Roy Gilbert

Dennis Clarke learned how to run a real estate firm on-the-job

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Title : CEO, Cummings Properties

Age : 51

Residence : Winchester

Education : B.A. in American history and literature, Harvard University, 1990

Dennis Clarke graduated Harvard University 30 years ago with a liberal arts degree, an interest in real estate and no clear path to a career.

After a few stints in sales in other industries, he approached several CRE firms looking for a job. Bill Cummings agreed to see him and offered him a job in sales at a local newspaper he’d recently started. After growing that and several other titles to profitability, they were acquired. By 1995, Cummings knew Clarke was a good fit for his brand and brought him aboard to run the Cummings property management business.

When they put him in charge of the property management group, Clarke had management experience, but no real estate experience. He had, however, learned the way this company manages businesses. Surprisingly, he picked up the real estate business from the people around him, who seemed happy to teach him what he needed to know.“Here I was in my mid-20s, and most of the people I was working with were 10 or more years older than me with more real estate experience, but they were willing to teach me the ropes,” Clarke said. “It was on-the-job-training with a lot of diversely talented people who just knew we’d all be better if we worked together.”By 2004, Clarke had worked his way up to company president and CEO. And while he’s proud of […]

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