[Hiring] VP of People @Help Scout

Role Description

Help Scout is at a pivotal moment. We've laid the foundation of a strong, customer-loved product with a distinct brand and a mission-driven team. Now we're becoming an AI-driven organization with a new strategic narrative, a redefined ICP, and a go-to-market motion built to match. Our 2026 strategy is focused, ambitious, and rooted in clear outcomes, from pipeline and trials to customer expansion.

As VP of People, you'll step into a company with a strong remote-first culture ready to scale its reach and influence. You'll shape how we grow and differentiate ourselves as an employer of choice and bring our values to life at every stage of the team member journey.

This is a great opportunity to lead the people function at a company that believes in craft, autonomy, and building things that matter. You will help determine which of our People practices are scalable as they exist, and which need to change in order to scale effectively.

This is a hands-on leadership role in a remote-first company. You should expect high accountability, meaningful autonomy, and the opportunity to build, test, and refine how people drive growth at Help Scout.

About the role

• Lead a team that owns all aspects of the employee lifecycle, from recruiting and onboarding to people and organizational development.
• Oversee all programs including global compensation, organizational design, performance management, and employee retention and engagement.
• Ensure a robust and scalable culture, maintaining a strong values-driven and accountable culture.
• Own the systems that support remote work and collaboration.
• Define how to measure the health of our people and our People programs, maintaining that health and sharing progress regularly.
• Use data to guide decisions, challenge assumptions, and adjust strategy when necessary.
• Build and execute our talent strategy to ensure alignment and effectiveness of all people programs and practices.
• Bring an AI lens to everything, including how the People team uses AI to enhance efficiency.
• Drive Help Scout's new strategic narrative forward through our people.
• Establish clear planning, prioritization, and execution rhythms for your teams.

About You

• Served as a people leader at a scaling B2B SaaS company in the $30M–$150M ARR range.
• Led organizations through a growth stage with a focus on innovative work processes.
• Hands-on experience as an HRBP, understanding the partnership with the business.
• Genuine point of view on how AI can advance people practices.
• Creative in thinking about people strategies and innovative leadership approaches.
• Hold a high bar, elevate those around you, and communicate clearly and empathetically in a remote setting.
• Comfortable with shipping, measuring, and adjusting strategies.

Who you’ll work with

• Shawna Fisher – you’ll report to Shawna, our COO
• Toby Gabriner – our CEO
• Great people team members like Heidi, Julie, and Alison

Company values

• Happy to Help: We show up for each other, invested in the team’s collective success.
• Craft over Convention: Our success relies on the quality and craft of our work.
• Progress not Perfection: We create a culture of curiosity and openness for constant improvement.
• Own the Outcome: Taking full responsibility for the results of your work and decisions.

Benefits

• 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.
• Top tier health insurance for you and your dependents if you’re in the U.S. or Canada.