Lead Product Manager, Agents

Help Scout • Boston, MA

2d • $172,000 - $198,000 • Remote

About The Position

Help Scout builds software for relationship businesses, helping over 10,000 companies support their customers. The company is entering a new phase, focusing on AI to enhance customer experience and improve operational efficiency. Help Scout operates as a fully remote team with over 120 employees globally, fostering a culture of trust, curiosity, and high-quality work. This role is crucial for the company's growth towards $100M ARR by developing outcome-based products, particularly within the Agent pillar, which focuses on AI-driven support solutions for compliance-driven and trust-cautious businesses.

Requirements

• Shipped AI-powered products and understand how they fail — not just how they work when they work
• Think in outcomes, not features. "Resolutions handled" and "drafts sent" are more interesting than "new settings page launched"
• Strong monetization instincts. Can design a pricing surface that reflects real customer value and explain the tradeoffs when you can't
• 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
• 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
• Genuinely fluent with AI tools and treat them as part of your craft — for research synthesis, strategy testing, rapid prototyping, and customer signal analysis. Have a point of view on where these tools are heading and how they're changing the shape of PM work
• Understand that when execution is cheap, judgment is the bottleneck. Highest-leverage hours are spent on strategy and prioritization — defining what's next and what's not — not on driving the build
• Excellent writer. Help Scout runs on writing, and you make your thinking visible in one-pagers, briefs, and narratives that move decisions forward
• Worked in B2B SaaS and understand the difference between building for support teams vs. building for end consumers

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

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
• Top tier health insurance for you and your dependents (if in the U.S. or Canada)

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed