Director of People

Department: Operations

Location: United States (Remote), Canada (Remote)

Employment Type: FullTime

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

Were hiring a Director of People to lead our People department and personally run its HR operations. This is a hands-on leadership role: youll 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. Youll 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 companys 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 departments 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 functions owner as a coach and advocate, and you stay hands-on yourself rather than delegating the technical work.

• An owners 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! 🌍