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Keith Kostrzewski

Owner and operator, sideKick. Hilton Head Island, South Carolina.

Keith Kostrzewski owns and operates sideKick. He moved to Hilton Head Island five years ago and found his forever home. He has always been an entrepreneur with a drive to help businesses grow and scale, and he believes there has never been a more equalizing moment than this one: the kind of help that once belonged only to large companies now fits a business of twelve people. He is here to help the businesses in the place he calls home make the most of it, and to see these communities thrive.

His career runs from LEGO to Pearson to the Buffalo Bills, with many stops in between at startups and firms across consumer brands, education, professional sports, B2B and technology, in both executive roles and consulting engagements. He has worked as an analyst, seller, marketer, developer and operator, and has gone from individual contributor to CEO.

Technology was always part of how he saw the edge. At Kellogg, where he earned his MBA, he noticed it early. There were strong practitioners everywhere. What was thinner was a real understanding of how technology could add hours and clarity across a whole business, not just inside one department. For years that view had nowhere to land. Agents changed that. The curiosity across the whole business, the discipline of running operations and the technology layer finally fit together as one practice. That practice is sideKick.

“I do the dirty work on the front end of technology, so you don’t have to,” Keith says. That means sorting the noise, testing what actually works and setting it up on the tools owners already pay for, so they can keep running their business.

In a first meeting, he won’t open a laptop. He’d rather hear about what you built, and he won’t talk over it. “I will not treat the last ten years as a mistake. I will tell you what is leaking. Then we go to work.” And he is clear about his role: “I am the name in the first meeting. I am not the workforce. If this only works when I am in the room, I did this wrong.”

Keith is a former Division I athlete who has run six marathons for charity and served on multiple nonprofit boards. He is a devoted father of three daughters. Those three are why he does this.