VP of People at Help Scout

Help Scout is seeking a VP of People to lead its remote-first team of 120+ employees globally. This is a hands-on leadership role focused on shaping the company’s people strategy, culture, and growth as Help Scout transitions into an AI-driven organization.

Your Impact

Help Scout is at a pivotal moment, redefining its strategic narrative, customer focus, and go-to-market approach. As VP of People, you will:

• Lead all aspects of the employee lifecycle, including recruiting, onboarding, organizational development, compensation, performance management, and retention.
• Ensure a scalable, values-driven culture in a remote-first environment, addressing unique challenges and opportunities.
• Define and maintain metrics for people health and program effectiveness, using data to guide decisions and refine strategy.
• Build and execute a talent strategy aligned with business growth, including a robust recruiting framework and AI-driven people practices.
• Integrate AI into people operations, leveraging it to enhance efficiency, collaboration, and decision-making across the team.
• Align people programs with Help Scout’s 2026 strategy, ensuring seamless integration with business goals.
• Establish clear planning, prioritization, and execution rhythms to optimize team performance.

About You

Ideal candidates have:

• 5+ years of experience as a people leader in a scaling B2B SaaS company ($30M–$150M ARR).
• Proven ability to lead organizations through growth stages and adapt to evolving work environments.
• Hands-on HRBP experience, with a deep understanding of business partnership and people strategy.
• A strong point of view on AI’s role in advancing people practices, not just as tools but as a cultural shift.
• Creative, innovative approaches to leadership and people development, ensuring high performance and engagement.
• High accountability, autonomy, and the ability to balance short-term goals with long-term vision.
• Experience leading in a remote setting, with strong communication and empathy skills.

Who You’ll Work With

You’ll report to Shawna Fisher (COO) and collaborate closely with Toby Gabriner (CEO), as well as the existing People team (e.g., Heidi, Julie, Allison).

Company Values

• Happy to Help: Generosity, knowledge-sharing, and empathy in teamwork.
• Craft over Convention: Narrow focus, detail-oriented work, and relentless pursuit of excellence.
• Progress not Perfection: Embracing mistakes as learning opportunities.
• Own the Outcome: Accountability, proactivity, and problem-solving mindset.

Benefits and Perks

• Competitive salary with transparent market-based compensation.
• Flexible time off and 12 weeks of paid parental leave.
• Home office and co-working stipends ($300/month).
• $1,800 annual professional development stipend.
• Top-tier health insurance (U.S./Canada).