Head of Product, Conversations - Help Scout

Who we are

Help Scout is a fully remote company building support software that treats customers like people. With over 10,000 customers globally, we are currently reimagining our platform for an AI-native world, focusing on shipping fast without compromising on craft.

Your impact

As the Head of Product for Conversations, you will own the vision, roadmap, and monetization for our core product lines: Inbox and Copilot. You will lead the surface where our users spend their entire day, ensuring that AI-driven assistance and human-centric support work in perfect harmony.

What you'll do

• Strategy & Vision: Define the evolution of Inbox and Copilot as a unified, AI-enhanced experience.
• Hands-on Execution: Drive roadmaps for both product lines, focusing on speed, reliability, and polish.
• Monetization: Design packaging strategies that scale with seat and AI usage.
• Cross-functional Leadership: Partner with the Autonomy group to ensure seamless integration between agent platforms and user workspaces.
• Team Building: Hire and mentor a team of Product Managers, coaching for high-level product judgment.
• Customer Focus: Maintain deep proximity to customer needs to inform product direction.

What we're looking for

• Proven experience owning core products at scale in a B2B SaaS environment.
• Demonstrated success shipping AI-powered products.
• Strong commercial instincts with experience in monetization and packaging.
• Ability to manage and coach PMs while remaining hands-on with strategy.
• Excellent written communication skills; you make your thinking visible through clear, concise documentation.
• Technical fluency to collaborate effectively with engineering teams on architecture and system design.
• Data-driven mindset; you are self-sufficient in pulling and analyzing data to pressure-test decisions.

Benefits

• Competitive salary with a transparent formula.
• Flexible time off and 12 weeks of fully paid parental leave.
• Home office and co-working stipends.
• $1,800 annual professional development stipend.
• Top-tier health insurance for U.S. employees and dependents.

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