Lead Product Manager

Role Description

Help Scout has earned something most software companies never get: genuine trust. 10,000+ businesses use us because we've always believed that customer relationships are the business — and that every interaction, no matter who or what handles it, should feel like it came from someone who cares. That trust took a decade to build. Now it's the foundation for something bigger.

The support industry is changing shape. AI will handle more of what support teams used to do. Seat revenue will compress. That's not a threat to manage — it's the condition we're designing for. Our path to $100M ARR runs through outcome-based products: resolutions handled, drafts sent, actions taken on behalf of a customer. The Agent pillar is how we get there.

But here's what makes Help Scout's version different: our customers are compliance-driven, trust-cautious, and deeply invested in how their customers feel. They're not looking for AI that moves fast and breaks things. They need AI that earns its place — one step at a time, with evidence. The trust ladder we're building — from assisted drafts to autonomous answers to agentic actions — is a product philosophy as much as a roadmap. Your job is to make every rung feel inevitable.

What You'll Do

• 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.

Qualifications

• 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.

Benefits

• Competitive salary and an internal, transparent salary formula based on market data.
• Flexible time off – you choose the holidays and vacations that make sense for you.
• 12 weeks of fully paid parental leave for all new parents, including adoption and foster care.
• A home office stipend to help you get set up and productive.
• A co-working stipend up to $300 a month if you choose to work out of your house.
• A yearly professional development stipend of $1,800 to help you grow in your craft.
• If you’re in the U.S. or Canada, we offer top tier health insurance for you and your dependents.