Head of Products - Remote

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. fully remote team

It’s a culture where you’ll be trusted to take ownership, stay curious, and raise the quality of work around you. 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. Now it's the foundation for something bigger.

Our path to $100M ARR runs through outcome-based products: resolutions handled, drafts sent, actions taken on behalf of a customer. 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. The trust ladder we're building — from assisted drafts to autonomous answers to agentic actions — is a product philosophy as much as a roadmap. 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.

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

You have shipped AI-powered products and understand how they fail — not just how they work when they work

Resolutions handled" and "drafts sent" are more interesting to you than "new settings page launched"

You can design a pricing surface that reflects real customer value and explain the tradeoffs when you can't

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. 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

Happy to Help

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

Our success relies on the quality and

So we insist on narrow focus, sweating every detail, and relentless pursuit of customer delight.

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

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

S. or Canada, we offer top tier health insurance for you and your dependents.

All roles at Help Scout are fully remote. 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. On our end, we utilize a platform called Brighthire as a notetaker and review tool to ensure a fair and transparent hiring process.

All legitimate communication from Help Scout regarding your application will come directly from an

@ 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.