Head of People

Freshpaint is a remote U.S.-based startup that provides HIPAA-compliant data governance so healthcare organizations can use modern analytics and advertising tools while safeguarding patient privacy. The Head of People will be the first full-time people leader, responsible for building the people strategy and core HR functions to support scalable growth and a high-performing culture.

• Align people initiatives with business objectives to enable growth, operational efficiency, and cultural alignment.

• Own, build, and scale core people functions including People Ops, Recruiting, and Compliance.

• Partner with Finance and Operations on headcount planning, compensation strategy, and workforce forecasting.

• Develop and implement scalable frameworks for hiring rigor, performance standards, leveling, and compensation.

• Drive reduction in attrition and improve performance density through better hiring, onboarding, and manager enablement.

• Coach and develop leaders to strengthen managerial capability, accountability, and high performance.

• Lead organizational change efforts with clear communication and sustained employee engagement.

• Champion and evolve company values and culture, ensuring an inclusive and mission-aligned environment.

• Serve as a trusted advisor/mediator to promote transparency, trust, and collaboration across the organization.

• Oversee consistent and compliant employee lifecycle processes (onboarding, offboarding, and beyond).

• Advise leadership on organizational design, talent strategy, and workforce planning connected to revenue targets and product strategy.

• 5+ years of progressive HR/People leadership experience.

• At least 2+ years in a strategic HRBP or people strategy role, ideally in Series A/B or fast-growth organizations.

• Proven ability to build people functions from 0 to 1 with a mindset for scale.

• Hands-on leadership style with ability to flex between strategic and tactical execution.

• Understanding of systems theory and ability to translate business goals into effective people strategies.

• Strong employee-centric approach to development, inclusion, and workplace experience.

• Exceptional interpersonal and communication skills; ability to navigate complex situations and maintain transparency.

• Company-first mindset and comfort making hard decisions amid ambiguity.

• Nice to have: strengths in org design, performance management, talent development, and compensation strategy.

• Fully remote role; U.S. only hiring.

• Team offsites twice per year.

• $150/month coworking stipend.

• Half-day Fridays every Friday.

• Unlimited PTO with a required 2-week minimum.

• Health, dental, and vision insurance: 100% covered for employee, 80% for dependents.

• 2 “Treat Yourself” days per year ($100 plus a day off).

• Generous parental leave.

• Competitive pay plus generous equity (10-year exercise window).