Lead​/Principal Product Manager, Agents

Help Scout Agent Pillar Leadership

Help Scout builds software for relationship businesses — companies that earn loyalty through outstanding customer service. We've been on this journey since 2011, and today more than 10,000 companies use our platform to support customers of all types, from clients to patients and beyond. Now we're in a new chapter: not only building AI that gives teams more space to focus on the customer experience, but also reimagining how we operate in an AI-native world.

That means shipping and learning faster, without compromising on craft. Great work here carries a strong opinion and sweats the details, regardless of the tools we use to drive it.

We've been a fully remote team since day one, with 120+ teammates now all over the world. It's a culture where you'll be trusted to take ownership, stay curious, and raise the quality of work around you. It comes with clear expectations and a team that will push you to do some of the best work of your career.

If that kind of challenge gives you energy, we'd love to meet you.

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.

The Agents pillar owns all autonomous AI in Help Scout: the unified backend that powers Agent Drafts and AI Answers, Agentic Actions in connected systems, Docs automation, and workflow amplification. It's the most technically complex product area we have, and the most directly tied to how we monetize AI — resolutions, drafts, handoffs, each priced against outcomes rather than seats.

You'll own the vision, roadmap, and execution for this pillar in partnership with engineering, and you'll sit at the intersection of product strategy, monetization design, and customer trust. You'll report to Scott Rocher, our Chief Product Officer.

Note:

This role is open to US-based applicants only.

• 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

• You have shipped AI-powered products and understand how they fail — not…