Lead Product Manager, Agents

Help Scout builds software for relationship businesses, and they are seeking a Lead Product Manager for their Agents pillar. This role involves owning the vision, roadmap, and execution for AI-powered products, focusing on customer trust and monetization strategies.

Responsibilities:

• Own the full product roadmap for the Agent pillar — unified Agent backend, Agent Drafts, AI Answers, Agentic Actions, Docs automation, and workflow amplification
• Drive the consolidation of Drafts and AI Answers onto a single backend system, enabling the full Agent capability set to compound from a shared foundation
• Define the experience and configuration UX that moves customers up the trust ladder — from "let me review that draft" to "handle it without me"
• Shape how the Agent monetizes: resolutions, drafts, handoffs, and docs improvements are all outcome-priced surfaces; you'll own the logic for how customers experience and pay for each
• Partner closely with the Intelligence and Conversations PMs — Agent needs signals from Intelligence and coordination with Conversations to work as a coherent system, not a feature stack
• Spend real time with customers: understanding where they trust the AI, where they don't, and what would move them
• Work with GTM and CS to ensure the Agent story is clear, the adoption motion is tight, and customer feedback loops back into the roadmap

Requirements:

• You have shipped AI-powered products and understand how they fail — not just how they work when they work
• You think in outcomes, not features. 'Resolutions handled' and 'drafts sent' are more interesting to you than 'new settings page launched'
• You have strong monetization instincts. You can design a pricing surface that reflects real customer value and explain the tradeoffs when you can't
• You're technically fluent enough to build genuine trust with engineers — you don't need to write the code, but you can hold a meaningful conversation about system architecture and make better decisions because of it
• You know how to move customers along a trust curve: what confidence signals matter, how to sequence capability rollout, and when to hold back a feature because the experience isn't ready yet
• You're genuinely fluent with AI tools and treat them as part of your craft — for research synthesis, strategy testing, rapid prototyping, and customer signal analysis. You have a point of view on where these tools are heading and how they're changing the shape of PM work
• You understand that when execution is cheap, judgment is the bottleneck. Your highest-leverage hours are spent on strategy and prioritization — defining what's next and what's not — not on driving the build
• You're an excellent writer. Help Scout runs on writing, and you make your thinking visible in one-pagers, briefs, and narratives that move decisions forward
• You've worked in B2B SaaS and understand the difference between building for support teams vs. building for end consumers