Note: The job is a remote job and is open to candidates in USA. Help Scout is a fully remote customer support software company focused on helping teams grow relationships with customers. As Head of Product, Growth & Monetization, you will own the growth roadmap, experimentation practice, and cross-product monetization strategy to improve signup-to-paid conversion and customer expansion.

Responsibilities

• 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

Skills

• • 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

Benefits

• Fully remote
• 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.

Company Overview