Made-to-Measure Menswear Fitter

Role Overview

Watson’s Hat Shop is one of the last working heritage hat shops in America. We build custom hats by hand on original 1860s machinery, from 100% USA-made materials, for clients that include country recording artists, Netflix productions, and the official equestrian associations of Arizona. We have built a clientele that pays $799 and up for a hat because they care deeply about quality and craftsmanship.

We are building a made-to-measure menswear program inside that same shop, for that same clientele. We are looking for one experienced clothier to own it. We have entered into a partnership agreement with, America’s fastest growing made-to-measure menswear brands. The cofounder and CEO of that business is a co-owner of Watson’s.

This is not a retail associate position. You build the program, you build your book, you run your appointments, and you get paid heavily on what you produce. But you're not on your own: Every day Watson’s gets many visitors who are high-net-worth buyers. You bring the menswear expertise and the closing ability, and we bring the brand, the shop floor, and the captive audience.

The role starts at part-time until the volume is big enough for full-time. It is in-person and on-location at our Cave Creek shop, with some local travel required.

Why Watson’s

You will have a physical home base in one of the most affluent, brand-loyal communities in Arizona: Cave Creek and North Scottsdale. You will work alongside a master craftsman in a heritage manufacturing environment, which is a differentiator no Indochino or Alton Lane rep can claim. You will have a pre-warmed customer base that already self-selects for quality and custom work. And you will have the autonomy and commission structure to build something that is actually yours.

What You'll Do

• Build and own the MTM menswear program from the ground up: client intake process, fabric selection workflow, appointment structure, and delivery coordination.
• Conduct full made-to-measure consultations: full fitting using our advanced process, fabric selection across mills and weights, design customization, lifestyle and wardrobe assessment, and final styling direction.
• Cross-sell actively into the hat clientele: Watson’s existing customers are your primary prospect pool. You will develop the relationship and revenue flows between the two sides of the business.
• Manage your pipeline end-to-end: prospects, appointments, orders in production, delivery timelines, and follow-up schedules.
• Build and maintain client profiles. Document fit history, preference notes, and garment specs so that repeat orders and referrals come naturally from the relationship.

What We're Looking For

• Minimum six months of hands-on experience in made-to-measure or bespoke menswear; Not off-the-rack retail, not alterations-only. You must have personally conducted full MTM consultations and fittings before.
• Ability to build and manage your own client book. If you have never originated your own clients, this is not the right role
• Technical competency in anatomical measurement, pattern adjustment awareness, and garment specification documentation. You do not need to be a tailor, but you need to know what makes a suit fit and why
• Comfortable operating the growth stage of this program.
• Familiarity with western and Americana culture. Our customers are ranchers, horsemen, and high-net-worth buyers in the Cave Creek and North Scottsdale market.

Meaningful advantages:

• Experience working with high-net-worth or ultra-high-net-worth clients in a luxury lifestyle context
• Existing relationships in the Phoenix-Scottsdale affluent men's market
• Experience launching or building a new service line rather than maintaining an established one
• Familiarity with USA-made textiles, heritage brands, or craft manufacturing environments

Compensation and Benefits

Base salary:$50,000-$75,000 base depending on experience and existing book.

Commission: Strong commission on all MTM garment sales.

Growth: First person into the role has the clearest path to program leadership as it scales.

How to Apply

Apply directly on Indeed.

Pay: $50,000.00 - $150,000.00 per year

Benefits:

• Employee discount

Work Location: In person

Salary : $50,000 - $150,000