Retention
    
• Establish revenue and unit economics forecasting discipline and pipeline management.
• Design quota structures.

Customer Success & Retention

• Set goals and targets and lead execution around customer retention, expansion, and account health.
• Improve ARR, NRR, churn reduction, upsell, and cross-sell initiatives.
• Build scalable customer lifecycle programs.

Revenue Operations

• Oversee RevOps, including:
• • CRM infrastructure
  • Pipeline analytics
  • Geographical planning
  • Sales enablement
  • Revenue forecasting
• Organize and define  KPI dashboards and lead operational rigor.

Cross-Functional Leadership

• Partner with Marketing on demand generation and CAC efficiency.
• Partner with Product on pricing, subscriptions, monetization and customer feedback loops.
• Partner with Finance on forecasting, board reporting, and growth planning.

Key Metrics Owned

• AI and Automation Metrics
• AI Model Performance
• ARR / MRR
• Product and Service Pricing
• Bookings
• Pipeline Coverage
• CAC Strategies 
• LTV/CAC
• Net Revenue Retention (NRR)
• Gross Revenue Retention (GRR)
• Churn
• Sales Efficiency
• Average Contract Value (ACV)
• Revenue Growth Rate

• Data Quality Scores
• Dashboard Adoption
• Analytics Utilization
• Operational Efficiency Gains
• Forecast Accuracy
• Customer Insight Effectiveness

• Cohorted liquidity by geography
• Repeat liquidity behavior
• Supply-side earnings concentration
• Time-to-book trends
• Conversion by category
• Supply utilization curves
• Organic vs paid demand efficiency
• Insurance or trust-related friction metrics
• Loss and Expense ratios by cohort
• Combined ratio
• Policy in force and policy retention
• Risk retention strategy
• AI Bind Rate
• Claims Automation Rate
• Embedded Insurance Attach Rate
• Take rate + insurance margin

Preferred Background

• Marketplace, mobility, fintech, or insurtech experience
• AI-native platform development
• Experience building centralized data organizations
• Familiarity with modern stacks: Claude, Gemini/Vertex; Databricks; BigQuery; AWS/GCP/Azure; dbt; Looker/Tableau; Vector databases and LLM infrastructure

Qualifications

• 5–8+ years leading revenue operations in hyper-growth technology marketplace and fintech companies.
• Experience scaling revenue from early stage through growth stage or public company environments.
• Deep expertise in:
• • Data architecture
  • Analytics platforms
  • AI/ML infrastructure
  • Cloud data systems
• Experience managing enterprise-scale data organizations.
• Strong understanding of marketplaces, SaaS, AI-first fintech, insurtech, and consumer internet metrics.
• Demonstrated success managing fast-paced GTM organizations.
• Deep analytical and operational capabilities.
• Ability to communicate complex data concepts to executive leadership.
• Experience presenting to boards and investors.

Preferred Background

• Online Marketplace, Fintech or vertical SaaS experience
• AI-driven growth or automation experience
• Experience with complex regulated industries (insurance, mobility, fintech)
• M&A integration or international expansion experience

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.