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Jack McCloskey

Chief operating officer, Vintage Financial Services

When Jack McCloskey talks to people about their finances and sees the tension melt their faces, he knows he’s doing a good job. “I’m not a doctor, but I can reduce somebody’s stress and hopefully make their life better,” he said, “and that’s really rewarding.”

McCloskey joined Vintage Financial Services 11 years ago, just out of college, as a financial planner. At the time, the firm had about 200 clients and six employees. Today, the business has grown to around 550 clients and 16 employees. McCloskey’s role has grown alongside the firm, and as partner and chief operating officer, he manages the financial advisers and oversees day-to-day operations. He relishes mentoring his team, while also encouraging them to learn from one another. “We have a wonderful staff,” he said. “Watching our staff grow and accomplish their personal goals, that’s huge.”

Outside of work, McCloskey’s immersed in the Ann Arbor community, whether he’s volunteering with his wife, Ashley, at craft beer festivals with Michigan Brewers Guild; or weighing in on urban planning, as he did in his former role with the nonprofit Building Matters Ann Arbor.

“It’s nice to meet new people and explore how to make our community better,” he says.

— Kate Silver