Chief Revenue Officer, AI-Forward

Outdoorsy

CRO leading revenue generation in AI native mobility platform company. Aligns sales, marketing, and customer success for scalable growth.

Posted 5/19/2026full-timeSan Francisco • California • 🇺🇸 United StatesLeadWebsite

Tech Stack

Tools & technologies

Cloud

About the role

Key responsibilities & impact

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

Requirements

What you’ll need

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.
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

Comp & perks

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.

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

data architectureanalytics platformsAI/ML infrastructurecloud data systemsrevenue operationsGTM strategydata analysisautomationM&A integrationinternational expansion

Soft Skills

leadershipcommunicationanalytical capabilitiesoperational capabilitiespresentation skills