Working His Way Up: How Jason Freeman Landed a Leadership Role at Wayfair


Jason Freeman began his career in product management at small agencies and financial companies. With a bachelor’s degree in industrial computer systems, he had plenty of experience working as a product manager at the director level, but felt something was missing. 

While applying for different product management jobs, Jason noticed gaps in his existing skill set. “I had the product management experience and exposure, but was looking for a more senior role at a bigger company,” he explained. “Without certain skills, like A/B testing and data analysis, I couldn’t go for those competitive roles.” 

When Jason found The Product Management Boot Camp at Texas McCombs, he knew it was just what he needed to get ahead — and eagerly enrolled in the 18-week program. 

Balancing boot camp, work, and side businesses

For Jason, juggling several different commitments was nothing new. Along with his full-time work as a product manager, he also ran two successful side businesses — a software consultancy and an online backpack shop — all while participating in the boot camp.

“I probably spent at least six hours each day on Friday, Saturday, and Sunday working on boot camp projects,” he said. “It was hard to balance everything, because jobs at my level are very demanding.” 

Ultimately, Jason credits his success to determination and dedication. “I committed a lot of time and effort into reading the modules to help myself stay ahead of the coursework,” he said. “It wasn’t too difficult, but it just took time. I wanted a good grade, so I had to commit more time and effort to actually earn an A. That’s what it really came down to.”

Well on his way to Wayfair

Today, Jason’s hard work has clearly paid off — and he’s now an Associate Director of Product Management at Wayfair

Getting here wasn’t easy. Jason went through several rounds of interviews with a hiring manager and panel, and completed two case studies on how he would solve problems if given the position, all while participating in the final stretch of the boot camp. 

“I probably spent at least 40 hours preparing for the interview,” Jason said. “There were questions about my approach to product management, how I manage people and my leadership skills, as well as different case studies.” 

Looking back, the hard work was well worth it. Jason now uses tools he learned about during the boot camp in his daily operations at Wayfair and has a completely new understanding of how people approach product management. 

“The way people view product management and problem solving is very different depending on their background,” Jason said. “You can take different paths to solve the same problem — you don’t necessarily have to take an engineering approach.” 

He also learned to be more empathetic toward others and their viewpoints, and to imagine himself in their shoes. This will allow him to connect with customers more and understand what they’re driving toward. “If I can really build those connections, I will be a more successful product manager because I’ll be able to speak to someone’s point of view better,” he said. “It will be a deeper connection with the customer and stakeholders will trust my opinions and recommendations.”  

Encouraging others

Having experienced the benefits of the boot camp firsthand, Jason highly recommends the program to others who are eager to upskill or advance their careers. 

“It may help you land the job you’ve always wanted, and help you really succeed,” he said. “Sign up sooner rather than later. If I knew about this opportunity five years ago, who knows where I would be today.” 

Why wait? Get started with UT Austin Boot Camps to improve your skills in coding, data analytics, product management, UX/UI, digital marketing, and cybersecurity.


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