Director of Retail Development

Director of Retail Development

Proper Cloth · United States (Remote) · Full-time · Posted 2026-08-10

Salary: USD 165,000–185,000

Workplace: remote

Department: Operations

Description

We're looking for someone to drive showroom expansion end to end: building relationships with developers and brokers, understanding the markets and the spaces, running the lease process, directing architects and contractors, and delivering finished showrooms on budget.

This is not a one-store-at-a-time job. Rather, we will be building a pipeline of new locations such that our pace accelerates over time — a few projects in motion now, more next year. Furthermore, we’ll be refining a repeatable playbook that makes each opening faster and better than the last.

This role will report directly to the CEO.

About Proper Cloth

Today

Today Proper Cloth is the largest men's custom shirtmaker in the world, a growing force in custom suiting, and an emerging contender in the broader luxury/premium menswear category. Established in 2008, we are a founder-led business that has grown profitably to over $65M in annual revenue without external capital or debt. Headquartered in Soho, New York, we have four showrooms: in New York (Fifth Avenue and Soho), Chicago, and Washington, D.C., and a dedicated team of over 100 employees.

Our Vision

Our vision is to build the most loved menswear brand in America — a modern luxury brand defined by exceptional quality, personalized fit, and concierge-level service. We believe true luxury is beautifully designed, exceptionally well-made clothing, custom-fit to the customer, paired with hands-on service that supports the customer every step of the way. We have found that our showrooms are the best format for us to deliver that luxury customer experience. Expanding and scaling our showroom network across all major US cities will be a key step in becoming a household luxury name.

Target Markets

Beyond our existing showrooms, we're evaluating a dozen potential markets for expansion: San Francisco, Los Angeles, Seattle, Denver, Austin, Dallas, Houston, Atlanta, Miami, Palm Beach, Philadelphia, and Boston.

A Unique Retail Concept

Our showrooms are different than traditional retail. They are appointment based and less dependant on street level visibility or walk-in traffic. We feature a wealth of product on display to view, touch, and try-on, but no inventory is stocked to be purchased directly. The spaces are calm and quiet - more akin to a private tailor atelier than to a traditional clothing store. Customers work directly with a sales associate, who helps measure them, try on fitting garments, create their custom size, shop the collection and customize their garments. As a result, we have different real-estate requirements, creating both challenges and advantages.

Requirements

• Six or more years in retail store development, retail construction project management, or owner's representation, with 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. You know how to read a bid and find where the scope and the money don't match.
• Fluency in lease business terms: effective versus asking rent, TI allowance, free rent, escalations, NNN caps, loss factor, exclusivity, co-tenancy, assignment and sublease rights.
• Excellent taste, and specifically an eye for premium design. You'll be selecting finishes, reviewing drawings with architects.
• Excellent written and verbal communication. You'll be pitching developers and presenting options to the CEO.
• Resourceful and well-networked, or able to build a network fast in cities where you don't have one.
• Willingness to travel meaningfully. Expect 15–40%, weighted toward periods of active pipeline development.

Strongly Preferred

• Premium or luxury retail experience, or 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.

Details

• Location: New York, based in our Soho office, or US based Remote (this is a travel-heavy role, not a work-from-home one. Expect to be on-site in target markets 15–40% of the time, more during active pipeline periods.)
• Reports to: CEO

To Apply

Send a résumé and a short note covering:

1. The store opening you're proudest of, and the one that went worst. What you'd do differently on the second one.
2. A retail or hospitality space you think is exceptionally well executed — a photo or a link, and two or three sentences on why. Any budget level, anywhere in the world.

We read all of these.

Benefits

• Medical, dental, vision, 401(k), clothing allowance

• Compensation: $165,000–$185,000 base, plus performance bonus

Apply

Apply at Proper Cloth

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