Staff Product Manager, AI Platform

About This Role

You will be Headway's first AI Platform product manager. Your mission: build the AI platform that makes every Headwegian an AI-native employee.

In Q1 2026, we launched Eddy — an internal AI assistant with direct access to Snowflake, Jira, Slack, GitHub, Google Workspace, and more. Early adoption is strong in R&D, but usage drops off sharply outside of it. Eddy is the first of what we believe will be many: an ecosystem of agents, skills, evals, and data integrations that together become Headway's AI platform layer. You'll own that vision — and the roadmap to get there.

This is not a classic internal tools role. You are a product builder with deep AI fluency who will ship fast, write evals, configure agents, and sit with CX, Ops, Sales, Finance, and Clinical teams to find the workflows where AI actually moves the needle. Today, three engineers are building Eddy without a PM. You'll be the first, building the vision that the team is currently shipping without.

You Will

• Set & build the AI platform vision. Define what Headway’s agent harness should look like — from platform & data architecture to the connected ecosystem of agents, skills, and integrations that will sit on top of it.
• Own Eddy's roadmap. Replace real-time feature triage with a first-principles product strategy. Build the user research pipeline, the eval infrastructure, and the prioritization framework that don't exist today.
• Enable adoption across functions. Partner with functional leaders in CX, Ops, Sales, Finance, Clinical, and more to identify high-value AI workflows, build them, and turn non-adopters into power users.

Who You Are

• 8+ years of product experience, with at least 2 years shipping AI or AI-adjacent products.
• You have personally built or configured AI agents, skills, or workflows — not just managed the engineers who did. You write prompts, design evals, and know where LLMs break.
• Strong AI fluency: prompt engineering, context management, RAG, tool use, evals. You can hold your own with ML engineers and have real opinions on cost/latency/quality tradeoffs.
• A platform thinker who can build for other builders, not only end users.
• A cross-functional operator who translates AI capabilities into business value for non-technical stakeholders — and knows how to say "no" to low-value requests without losing the relationship.
• Ruthlessly prioritized. You can hold a product roadmap, a platform roadmap, and an adoption strategy in your head at once and know which to pull on this week.
• Above all, you believe AI is going to fundamentally change how knowledge workers operate — and you want to prove it at a company where the CEO agrees with you.

We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.

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