Senior Product Manager - AI Enablement

Tremendous is the global platform built for businesses to send thousands of payouts to anyone, anywhere, for free. We're trusted by 20,000 organizations like Atlassian, MIT, and United Way to deliver gift cards and money to millions of recipients worldwide. Our customers (researchers, marketers, HR teams, nonprofits, and platform businesses) rave about how fast and easy Tremendous is to use. Check out our ratings on G2. Tremendous is profitable and growing without outside investors. We’re a fully remote, high-documentation, low-meeting culture, which means more time for what matters in both your professional and personal life. The team agrees– our employee NPS is in the high 80s. About the role We're hiring a Senior Product Manager for our AI Enablement team. This team has one mission: make everyone at Tremendous faster by making AI accessible, reliable, and secure across the company. It builds Rockie (our internal AI agent that debugs issues, runs data analyses, and writes code), internal automations for teams like finance and support, and the infrastructure that makes AI safe to use company-wide. This is not a typical PM role. You'll own the internal AI product surface end to end: finding the workflows worth automating, mapping how they actually work, and turning them into working prototypes that our engineers then build into production systems. You'll report to our co-founder / Head of Product and work with a team of fast-moving engineers. You will Run discovery across the whole company. Sit with finance, sales, support, and ops. Map their workflows. Find the automations and agents worth building, and prioritize by business impact. Prototype the v1 yourself. You'll build working versions of agents and automations with AI tools (Claude, Cursor, agent frameworks), because a working prototype is the best requirements doc. Turn prototypes into specs engineers can build from. You keep a pipeline of well-defined, shovel-ready work so the team always knows what to build next and why. Own quality. Define what "working correctly" means for each automation: evals, guardrails, edge cases, and observability. Keep the team shipping. You'll do the PM work too: clear blockers, make scope calls, and keep projects moving through the build phase. Drive adoption. An automation nobody uses is a failed project. You'll roll out what we build and iterate with the teams whose work changes. Set the vision and roadmap. Define where Rockie and our internal agents go as internal AI grows from a team into a platform. You have Professional software engineering experience. You've built and shipped production software, and you understand the security risks that come with giving AI systems access to real data and tools. Experience owning a product end to end: as a technical founder, founding engineer, forward-deployed engineer, or PM. Formal PM experience is a nice to have, not a requirement. Deep, hands-on AI experience. You've shipped LLM-powered systems and you build with AI tools daily. You understand agents, evals, and where models fail. Business sense. You can sit with a finance or sales team, understand their process, and spot what's automatable (and what isn't). A 0-to-1 track record. You've built products or tools from nothing. Outstanding written communication. We're a documentation-first culture. What's cool about the role The work itself. You'll spend your days building agents and automations with cutting-edge AI tools, at a company that's fully bought in on AI. Competitive pay and equity. Base salary for this role: $225,000 to $300,000. Real benefits. 100% covered health (US), unlimited PTO, 12-16 weeks paid parental leave. Fully remote. Work from anywhere in the Americas. Great culture. Read more about how we work in our public handbook.