AI Product Manager

The Opportunity

Product management on this team isn't coordination work. It's co-building the product with engineering.

We're looking for a Product Manager to embed in a core PI2 product and engineering team and own the product surface at the intersection of behavioral science, enterprise workflow, and AI. You'll pair tightly with engineers moving fast, make decisions without waiting for permission, and use AI as a core instrument of your craft — not a side capability. You'll define what we build, why we build it, and how we know it worked.

But the role goes further. PI2 is evolving toward AI-delivered experiences that go well beyond a traditional UI; ambient, agentic, and API-first surfaces that meet users where they already work. You'll shape that evolution: defining the product model, designing for partners and integrations, and owning the outcomes that prove PI's value inside and outside the walls of our existing products.

The AI landscape is moving fast. We don't expect you to arrive with every answer, but we expect you to be the kind of person who figures it out, stays curious, and learns faster than the pace of change. If you're a self-starter who thrives in ambiguity and gets energized by hard problems, this role was built for you.

What you’ll do

• Own the product strategy and roadmap for PI’s AI surface, Obi, and the AI-powered workflows built alongside it, with real accountability for response quality, user trust, and measurable outcomes across all of it.
• Define and maintain the evaluation framework that tells the team whether Obi and its adjacent workflows are working: rubrics, test cases, quality signals, and the instrumentation to track them over time.
• Pair directly with engineers in tight delivery cycles, providing the clarity they need to move fast without waiting on meetings or approvals. Provide the deep details, including deep details on AI evals, prompt architecture, and system-prompt design.
• Operate with high autonomy on day-to-day decisions while staying closely connected to business objectives; you'll be trusted to make the call, not wait for one.
• Run continuous discovery to stay close to customer reality; interviews, opportunity mapping, synthesis of product and behavioral signal; ensuring that roadmap decisions are grounded in evidence, not assumptions.
• Design AI-powered features and workflows with a clear point of view on what AI should and shouldn't do in each context and the intellectual curiosity to keep learning as the technology evolves.
• Pair with a data scientist to build the instrumentation and outcome tracking that tells the team what's working: adoption signals, time-to-value metrics, and experimentation results.
• Translate ambiguous strategic questions ("should this be a feature or an integration?", “when is this response good enough?”, "when is the UI a scaffold and when is it a ceiling?") into clear decisions the team can execute against.
• Document as you execute; write the PRDs, eval specs, JIRA artifacts, and decision memos.

What you bring

If you’ve got all of the below, drop what you’re doing and apply. If you’ve got most of it, we still want to hear from you.

• 5-8 years of product management experience with a track record of shipping, not just planning, especially shipping AI. You've owned features from discovery through delivery and have the outcomes to show for it.
• Passion for using AI in every aspect of your work. We're an AI-forward team that expects every member to take full advantage of modern tools to sharpen thinking, move faster, and extend the team's capacity.
• A self-directed learning orientation. AI is evolving fast, and you're the kind of person who stays ahead of it, experiments with new tools, and brings what you learn back to the team.
• A demonstrated ability to work through ambiguity. You don't need every answer handed to you; you ask good questions, form a hypothesis, and move forward.
• Strong research instincts, experience running customer discovery, and judgment on when to move and when to keep discovering. You can design and run interviews, synthesize signals, and translate what you learn into product decisions. You do discovery, you don't just consume it. 
• A collaborative team player who can operate independently from day-to-day leadership direction but works closely and generously within their immediate team; engineers, designers, and scientists who are building alongside you.
• The ability to write with the clarity that replaces meetings. Your PRDs, decision memos, and Slack updates are crisp, decisive, and make the tradeoffs visible.
• Experience working directly with engineers in fast-moving delivery cycles. You're the kind of PM engineers want to build with, not around.
• A builder's mindset. You take ownership, drive clarity, and cover surface area beyond your title when the work calls for it.

Nice to have

• An engineering background or technical foundation; you don't need to write production code, but understanding how software is built makes you a better partner to the engineers building it.
• Experience with AI concepts (i.e., LLMs, agents, APIs, MCP), even if you're still building fluency. Curiosity and a learning track record matter more than credentials here.
• A Continuous Discovery practice (Teresa Torres-style). You can run your own customer interviews and extract opportunity signal, not just consume research reports someone else produced.
• B2B enterprise SaaS background, especially in HR tech, talent, workforce, and behavioral assessments platforms.
• Prompt engineering fluency. You can prototype and evaluate AI behavior yourself, not just describe what you want to an engineer.

What it’s like here

You’ll be embedded in a core Product team building on a 70-year-old science foundation, with the scale of an established platform and the pace of a company still very much in growth mode. You’ll work shoulder-to-shoulder with Product, Engineering, Design, and Behavioral Science — and your work will be visible all the way up to the executive team and, through our published insights, to the broader world of work.

PI is headquartered in Westwood, MA, and is fully remote with options for working in the office with quarterly team onsites at the office. This is an exempt, salaried position ($180,000 - $215,000) with full access to PI’s benefits package, including unlimited PTO and 401(k).