VP of People at Helpscout

Source: Helpscout’s job board on Ashby, checked today.

Written by the listing’s owner or source, not by Openpath.

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 [website removed] 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. If that kind of challenge gives you energy, we’d love to meet you. 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 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 - You'll lead a team that owns all aspects of the employee lifecycle, from recruiting and onboarding to people and organizational development, as well as all programs including global compensation, organizational design, performance management, and employee retention and engagement. - You'll ensure we have a robust and scalable culture. Being a remote-first company comes with unique opportunities and challenges. You and your team lead the charge in maintaining a strong values-driven and accountable culture. You'll also own the systems that support remote work and collaboration. - You'll define how we measure the health of our people and our People programs, maintain that health, and regularly share progress at the leadership level and across the business. You'll use data to guide decisions, challenge assumptions, and adjust strategy when the signal changes. - You'll build our talent strategy and execute against it to ensure all our people programs and practices are aligned and effective, including a robust recruiting strategy and partnership to support hiring managers through the process. - You'll bring an AI lens to everything, including how the People team uses AI to move faster and sharpen how they work, and helping all team members better leverage AI to work more effectively. - You'll drive Help Scout's new strategic narrative forward through our people. Our business is nothing without our people. You’ll align our People programs to our business needs in a seamless and integrated way. - You'll establish clear planning, prioritization, and execution rhythms that provide clarity to your teams so they can operate at their best. …