The Ride Platform - Growth AI Systems Lead

About The Ride Platform

The Ride Platform, Inc. is the parent company of Outdoorsy, Ride, Wheelbase, and Roamly. We are named for the single transaction where an operator meets a renter. We build end-to-end for the Operator Economy: the marketplaces to book (Outdoorsy, Ride), the enterprise SaaS to manage (Wheelbase), and the insurtech (Roamly) to protect the assets people turn into businesses. We enable millions of people to explore the world while helping independent operators build generational wealth. Our mission is to build the essential infrastructure for the mobility economy.

About the Role

You will build the AI operating foundation. This includes workflows, agents, tooling, governance, and self-serve infrastructure. Your goal is to help every marketer and agent work AI-first by default. We need this done safely, efficiently, and across an ecosystem of different businesses running on one shared platform.

The mandate is marketing-first and designed for reuse. You will prove the pattern in marketing, then templatize it outward to sales, retention, and the rest of the portfolio. You will build this framework alongside the Head of Growth & Systems. We want it validated against how our team actually works, rather than a top-down ideal. Success is measured by voluntary adoption; if the framework requires heavy enforcement, it is likely too high-friction. You will start as a pod-of-one with a path to a small team.

Requirements

Key Responsibilities & Deliverables

• AI Framework & Standards: Establish how the team uses AI. You will define model selection per task (balancing cost and quality), create prompt and agent patterns, and build a standardized, shared-context repository structure.
• Portfolio & Brand Flex: Build a modular context architecture. One platform must serve Outdoorsy's consumer warmth, Ride's fleet-operator pitch, Wheelbase's B2B voice, and Roamly's regulated insurance tone. You will manage shared rails with per-brand context.
• IC Workflows & The Agent/Skill Library: Develop reusable skills, agents, and scripts. Your goal is to turn one-off hacks into shared, documented tooling.
• Self-Serve, Governed Infrastructure: Create a secrets vault, scoped service accounts, and reusable integration scripts. This ensures people and agents are not blocked by access issues. We prioritize self-serve and governed access over key-sharing.
• Governance, Risk & Compliance: Define what data (PII, insurance, payment) can be sent to which model. You will manage audit logging of agent actions in production, implement human-in-the-loop checkpoints, and oversee AI-generated-content compliance. Note that Roamly is regulated, so state insurance advertising rules apply regardless of who or what wrote the copy.
• Evals, Observability & Cost: Implement regression and eval harnesses to ensure we measure agent output quality rather than assuming it. You will manage the tracing of agent actions and provide per-team and per-workflow cost and token attribution.
• The Context Substrate: Maintain the shared, regenerating "team memory" layer that both humans and agents can read from and write to.

Who You Are (Candidate Profile)

• You build like a product engineer. You ship tools, agents, and infrastructure instead of just creating slideware.
• You are AI-native. You are fluent in agent frameworks, MCP, tooling, model tradeoffs, evals, and prompt engineering.
• You have strong instincts for security and governance. You treat data handling and audit as requirements, not afterthoughts.
• You understand marketing workflows or can learn them quickly. You build for the team’s actual needs.
• You are comfortable spanning B2C marketplaces, B2B SaaS, and regulated insurtech motions. If you have not done all three, you can demonstrate that you learn new business models quickly.
• You excel at enablement and change management. This includes documentation, training, and bringing skeptics along with the new process.
• You act as a player-coach who is comfortable starting as a pod-of-one while planning for a small team.

Nice-to-Haves

• Your background might include experience as a Forward Deployed or Solutions Engineer at a technical or fintech company. You might be a RevOps or MarTech professional who writes code, a marketing technologist, or someone who has built GTM tooling.
• Experience in fintech or a regulated industry (e.g., Stripe, Ramp, Brex) is a plus, as it indicates the data-governance instinct this role requires. You are likely fluent in tools like Clay, n8n, and Python.

Benefits

What We Offer

• Competitive Compensation: Base salary DOE.
• Growth Opportunity: Join a company in its early stages and help build its success from the ground up.
• Equity: Opportunity to earn equity compensation.
• Comprehensive Benefits: 100% company-paid medical premiums for employees, 401(k) match, and Flexible PTO.
• Vibrant Culture: Work at our Austin HQ with catered lunches, happy hours, and team-building events.
• Work-Life Balance: We offer marketplace discounts and maintain a culture that values the balance between work and adventure.