Director of Retail Development

Proper Cloth

3d•$165,000 - $185,000•Hybrid

About The Position

We are seeking a Director of Retail Development to manage the end-to-end process of showroom expansion. This includes building relationships with developers and brokers, understanding market dynamics and spaces, managing the lease process, directing architects and contractors, and ensuring projects are completed within budget. The role involves building a pipeline of new locations to accelerate growth over time and refining a repeatable playbook for faster and more efficient openings. This position reports directly to the CEO. Proper Cloth is the world's largest men's custom shirtmaker, with a growing presence in custom suiting and broader premium menswear. Founded in 2008, the company has achieved over $65M in annual revenue without external funding. Headquartered in Soho, New York, Proper Cloth has four showrooms in New York (Fifth Avenue and Soho), Chicago, and Washington, D.C., and a team of over 100 employees. Our vision is to become America's most loved menswear brand, a modern luxury brand characterized by exceptional quality, personalized fit, and concierge-level service. We believe in beautifully designed, well-made, custom-fit clothing paired with exceptional service. Showrooms are the optimal format for delivering this luxury customer experience, and expanding our showroom network across major US cities is crucial for achieving this goal. We are evaluating a dozen potential markets for expansion, including San Francisco, Los Angeles, Seattle, Denver, Austin, Dallas, Houston, Atlanta, Miami, Palm Beach, Philadelphia, and Boston. Our showrooms are a unique retail concept, operating on an appointment-based model with less reliance on street visibility or walk-in traffic. They feature product displays for viewing, touching, and trying on, but do not stock inventory for direct purchase. The spaces are designed to be calm and quiet, resembling a private tailor atelier rather than a traditional clothing store. Customers work with sales associates for measurements, fitting garment try-ons, size creation, and garment customization. This model presents distinct real-estate requirements, challenges, and advantages.

Requirements

Six or more years in retail store development, retail construction project management, or owner's representation
Direct hands-on involvement in at least three store openings
Experience running multiple concurrent build-outs in different cities
Ability to select and direct outside teams: architects, GCs, expediters, vendors
Ability to read a bid and identify discrepancies in scope and cost
Fluency in lease business terms (effective vs. asking rent, TI allowance, free rent, escalations, NNN caps, loss factor, exclusivity, co-tenancy, assignment and sublease rights)
Excellent taste and an eye for premium design
Excellent written and verbal communication skills
Resourceful and well-networked, or able to build a network quickly
Willingness to travel meaningfully (15–40%)

Nice To Haves

Premium or luxury retail experience
Experience with appointment-based, clienteling, or by-referral formats
Landlord- or developer-side leasing experience
Experience opening in two or more of our target markets
Architectural experience with the ability to update CAD files or do test layouts