Head of Product, Growth + Monetization

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. More than 10,000 businesses use us, and a remarkable share of them arrived because someone they respect recommended us. That trust is also why customers stay and grow with us once they’re in the door. Growth is how more of the people who show up turn into teams who can’t imagine working without Help Scout — and how customers who already love one part of the product find their way into what’s next. As Head of Product, Growth & Monetization, you’ll be directly accountable for both sides of that story: the core funnel that turns a signup into a paying customer, and the in-app motion that turns a paying customer into an expanding one. About the role • Own the growth roadmap. You’ll partner with Design and Engineering, but you’ll own the vision, roadmap, and execution for the Growth team. That starts with sharpening the core funnel: signup, onboarding, trial-to-paid conversion, and the activation moments that turn a trial into a team that can’t imagine working without Help Scout. • Run growth experimentation across the org. Build and run an experimentation practice spanning two swim lanes: new business (signup through trial-to-paid) and expansion (getting existing customers to experience and purchase Agent, Copilot, and Signal products). The expansion lane means designing and running experiments inside product lines you don’t own, in partnership with the other product leaders who do. • Evolve Help Scout’s monetization strategy. Own the overarching pricing and packaging framework across the portfolio. Each Head of Product still owns pricing and packaging execution for their own line — your job is the cross-product throughline and the judgment to know when to weigh in. • Build growth infrastructure other teams can use. Create the growth model, experiment standards, and playbooks that let teams across the company ship growth work with confidence, without routing every decision through you. • Lead as a player/coach. Do the strategic work yourself today, and hire and manage a team of PMs as the group grows. You’re accountable for the group’s revenue results, not just its roadmap execution. • Partner across the customer lifecycle. Work with go-to-market so the growth motion is coherent from first touch through expansion, and spend real time with customers and in the data to keep that motion grounded in what’s actually true. About you • You’ve spent 5+ years leading growth in B2B SaaS with a free-trial or freemium motion, and you have a concrete story of moving a product line’s revenue or adoption. • You’re hands-on with experimentation. You define your own metrics, design your own tests, and you’re honest about when a result is signal versus noise. • You think in outcomes, not features, and you build systems and playbooks that make everyone around you faster, not just wins that end with you. • You can design an outcome-based pricing framework and explain its tradeoffs, and you understand the difference between owning strategy and owning someone else’s execution. • You’re technically fluent enough to hold an architecture conversation and push back credibly on an engineering estimate, and you understand how AI and agentic product features actually fail, not just how they work when they work. • You lead through influence as much as authority. Your impact here comes from getting peer product teams to want to run your experiments with you. • You’ve directly managed people before. You’ll hire and coach a team of PMs as this group grows. • You’re an excellent writer who makes your thinking visible in one-pagers and briefs that move decisions forward, and you’re genuinely fluent with AI tools for research synthesis, strategy testing, and rapid prototyping. Who you’ll work with • Chief Product Officer. You report to the CPO and partner closely with them on strategy and monetization. • Head of Product, Conversations. You partner on expansion experiments and the monetization framework for Inbox and Copilot. • Head of Product, Intelligence. You partner on expansion experiments and the monetization framework for Agent and Signal. • Marketing leadership. You align the growth motion with campaigns, messaging, and pricing/packaging changes. • Sales & Customer Success leadership. You keep the growth motion coherent across the full customer lifecycle, from trial through expansion and renewal. • Growth PMs. As the group grows, a small team of PMs may report to you. Note: This role is open to US-based applicants only. 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.