Staff Product Manager, AI Platform

About the 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.

Responsibilities

• 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.

Requirements

• 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.

Qualifications

• 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.

Skills

• Product management
• AI fluency
• Platform thinking
• Collaboration and cross-functional leadership

Benefits

• Competitive compensation package
• Flexible work arrangements
• Professional development opportunities
• Health and wellness programs

Pay

Competitive compensation package

Schedule

Flexible work arrangements

Company Information

Headway is a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.). We are committed to the full inclusion of all qualified individuals and participate in E-Verify.