[Hiring] Head of HR @Willow Health

Role Description

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.

Responsibilities

• 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.

Qualifications

• 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.

Benefits

• Flexible hours
• Work wherever you choose
• Fun and casual work environment
• Employee engagement activities and virtual gatherings
• We are a diverse, global team! 🌍