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Help Scout is a customer support platform used by 10,000+ companies to manage customer relationships. Founded in 2011, the company has processed 3+ billion conversations and operates as a fully remote team of 120+ people globally.
As Head of Product, Growth & Monetization, you will own the complete growth and monetization strategy for Help Scout's product portfolio. Your responsibilities include:
**Core Responsibilities:**
- Own the growth roadmap and vision, partnering with Design and Engineering to execute. Focus on the core funnel: signup, onboarding, trial-to-paid conversion, and activation moments that turn trials into committed teams.
- Build and run an experimentation practice across two swim lanes: new business (signup through trial-to-paid) and expansion (getting existing customers to adopt Agent, Copilot, and Signal products). This includes designing experiments inside product lines you don't directly own, in partnership with other product leaders.
- Evolve Help Scout's monetization strategy by owning the overarching pricing and packaging framework across the portfolio. Provide cross-product guidance while allowing individual product heads to execute within their lines.
- Create growth infrastructure (growth models, experiment standards, playbooks) that enable teams across the company to ship growth work independently.
- Lead as a player-coach: do strategic work yourself today while hiring and managing a team of PMs as the group grows. You are accountable for the group's revenue results.
- Partner across the customer lifecycle with go-to-market, sales, and customer success teams to ensure coherent growth motion from first touch through expansion. Stay grounded in customer insights and data.
**Reporting and Collaboration:**
You report to the Chief Product Officer and partner closely with Heads of Product for Conversations and Intelligence, marketing leadership, and sales/customer success leadership.
**Requirements:**
- 5+ years leading growth in B2B SaaS with a free-trial or freemium motion, with a concrete track record of moving a product line's revenue or adoption.
- Hands-on with experimentation: you define metrics, design tests, and distinguish signal from noise.
- Outcome-focused mindset with ability to build systems and playbooks that make teams faster.
- Can design outcome-based pricing frameworks and explain tradeoffs; understands the difference between owning strategy versus owning someone else's execution.
- Technical fluency sufficient to hold architecture conversations, push back credibly on engineering estimates, and understand how AI and agentic features actually fail in practice.
- Lead through influence and peer relationships; ability to get product teams to want to run experiments with you.
- Direct people management experience; will hire and coach a team of PMs.
- Excellent writer who creates clear one-pagers and briefs that move decisions forward.
- Fluent with AI tools for research synthesis, strategy testing, and rapid prototyping.
