VP of People

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.

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.

About You

• You've served as a people leader at a scaling B2B SaaS company in the $30M–$150M ARR range.

• You've led organizations through a growth stage and you know what it takes to get people thinking differently about how to get work done in a changing environment.

• You've had hands-on experience as an HRBP in your career. You deeply understand what it means to be a partner to the business.

• You have a genuine point of view on how AI can advance organizations’ people practices – not just as a set of tools, but as a shift in how individuals and teams operate. You're excited to put that into practice.

• You are creative in thinking about people and people strategies. You leveraging innovative approaches in leadership to ensure people can perform at their best and have a great experience.

• You hold a high bar, elevate those around you, and communicate clearly and empathetically in a remote setting.

• You like to ship, measure, adjust. You aren't afraid of the tension between performance goals and long-term vision.

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 Allison

Company values

Happy to Help

Help is in our first name! We show up for each other — not out of obligation, but because we’re invested in the team’s collective success. We share knowledge freely, lead with generosity, and practice empathy with our teammates, customers, and community.

Craft over Convention

Our success relies on the quality and craft of the work we put into the world. The status quo simply won’t work. So we insist on narrow focus, sweating every detail, and relentless pursuit of customer delight.

Progress not Perfection

Achieving our true potential — collectively and individually — requires constant progress and forward momentum. By creating a culture of curiosity and openness, we aim to create a safe space for mistakes, the ability to identify them quickly, and use them to get better.

Own the Outcome

Own the outcome means taking full responsibility for the results of your work, decisions, and contributions. It reflects a mindset of accountability, proactiveness, and follow-through. If you “own the outcome,” you don’t just complete tasks, you ensure your work leads to meaningful results, and take initiative to solve problems rather than passing them along.

Read more about how we define, share, and live these values here.

Benefits And Perks

• 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

• If you’re in the U.S. or Canada, we offer top tier health insurance for you and your dependents.

Hiring Guidelines:

All roles at Help Scout are fully remote. Some positions have specific location requirements. For roles outside the U.S. and Canada, we work with teammates as independent contractors under country-specific agreements.

We do not sponsor visas. Teammates must already be authorized to work from their home country.

We are an equal opportunity employer and are committed to building a company that embraces and celebrates diversity and inclusion. We do not discriminate on the basis of race, religion, color, national origin, gender, gender identity or expression, sexual orientation, age, marital status, veteran status, or disability status. We have read the studies and understand that diverse teams build better products, bring more perspective to the table, contribute to a company’s financial success, and help foster a more inclusive environment for all employees, but the bottom line is that it's the right thing to do.

To provide you with the best experience, we can support you with accommodations or adjustments at any stage of the recruitment process. Simply inform our recruitment team during your conversation with them.

A note on the use of AI in our interview process

While we understand that AI is an important tool in a modern skillset, we ask that you do not utilize AI assistants live on our interviews. Of course, use any tools you need to prepare! But we'd like for you to have a real human-to-human conversation with our team.

On our end, we utilize a platform called Brighthire as a notetaker and review tool to ensure a fair and transparent hiring process.

Beware of scammers! All legitimate communication from Help Scout regarding your application will come directly from an @helpscout.com email address and through our applicant tracking system, Ashby. We will never ask for personal financial information or conduct interviews outside of these official channels.