VP of People - 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.

This role is 100% remote and open to US-based candidates at this time.

Your Impact

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 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, global compensation, organizational design, performance management, and employee retention and engagement.
• Ensure a robust and scalable culture by maintaining a strong values-driven and accountable environment, and owning the systems that support remote work and collaboration.
• Define how we measure the health of our people and People programs, regularly sharing progress at the leadership level and using data to guide decisions.
• Build and execute a talent strategy to ensure all people programs and practices are aligned and effective.
• Bring an AI lens to everything, including how the People team uses AI to move faster and how all team members better leverage AI to work effectively.
• Drive Help Scout's new strategic narrative forward through our people, aligning programs to business needs seamlessly.
• Establish clear planning, prioritization, and execution rhythms that provide clarity to 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 and know what it takes to get people thinking differently about getting work done in a changing environment.
• Hands-on experience as an HRBP with a deep understanding of what it means to be a partner to the business.
• Genuine point of view on how AI can advance organizations’ people practices.
• Creative in thinking about people and people strategies, leveraging innovative leadership approaches.
• Hold a high bar, elevate those around you, and communicate clearly and empathetically in a remote setting.
• Like to ship, measure, and adjust without being afraid of the tension between performance goals and long-term vision.

Benefits and Perks

• Competitive salary and an internal, transparent salary formula based on market data
• Flexible time off
• 12 weeks of fully paid parental leave for all new parents, including adoption and foster care
• A home office stipend
• A co-working stipend up to $300 a month
• A yearly professional development stipend of $1,800
• Top tier health insurance for you and your dependents (U.S. and Canada)