Head of Product, Growth + Monetization - Help Scout

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.

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: Partner with Design and Engineering, but own the vision, roadmap, and execution for the Growth team. Start with sharpening the core funnel: signup, onboarding, trial-to-paid conversion, and activation moments.
• Run growth experimentation across the org: Build and run an experimentation practice spanning new business and expansion (getting existing customers to experience and purchase Agent, Copilot, and Signal products).
• Evolve Help Scout's monetization strategy: Own the overarching pricing and packaging framework across the portfolio, ensuring a cross-product throughline.
• Build growth infrastructure: Create the growth model, experiment standards, and playbooks that let teams across the company ship growth work with confidence.
• Lead as a player/coach: Drive strategy hands-on today, and hire and manage a team of PMs as the group grows.
• Partner across the customer lifecycle: Work closely with go-to-market, sales, customer success, and peer product leaders to keep the growth motion coherent.

About you

• 5+ years leading growth in B2B SaaS with a free-trial or freemium motion.
• Hands-on experience with experimentation, defining your own metrics, and designing tests.
• Think in outcomes, not features, building systems and playbooks that elevate the team.
• Ability to design an outcome-based pricing framework and explain its tradeoffs.
• Technically fluent enough to hold an architecture conversation and push back on engineering estimates.
• Exceptional leadership through influence, getting peer product teams to collaborate.
• Direct people management experience with a track record of hiring and coaching PMs.
• Excellent writer who makes thinking visible in one-pagers and briefs; fluent with AI tools for research synthesis and rapid prototyping.

Note: This role is open to US-based applicants only.