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Help Scout is a customer support software company founded in 2011 that has processed 3+ billion conversations for 10,000+ companies. The company is undergoing a strategic transformation to become AI-native while maintaining its commitment to craft and customer-centric values. With 120+ fully remote team members globally, Help Scout is scaling its go-to-market motion and redefining its market positioning.
As VP of People, you will lead the entire people function during a pivotal growth phase. You'll report directly to the COO (Shawna Fisher) and work closely with the CEO and existing people team members. This is a hands-on leadership role with high accountability and meaningful autonomy.
Key responsibilities include:
- Leading a team that owns the complete employee lifecycle: recruiting, onboarding, organizational development, compensation, performance management, retention, and engagement
- Building and maintaining a scalable, values-driven remote-first culture with robust systems for collaboration and accountability
- Defining metrics to measure people and program health, using data to guide decisions and adjust strategy
- Developing and executing a comprehensive talent strategy aligned with business needs, including recruiting strategy and hiring manager support
- Bringing an AI lens to people operations—both how the people team uses AI internally and how to help all team members leverage AI more effectively
- Aligning people programs with Help Scout's new strategic narrative and business outcomes
- Establishing clear planning, prioritization, and execution rhythms for team clarity and performance
Help Scout's culture emphasizes four core values: Happy to Help (generosity and empathy), Craft Over Convention (quality and attention to detail), Progress Not Perfection (curiosity and learning), and Own the Outcome (accountability and proactivity).
Benefits include competitive salary with transparent market-based formula, flexible time off, 12 weeks fully paid parental leave, home office stipend, co-working stipend up to $300/month, $1,800 annual professional development stipend, and top-tier health insurance for US/Canada-based employees.
REQUIREMENTS:
- Experience as a people leader at a scaling B2B SaaS company in the $30M–$150M ARR range
- Track record leading organizations through growth stages and driving organizational change
- Hands-on HRBP experience with deep understanding of business partnership
- Genuine perspective on how AI can advance people practices—not just as tools but as a shift in how individuals and teams operate
- Creative approach to people strategy and innovative leadership thinking
- High standards, ability to elevate others, clear and empathetic communication in remote settings
- Comfort with shipping, measuring, and adjusting; ability to balance performance goals with long-term vision
