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Unretirement Party

Former President and CEO of Seaway Bank and Trust Company EVP and President of Wealth Management-Illinois for the Northern Trust Company
Joined Vistage in 2007
Vistage Chair since 2019
Darrell (left) congratulates founding member Tom Masiewicz’s 5-year anniversary with Vistage.

In 1999, I had been in banking for nearly 20 years and was a leader at Northern Trust when I pursued my MBA from the Kellogg School of Management. It broadened my perspective on business and leadership. The intellectual stimulation — I wanted to continue experiencing that.

Elisa Spain, a former Northern partner who left to start her own Vistage group, called me while I was at Northern and described the value proposition of Vistage. She signed me up on the spot, and I spent 10 years in her group.

Toward my last three years at Northern, we put 40 leaders through three Vistage Inside groups. That’s where I got excited about coaching and mentoring.

But, as I contemplated retirement from Northern, I explored different opportunities. I became the CEO of Seaway in 2014, the third-largest African-American-owned commercial bank in the country. This was an opportunity to see if I could help a bank that had run into trouble.

There was constant pressure. We would have as many as 18 regulators in the bank, scouring our books. But for me, it was a great experience. We restructured the bank’s balance sheets, increased our liquidity position, and improved our tier-one leverage ratio. The following year, I became the first African-American chair of the Illinois Bankers Association.

What was not a success: My vision was to transform the bank from a solely brick-and-mortar strategy to a digital strategy with fewer physical facilities, selling or exiting nine of the bank’s 13 branches and redirecting the capital into technology. The majority owner had different ideas. I realized that I would have difficulty executing a strategy that required legacy banking. So, after 15 months, I re-retired.

Now I serve on four boards and lead a Vistage Chief Executive group and a Key Executive group, and I serve as the Best Practice Chair for the Bay Area. It has become a calling. I talk from actual experience of going through down cycles, forced reduction and perilous times. And being a Chair allows me to cultivate that curiosity that I developed back in the late ’90s.

Will I retire a third time? Why retire when you’re having fun?

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Life After the Sale