Head of Product, Conversations

Who we areHelp Scout started in 2011 with a simple premise: support software should treat customers like people, not tickets. 3+ billion conversations later, more than 10,000 companies use Help Scout to grow relationships with 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.

Your impactHelp 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 should feel like it came from someone who cares. That trust took a decade to build, and now it's the foundation for something bigger.

The support industry is changing shape. AI will take on more of the tedious work so humans can lean into the relationship part. At Help Scout, the place where that relationship actually happens is the Conversations product group, which spans two product lines. Inbox is the workspace: every channel and every conversation in one place, built for the people who spend their whole day inside it. Copilot is AI working alongside them: drafts ready to review, context at their fingertips, and the tedious parts handled so every reply is faster and better.

Conversations is the most-used surface we have. This is where every user spends most of their day, so speed, reliability, and craft are the product. It's also where the rest of the platform becomes real: Agent hands conversations to humans at the right moment, customer context shows up right where the work happens, and every one of those moments either builds trust or spends it. You'll be accountable for bringing it all to life with clarity and impact.

About the roleYou'll own the Conversations product group end to end: vision, roadmap, monetization, and results for the Inbox and Copilot product lines. You'll report to Scott Rocher, our Chief Product Officer, and you'll be accountable for the revenue growth of the group. This is a player/coach role.

Inbox and Copilot are the surfaces our customers touch most, the core of the business today and the front door to everything we build next. You'll do the strategic product work on them yourself: deciding what needs to get built next, how the workspace and its AI evolve together, and where investment in craft pays off. As the group grows, you'll hire and manage a team of PMs.

Note: This role is open to US-based applicants only.

What you'll do- Set the vision and strategy for the Conversations group, and decide how Inbox and Copilot evolve together as one experience where AI makes every support pro faster without breaking their flow.

• Drive the Inbox roadmap hands-on: the workspace where every channel comes together and where our users spend their time in the product. This surface is held to a bar where speed, reliability, and polish are a differentiator.

• Drive the Copilot roadmap hands-on: integrations, contextual summaries, suggestions, and in-the-moment assistance that make each person on a support team meaningfully better at their job.

• Own how your products are monetized. Conversations spans seats and AI usage, and you'll design the packaging that makes each seat more valuable as Copilot does more. You'll collab...