Lead/Principal Product Manager, Agents

Who we are

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.

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, no matter who or what handles it, should feel like it came from someone who cares. That trust took a decade to build. Now it's the foundation for something bigger.

The support industry is changing shape. AI will handle more of what support teams used to do. Seat revenue will compress. That's not a threat to manage — it's the condition we're designing for. Our path to $100M ARR runs through outcome-based products: resolutions handled, drafts sent, actions taken on behalf of a customer. The Agent pillar is how we get there.

But here's what makes Help Scout's version different: our customers are compliance-driven, trust-cautious, and deeply invested in how their customers feel. They're not looking for AI that moves fast and breaks things. They need AI that earns its place — one step at a time, with evidence. The trust ladder we're building — from assisted drafts to autonomous answers to agentic actions — is a product philosophy as much as a roadmap. Your job is to make every rung feel inevitable.

About the Role

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.

This role is currently open to consideration at 2 levels. The compensation range reflects the range across both levels.

What You'll Do

• 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

What We're Looking For

• 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 synthesis, strategy testing, rapid prototyping, and customer signal analysis. You have a point of view on where these tools are heading and how they're changing the shape of PM work

• You understand that when execution is cheap, judgment is the bottleneck. Your highest-leverage hours are spent on strategy and prioritization — defining what's next and what's not — not on driving the build

• You're an excellent writer. Help Scout runs on writing, and you make your thinking visible in one-pagers, briefs, and narratives that move decisions forward

• You've worked in B2B SaaS and understand the difference between building for support teams vs. building for end consumers

Company values

Happy to Help

Help is in our first name! We show up for each other — not out of obligation, but because we’re invested in the team’s collective success. We 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. The status quo simply won’t work. So we insist on narrow focus, sweating every detail, and relentless pursuit of customer delight.

Progress not Perfection

Achieving our true potential — collectively and individually — requires constant progress and forward momentum. By creating a culture of curiosity and openness, we aim to create a safe space for mistakes, the ability to identify them 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 a mindset of accountability, proactiveness, and follow-through. If you “own the outcome,” you don’t just complete tasks, you ensure your work leads to meaningful results, and take initiative to solve problems rather than passing them along.

Read more about how we define, share, and live these values here.

Benefits And Perks

• 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

• If you’re in the U.S. or Canada, we offer top tier health insurance for you and your dependents.

Hiring Guidelines:

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

We do not sponsor visas. Teammates must already be authorized to work from their home country.

We are an equal opportunity employer and are committed to building a company that embraces and celebrates diversity and inclusion. We do not discriminate on the basis of race, religion, color, national origin, gender, gender identity or expression, sexual orientation, age, marital status, veteran status, or disability status. We have read the studies and understand that diverse teams build better products, bring more perspective to the table, contribute to a company’s financial success, and help foster a more inclusive environment for all employees, but the bottom line is that it's the right thing to do.

To provide you with the best experience, we can support you with accommodations or adjustments at any stage of the recruitment process. Simply inform our recruitment team during your conversation with them.

A note on the use of AI in our interview process

While we understand that AI is an important tool in a modern skillset, we ask that you do not utilize AI assistants live on our interviews. Of course, use any tools you need to prepare! But we'd like for you to have a real human-to-human conversation with our team.

On our end, we utilize a platform called Brighthire as a notetaker and review tool to ensure a fair and transparent hiring process.

Beware of scammers! All legitimate communication from Help Scout regarding your application will come directly from an @helpscout.com email address and through our applicant tracking system, Ashby. We will never ask for personal financial information or conduct interviews outside of these official channels.