Lead Product Manager, Agents

About the role

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. 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.

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 synthe

Benefits

Your Match

How well this role fits your profile.

Company Intel

What employees say

Worked at helpscout? Share your experience