Director of Sales (New York)

Our Vision:

Trumaker is building a new kind of men’s apparel brand that delivers exceptional quality apparel through a personalized shopping experience powered by technology and a distributed workforce of trusted style advisors, called Outfitters.

Here’s how we're doing it:

To create the best product experience, we own it every step of the way. We design every product at our San Francisco-based headquarters and work directly with the best producers in the world to develop products you won’t find anywhere else. Through our team of Outfitters, we build and nurture individual relationships with all of our customers in order to deliver personalized style and fit that makes them look great and feel more confident than ever.

The Role:

You will lead the development and growth of Trumaker in the greater New York area. You'll be given the framework and autonomy needed to recruit, train and develop a productive team of Outfitters who build the Trumaker brand locally through lasting customer relationships, top-notch service, and our exceptional product line and fit. You will be responsible for creating an engaging team culture and a path for success for your Outfitters through group and one-on-one coaching, field training, goal-setting, and consistent development opportunities. Your role will include communicating and training Outfitters on new products and programs as well as providing consistent feedback of key learnings from the field to the HQ team.


  • Direct a team of Outfitters who are sales-focused, passionate about delivering great client service, and driven to succeed through 1-1 coaching methods, goal-setting, field rides, and skills-based training
  • Consistently recruit new Outfitter talent to build a team of top performers through personal referrals and networking
  • Provide consistent training and development of core Outfitter skills, including consultative selling, personal styling, product knowledge, lead prospecting, and clienteling
  • Identify and develop sales leaders by being actively connected to your Outfitters — proactively coach and mentor top performers
  • Consistently track and manage individual Outfitter and team performance metrics through company dashboards and reporting tools
  • Partner with the sales leadership and executive teams to contribute growth-oriented ideas and gain additional training to help increase the results of your territory
  • Create a success culture within your territory, which reflects the company’s aspirations and industry-defining standards
  • Build a local client base and a customer experience through your Outfitter team that leads to consistent reorders and referrals


  • Have a robust track record of successful leadership and management of an outside sales team  
  • Are an expert at selling and building a book of business through various prospecting methods and generating referrals
  • Have a deep appreciation for quality clothing and are passionate about a better product and customer experience
  • Are passionate about developing people and care about the long-term success and personal growth of your team members
  • Are tech-savvy—we are developing online and mobile tools that you will know how to maximize
  • Have experience developing a clientele business where it's more about building relationships and brand-believers rather than just making a sale
  • Are self-driven—you take ownership of results and are comfortable working independently/remotely
  • Are highly organized and can effectively manage a large team, business development, and recruiting activities simultaneously
  • Are an entrepreneur and thrive in a start-up environment—you demonstrate patience and resourcefulness, and you're fanatical about helping to build the next world-class brand


  • Base + individual and team incentives

Meet Some of Trumaker's Employees

Michael Z.


As leader of the Technology Team, Michael ensures that customers' digital experiences function seamlessly. He splits his time between designing new products and solving technical issues.

Tessa T.

Founding Outfitter & Mentor

Tessa is a Trumaker brand ambassador in the San Francisco area. She builds relationships with clients and ensures evert customer is satisfied with their built-to-fit apparel.

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