Director of People

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.

About the Role

We're hiring a Director of People to lead our People department and personally run its HR operations. This is a hands-on leadership role: you'll own the technical side of HR yourself (compensation, employee relations, compliance, people systems) while leading a department that also includes our Culture & Development function and its head. You'll report to the COO and act as a trusted advisor to leadership across the company.

Responsibilities

• HR operations and systems. Own our HR stack and the employee lifecycle from offer acceptance through offboarding, keeping documentation clean and compliant across a mix of employment types in multiple countries.

• Employee relations. Act as the company's lead on sensitive matters: investigations, grievances, accommodations, and separations. Handle them with care and airtight documentation, and coach managers so that fewer issues escalate in the first place.

• Compensation and benefits. Own our compensation framework: pay bands, market benchmarking, and our benefits programs. Keep decisions consistent and defensible, and work closely with finance on payroll, workforce planning, and the pay change process.

• Performance management. Run lightweight performance mechanics (goals, feedback cycles, reviews, calibration) that plug into how our leaders already work rather than adding process for its own sake.

• Employment compliance. Own compliance across every jurisdiction we employ in: worker classification, payroll and benefits rules, required documentation, leave, and workplace standards, all within a regulated healthcare context.

• Recruiting partnership. Partner with recruiting on offer frameworks, compliant hiring practices, interview process, onboarding handoffs, and developing our leaders as hiring managers.

• Department leadership. Lead the People department as a whole. Our Culture & Development function, which owns onboarding, training, culture programs, and engagement, reports to you through its head; your job is to align the two sides of the department, develop its leaders, and be accountable for the department's goals.

• Partner to leadership. Advise the leadership team on org design, sensitive people matters, and people risk, with an independent, candid point of view.

Requirements

• 8+ years in HR, including 3+ years leading an HR function or a major part of one at a company of 150 to 500 people, ideally through a period of growth.

• A track record of building and scaling HR infrastructure for both domestic and international teams.

• Deep hands-on employee relations experience: you have personally run investigations, terminations, and senior-level personnel situations.

• Strong multi-state employment compliance knowledge; experience in a regulated industry (healthcare, telehealth) preferred.

• Real compensation skills (pay architecture, benchmarking, offer construction), not just systems administration, and the ability to partner with finance.

• Experience managing senior HR or People professionals well; you lead an established function's owner as a coach and advocate, and you stay hands-on yourself rather than delegating the technical work.

• An owner's mentality: comfortable as the senior HR voice in the company, exercising independent judgment.

• Impeccable discretion: trusted by leadership and employees alike, a clear communicator who documents reasoning and gives unbiased guidance.

What’s in it for you?

• 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! 🌍