WITS director leaves business world behind

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One November day in 1995, Matt Pickering, an associate in public finance at EVEREN Securities (formerly Kemper) walked into Jenner Elementary School for the first time. EVEREN had just become the first corporate partner of Working In The Schools, and Pickering was one of 20 employees who committed to a year of tutoring at the Cabrini-Green School.

Eight months later, Pickering, 26, decided to kiss the business world good-bye and devote himself to WITS instead. Wanting to increase the number of corporate partners, WITS persuaded him to become its executive director.

“I was happy at EVEREN and am pretty sure I could have continued my career there, but being at Jenner Elementary changed all that,” he says.

“I was with a 1st-grade class, and I really got to know those children good,” Pickering explains. “After a few months, I didn’t even have to be told by the teacher what I should work on with them because I knew them academically. I also got to know them personally, and they got to know me. Sometimes all they wanted to do was talk to me and tell me about their day before they could even think about reading and math.

In time, Pickering says, he realized, “This is important.” When Jenner’s principal and teachers confirmed that importance, Pickering says, he couldn’t say “no” to the WITS offer—even though he was on the verge of another major life change.

At the time, Pickering was a month away from his wedding. “Let me tell you,” he says with a laugh, “when you’re in the middle of planning a wedding for 200-plus people and you spring this kind of news on your fiancé. Let’s just say she was a little nervous.”

In effect, Pickering was joining the family business. His father, Dan, teaches computer science and social studies at West Ottawa Public School in Holland, Michigan, where Pickering grew up.

“I was always in my dad’s school, playing in the gym or helping him on some kind of project,” he says.

Matt’s wife, Nancy, received her certification in elementary education and is working on a master’s in reading and learning disabilities at DePaul University; she is co-teaching at Francis Parker School, an elite private school. She did her student teaching—working with autistic 2nd- and 3rd-graders—at Agassiz Elementary, a public school in Lake View.

“In June, she’ll be finished and looking for a job in either a public or private school,” says Pickering. “I’m pushing her to teach in a public school.” Meanwhile, he has returned to tutoring after a year’s hiatus; he works with 3rd-graders, sometimes one on one or as a group at Byrd Community Academy in Cabrini Green.

In his first 16 months as director at WITS, Pickering lined up 19 corporate partners, and helped launch a WITS pilot program in Denver when corporate partners EVEREN and United Airlines expressed an interest in expanding to their other offices.

“Matt is totally committed,” says Jenner Principal Sandra Satinover. “With his corporate background and actually having been a volunteer, I think he is perfect for the [WITS] job. He’s been outstanding, simply outstanding.”