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Chris Bakes
President and Founder
Entrepreneurial executive with more than 20 years of leadership experience in Sales, Operations, and Business Development. Chris specializes in scaling organizations, driving strategic growth, and delivering high‑performance operational excellence across the insurance and claims ecosystem.
Founding Story / Why Pro Insurance Group Exists
After decades of leading and scaling high‑growth organizations — including building Nationwide Appraisals into one of the largest independent auto appraisal providers in the U.S. — Chris founded Pro Insurance Group to bring a higher standard of clarity, honesty, and strategic guidance to clients navigating today’s complex insurance landscape.
His mission is straightforward: provide a level of transparency, expertise, and client advocacy that’s often missing in traditional insurance experiences.
Career Highlights & Leadership Achievements
Career Highlights
- Grew a national business unit from $13M to more than $40M in revenue — over 200% growth.
- Led four successful acquisitions and integrations, expanding market reach and strengthening capabilities.
- Built Nationwide Appraisals into a national leader managing 115,000+ claims annually, 40+ colleagues, and a network of 1,000+ appraisers.
- Full P&L responsibility for multi‑division operations, overseeing $13M+ budgets and 150+ personnel.
- Proven success working with Fortune 500 executives and guiding organizations through transformational growth.
Professional Philosophy & What Clients Can Expect
Chris brings the same strategic, forward‑thinking mindset that guided his corporate success into every client relationship at Pro Insurance Group. His philosophy centers on:
- Clarity: breaking down complex insurance decisions into simple, confident steps.
- Customization: designing solutions that fit each client’s actual needs — not generic templates.
- Integrity: building long‑term trust, not transactional relationships.
- Execution: combining strategic insight with real‑world operational discipline.
My Personal Story
Born in Hanover Park and raised on hard work, Chris has been grinding nearly full time since the age of 13. What began as a way to help support himself quickly became the foundation of a work ethic that shaped every step of his life. By the time he graduated from Streamwood High School, he was already juggling long hours and big ambitions — and that didn’t stop when he enrolled at DeVry University. Chris worked full time while earning his bachelor’s degree in Telecommunications, proving early that pressure didn’t break him — it sharpened him.
His first big leap came during college, when he joined MCI Worldcom designing fiber networks back when the internet economy was exploding. But life changed dramatically in 2004 with the birth of his twin sons. Fatherhood didn’t slow him down — it refocused him. Wanting to be closer to home, Chris made a pivotal shift into the Fleet Accident Management industry. That move ultimately opened the door to the insurance world, where he found the intersection of challenge, opportunity, and meaningful impact.
In 2010, driven by a mix of ambition and belief in doing things differently, he founded Nationwide Appraisals. What started as a vision quickly became one of the largest independent auto appraisal providers in the country. A decade later, in 2020, he sold the business to Sedgwick — a milestone that validated years of risk‑taking, long nights, and leading from the front.
But beyond the business wins, Chris’s greatest pride is at home. He and his wife of 24 years have built a family grounded in love, humility, and competition — the good kind. Their twin sons are now 21 and play Division I baseball at Illinois State, and their daughter, 17, is graduating high school this year with plans to attend the University of Missouri in the fall.
Chris is a lifelong baseball junkie — a devoted Cubs fan, longtime youth coach, and someone who still gets the same thrill watching his kids play as he did the very first time he stepped on a field. When he’s not working or at a ballpark, you’ll find him with friends, on a pickleball court, or investing in his health and momentum heading into 2026.
His story isn’t one of shortcuts. It’s one of grit, reinvention, family, and the relentless belief that you can build something meaningful — no matter where you start.