Alumnus turned top Seattle tech CEO tackles health care arena

Contact: Amie Heasley
A portrait of Rajeev Singh.

Rajeev "Raj" Singh, BS '91, founded Accolade in 2007.

SEATTLE—While Rajeev “Raj” Singh, BS ‘91, may not have been the shining star on his high school football team, he’s shown brilliance as a CEO that surpasses bursts of speed or agility.

Seeing the best in people may be this engineering grad’s greatest strength.

“If people believe you care about them because you do, and they understand you’re willing to make the same sacrifices, that you don’t put yourself above them but amongst them,” the tech icon and one of the top CEOs in the country adds, “they’ll do a lot for you.”

An avid sports fan, Singh didn’t land his childhood dream job as the quarterback for the Detroit Lions. Today, he’s leveling the health care field as the CEO of Accolade. 

Founded in 2007, Accolade combines virtual primary care, mental health support and expert medical opinion services with intelligent technology and best-in-class navigation. Under his leadership, the company went public in 2020 and integrated four companies in over $1 billion in acquisitions.

Singh’s journey to becoming a leading CEO wasn’t linear though.

In fact, Singh stumbled at the first college he attended. “GMI (Kettering) wasn’t a good fit,” he admits. “I was miserable, so at 18 years old my choice to deal with my misery was to rebel, not to go to class, just to screw up.”

Fortunately, his father, Gopal, recognized his son’s unhappiness and encouraged him to seek greener pastures closer to home in Kalamazoo. A first-generation immigrant, Gopal came to America to further his education and forge a better life for his growing family.

Singh has not only said that WMU “saved his life,” but he also credits the now-chair of the Department of Industrial and Entrepreneurial Engineering Management for nurturing his lofty ambitions.

“When I arrived at Western, I decided it was time for me to start my life over,” he says. “So, I basically begged Dr. Azim Houshyar to let me take 25 credits in one semester.”

Houshyar approved the request despite worrying Singh might be swinging the pendulum too hard.

“There are moments in your life where somebody can close or open a door,” Singh says. “You look back and you remember the people who do these things. And as you get later in your life, you want to be one of those people, too.”

“I don’t think a lot of professors would have been so invested or checked in so often, especially not for some random kid who came in looking like a college dropout,” he continues.

Experience-driven learning also gave this Bronco business acumen and insight into what separates thriving companies from struggling ones. As an engineering student, Singh had the opportunity to visit manufacturing plants across West Michigan, including Haworth and Eaton Corporation, where his father worked as an engineer.

“I walked through some places and thought, ‘Oh, these guys are pretty attached to the way things used to be,’” he says. “Then I saw forward-looking companies, like the furniture companies in Western Michigan, that would go on to have great success.”

Leaping beyond his comfort zone  

After graduating, Singh went to work at Ford Motor Company but quickly learned the job didn’t feed his entrepreneurial spirit. He left Ford and was admitted to law school at Notre Dame.

Waiting to start school, Singh’s older brother Steve then called one day with an exciting proposition: Join him and another up-and-comer Mike Hilton in San Francisco to write code and create what later became Concur Technologies, a travel and expense management company.

Taking advantage of Seattle's lower cost of living, they relocated their fledgling startup and worked out of an apartment. In just seven months, Singh had already burned through his $2,500 savings.  

“You have to have courage behind your convictions,” he says, “because sometimes you may need to bet on your company more than once if you want to grow.” 

That faith, combined with a core team who also doubled down on the company’s vision, paid off. Concur grew to more than $800 million in revenue, over 4,000 employees and more than 25,000 customers before being acquired by SAP AG for $8.3 billion in 2014.

Outside of leading a multimillion-dollar health care tech company, Singh is also a dedicated philanthropist.

Amid the pandemic, he and a group of like-minded community leaders launched All in Seattle, which raised more than $27 million to aid local food banks, small businesses and housing nonprofits. Giving back appears to run in the family, as Singh’s parents opened a school in the village in India where they were born that currently provides about 800 girls from sixth to 12th grade access to life-changing education.

Since Singh’s days on campus, he’s weathered highs and lows and experienced setbacks and triumphs. Through it all, he’s remained grateful for the foundation he built at WMU.

“I may be a mediocre engineer,” he jokes, “but gaining an understanding of scientific methodology and how to frame and solve problems, that’s been critical for me. And I learned much of that from engineering school at Western.” ■