Head of HR

About Willow

Willow is a telehealth company focused on personalized, responsible cosmetic weight loss care. We combine medical expertise with a supportive, patient-centered approach to help people feel more confident and comfortable in their bodies. Our goal is to make high-quality care accessible, thoughtful, and designed to fit real lives.

HR operations and systems: Own the HR stack and employee lifecycle from offer acceptance through offboarding. Keep employee records, contracts, and documentation clean and audit-ready across the mix of employment types and geographies we operate in.

Employee relations: Be the senior, trusted operator for sensitive situations: investigations, disputes, accommodations, terminations. Handle them with discretion, fairness, and proper documentation. Coach managers so fewer situations escalate in the first place.

Compensation and benefits: Own comp philosophy, banding, and benchmarking, plus the benefits program. Make comp decisions consistent, explainable, and defensible, and run them in lockstep with finance: payroll, headcount planning, and comp changes should move through one tightly synced process between the two functions.

Performance management: Design and run a lightweight performance system: goals, feedback cadence, reviews, and calibration. Make it something managers actually use rather than an annual chore, and tie it into the company's existing management cadences rather than building a parallel system.

Employment compliance: Own employment law compliance across the states and countries where we have workers, including worker classification, payroll and benefits compliance, required policies, leave administration, and workplace requirements. Willow operates in a regulated healthcare space, and the HR function needs to hold the same standard on the employment side.

Recruitment collaboration: Partner with the recruiting function on offer strategy, hiring compliance, interview practices, new hire onboarding, and hiring manager coaching. Bring HR expertise and perspective to our recruitment processes.

Employee engagement and culture: Design and lead engagement initiatives and programs that keep the company connected as we scale. Advise on retention strategy and contribute to building a strong employee experience.

Team leadership: Manage and develop the People team, with clear ownership and priorities across the function.

Partner to leadership: Advise the COO and founders on org design, sensitive personnel matters, and people risk. Bring an independent, direct point of view.

• 8+ years in HR with at least 3 leading an HR function or major pillar at a company of comparable scale (roughly 150 to 500 people), ideally through a phase of rapid growth.

• Demonstrated experience building and scaling HR operations for both US-based employees and global workforce

• Deep employee relations experience. Has personally handled investigations, terminations, and leadership-level personnel matters, and can point to doing them well.

• Strong on employment compliance, ideally with multi-state experience; healthcare, telehealth, or another regulated industry is a real plus.

• Hands-on with comp: banding, benchmarking, and offer design, not just administering a system someone else built. Comfortable working hand in glove with finance.

• A builder's temperament. Comfortable being the most senior HR person in the company, making judgment calls without a big function around them.

• High discretion. This person will sit close to confidential matters from day one and needs to be someone founders and employees both trust.

• Direct, clear communicator who documents decisions and gives leadership honest, independent counsel.

• As full-time member of our team, you’ll enjoy:

• Flexible hours

• Work wherever you choose

• Fun and casual work environment

• Employee engagement activities and virtual gatherings

• We are a diverse, global team! 🌍