Director of People & Operations

Watson Style Group is a luxury personal styling firm serving private clients across the country — a small team, a high-touch service, and a business growing fast on the strength of long-term client relationships. We've built our own technology platform and we run lean: every person here owns their function fully. We have studios in New York and Chicago.

The Role

The Director of People & Operations reports to the Managing Partner and owns the human and operational machinery of the company end-to-end — running it autonomously.

We are explicitly not hiring a coordinator who needs direction. We're hiring the person who takes this entire function off the leadership team's plate.

What You'll Own

• Hiring, onboarding, and performance reviews for a growing styling team — sourcing through closing
• Benefits, our PEO relationship, payroll compliance, and the day-to-day HR machine
• Culture, coaching, and retention — keeping exceptional people growing here
• Our outside-counsel relationship: employment agreements, client agreements, terms
• Vendor relationships and procurement — shipping, tailoring, and logistics partners
• Administration of our brand and retail partner agreements — contracts, commission tracking, and collections (commercial negotiation stays with leadership)
• Client and partner events in New York, from vendor contracting to flawless on-site execution
• A small shared-services team (logistics and administration)

What You Won't Own

Company strategy, revenue and commercial deal-making, and styling craft live elsewhere — by design. Clear lanes are a feature of how we work. You make the team thrive; you'll always know exactly where your authority begins and ends.

Who You Are

• 5–8+ years in people and/or operations, including 2–3 years as the most senior (or only) people/ops person at a company under 100 people
• You've personally run a PEO or payroll, a benefits renewal, and multi-state employment compliance — not overseen someone doing it
• You've worked directly with employment counsel on offers and agreements
• You've negotiated real vendor contracts and produced real events
• High emotional intelligence and absolute discretion — you're the person trusted alone in the room with the sensitive thing
• Based in New York or Chicago — we have studios in both. You'll travel regularly between the two and be on-site for all New York events and vendor partners; a background in luxury, hospitality, or high-end client services is strongly preferred

Compensation

Discretion guaranteed. We will not contact your current employer at any stage of the process. Conversations are held in confidence until you choose otherwise.

Watson Style Group is an equal opportunity employer. We are committed to building a team that reflects the diversity of the clients we serve. All qualified applicants will receive consideration without regard to any protected characteristic under applicable law.