Head of Product, Conversations

Who we are

Help 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 impact

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 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 role

You'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.

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 collaborate with partners across Help Scout to model the impact of the products you ship.
• Partner deeply with the Autonomy group. Significant parts of Copilot run on the agent platform, and likewise, Agent hands conversations to humans in your workspace. The seams between the two groups are owned jointly, and making them invisible to customers is part of the job.
• Spend real time with customers, understanding how support pros and their leaders actually work, where AI helps, and where it gets in the way.
• Partner with GTM and CS so the Conversations story is clear, the adoption motion is tight, and customer feedback loops back into the roadmap.
• Build and manage the Conversations PM team as it grows, coaching for judgment and raising the bar for product craft across the group.

What we're looking for

• You've owned a core product at scale, the kind people spend their whole workday in, and you're as fluent in the commercial side of product as you are in features and user experience.
• You've shipped AI-powered products and you understand how they succeed and fail.
• You collaborate well across ownership lines and know how to co-own a product surface with a peer while keeping the seams invisible to customers.
• You think in outcomes, including time to resolution, drafts accepted, and team efficiency.
• You care about craft and hold a roadmap accountable to speed, calm, and reliability.
• You have strong monetization instincts and can package a product line that spans seats and outcomes.
• You've managed product managers before and still love doing the work yourself.
• You're data self-sufficient and use numbers to pressure-test direction.
• You're technically fluent enough to build genuine trust with engineers and discuss system architecture meaningfully.
• You're fluent with AI tools for research synthesis, strategy testing, rapid prototyping, and customer signal analysis.
• You understand that when execution is cheap, judgment is the bottleneck.
• You're an excellent writer who makes thinking visible in one-pagers, briefs, and narratives.
• You've worked in B2B SaaS and understand the difference between building for support teams and end consumers.

Company values

Happy to Help

Help is in our first name! We show up for each other, share knowledge freely, lead with generosity, and practice empathy with our teammates, customers, and community.

Craft over Convention

Our success relies on the quality and craft of the work we put into the world. We insist on narrow focus, sweating every detail, and relentless pursuit of customer delight.

Progress not Perfection

Achieving our true potential requires constant progress and forward momentum. We create a culture of curiosity and openness, identify mistakes quickly, and use them to get better.

Own the Outcome

Own the outcome means taking full responsibility for the results of your work, decisions, and contributions. It reflects accountability, proactiveness, and follow-through.

Benefits And Perks

• Competitive salary and an internal, transparent salary formula based on market data.
• Flexible time off.
• 12 weeks of fully paid parental leave for all new parents, including adoption and foster care.
• A home office stipend.
• A co-working stipend up to $300 a month.
• A yearly professional development stipend of $1,800.
• Top tier health insurance for employees and dependents in the U.S. or Canada.

Hiring Guidelines

All roles at Help Scout are fully remote. Some positions have specific location requirements. For roles outside the U.S. and Canada, Help Scout works with teammates as independent contractors under country-specific agreements.

Help Scout does not sponsor visas. Teammates must already be authorized to work from their home country.

Help Scout can provide accommodations or adjustments at any stage of the recruitment process.

A note on the use of AI in our interview process

Candidates are asked not to use AI assistants live during interviews, though they may use tools to prepare. Help Scout uses Brighthire as a notetaker and review tool to support a fair and transparent hiring process.

Candidates should beware of scammers. Legitimate communication from Help Scout regarding applications comes from an @helpscout.com email address and through Ashby. Help Scout will never ask for personal financial information or conduct interviews outside official channels.