A Beautiful Day in the Neighborhood

Michael Cruz ('02) helps fuel the ascent of Trunk Club with a mixture of technological expertise, entrepreneurial drive, and customer focus

As a child growing up in Guam, Michael Cruz (’02) became fascinated with the manufacturing process while watching Mister Rogers’ Neighborhood.

Michael Cruz ('02)“Mr. McFeely, the Neighborhood mail carrier, would play a videotape showing how something was made, and I would be amazed at how everyday things could be created automatically,” Cruz says.

Fast forward to his days as an industrial engineering major at Northwestern, where Cruz’s fascination with process intensified as he embraced courses on logistics and optimization.

Today, Cruz has parlayed his childhood fascination and undergraduate studies into an executive role at the personal shopping service Trunk Club. There Cruz blends his technical acumen and earnest entrepreneurial spirit to help fuel Trunk Club’s evolution as a powerful retail brand. The Chicago-based service connects customers with a personal stylist, who ships them a selection of handpicked clothing. Customers then have 10 days to decide what to keep and what to send back.

“I’ve learned that as much as I love programming and processes, I love building teams and companies even more,” says Cruz, Trunk Club’s vice president of engineering.

That self-realization began taking root at Northwestern.

An engineering entrepreneurship class with Professor William White ignited Cruz’s deeper passion in business. Along with two fraternity brothers, Cruz launched his first entrepreneurial venture, a DVD rental store at the Norris Center on the Evanston campus. Although the enterprise eventually withered in the shadow of Netflix, Cruz relished the experience.

“Anytime you have ambiguity, that’s the fun,” Cruz says. “That’s when you learn a lot about yourself and what it takes to thrive.”

Anytime you have ambiguity, that’s the fun. That’s when you learn a lot about yourself and what it takes to thrive.
—Michael Cruz, vice president of engineering, Trunk Club

In fact, it was the prospect of ambiguity that encouraged Cruz to apply to Trunk Club’s job posting on Craigslist that simply read, “Engineer.” Intrigued by the company’s prospects, and even more by its people, Cruz joined Trunk Club in November 2011 as its first engineer.

At the time, the two-year-old company was struggling to secure stable footing. The company had only a few dozen employees and, according to Cruz, “nascent” technology. 

Cruz immediately set about to elevate Trunk Club. He led several iterations of technology to arrive at the current user experience, learning how to apply innovative retail and e-commerce models to IT, how to deal with post-merger integration following Nordstrom’s 2014 acquisition of Trunk Club, and how to hire and motivate a growing technology team, which now numbers 70.

And he accomplished it all while maintaining Trunk Club’s signature brand of personalized service. “Even while we’re scaling, the customer relationship has to feel rich and personal, and that makes for a massive technical challenge,” Cruz admits.

Though he faces a multi-faceted and complex challenge, touching everything from the user interface to supply chain, operations, and finance, Cruz has embraced that challenge and stands as a key player in Trunk Club’s continued development. The company now employs more than 1,300 and has been growing steadily year over year.

“It’s exciting to know I played a role in helping Trunk Club get here,” Cruz says.

Mr. McFeely would be impressed.