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Help Scout is seeking a Head of Product for its Conversations product group, which encompasses Inbox (the core workspace where support teams manage all customer interactions across channels) and Copilot (AI-powered assistance that helps agents work faster and smarter). You'll own this group end-to-end: vision, strategy, roadmap, monetization, and revenue accountability. You report to the Chief Product Officer and will drive hands-on product strategy while building and managing a growing PM team.
Key responsibilities include: setting vision for how Inbox and Copilot evolve as an integrated experience; owning the Inbox roadmap with focus on speed, reliability, and polish as differentiators; driving Copilot roadmap including integrations, contextual summaries, and in-the-moment assistance; designing monetization strategy across seats and AI usage; partnering deeply with the Autonomy (agent automation) product group to ensure seamless integration; spending significant time with customers to understand support workflows and where AI adds value; collaborating with GTM and Customer Success on adoption and feedback loops; and building out the Conversations PM team with strong coaching and craft standards.
Help Scout has been fully remote since 2011 and now has 120+ employees globally. The company serves 10,000+ businesses with 3+ billion conversations processed annually. The Conversations group is the most-used surface in the product—where every user spends most of their day—making it critical to the business and the foundation for future platform expansion.
You should have experience owning core products at scale that people use daily, with fluency in both product features/UX and commercial strategy. You've shipped AI-powered products and understand their success patterns. You excel at cross-functional collaboration, think in outcomes (time to resolution, efficiency gains), care deeply about craft and polish, have strong monetization instincts, and have managed product managers while still enjoying hands-on work. You're data self-sufficient and use analytics to drive decisions.
