Overview
When a business is in the kind of trouble that keeps owners up at night, the kind of trouble where one engagement decides whether the company survives, they don’t want a lawyer who quotes case law at them. They want someone who has built a company, fought for one, and knows what an operator actually feels at 11 p.m. on a Tuesday. That’s why businesses call Charlie Jimerson. That is the lane Charlie has occupied for over two decades.
Charlie is the Founder and CEO of Jimerson Birr, the Florida-based business law firm he built around an unfashionable idea: that lawyers should make their clients’ lives easier, not more expensive. He acts as outside counsel for businesses of every size, getting deals over the line, leading high-stakes litigation teams, advising executives and boards through pressure moments, and stepping in personally when the wheels start coming off. Two decades into the work, the categories of business problems that still surprise him are running out, as he has cleaned up just about every kind of mess a Florida business can get into.
The credentials behind Charlie’s name do work most lawyers’ credentials cannot. They tell you he was recognized early, when peer-reviewed programs (Best Lawyers in America, Super Lawyers, Florida Trend Legal Elite, 40 Under 40) identified his ability long before he had a firm to lead. They tell you he proved it again as he built and led Jimerson Birr to year-over-year recognition as one of the fastest-growing law firms in the country (Law Firm 500, Gator100, JBJ Fast 50) while simultaneously being named one of Florida’s Best Places to Work and a U.S. News Best Law Firm, a combination that growth-stage law firms almost never produce. More recently, the recognition has shifted toward distinction-tier honors that reward sustained career achievement: 2025 Jacksonville Business Journal Ultimate CEO, 2025 GrowFL Florida Companies to Watch, PS27 Veteran Entrepreneur of the Year Finalist, Law.com Legal Innovator Award Finalist, America’s Top 100 Attorneys Lifetime Achievement Award, and The Business Journals’ Top 100 Most Influential Attorneys in Law and Business in the United States. This arc means something specific for clients. Charlie has been doing this long enough to have seen most of it before, built the systems and the team to deliver consistently rather than heroically, and been measured against the best in his profession and the best in business and held his ground in both.
What clients remember, though, isn’t the trophy case. It’s the way Charlie attacks a problem: pragmatic, competitive, business-first, quick on his feet, and equipped with a sense of humor that keeps tense rooms from turning toxic. He thinks like an owner because he is one. When growth companies and executives need a business lawyer who can handle pressure, deliver outcomes, and translate legal risk into business decisions, they call Charlie.
Practice & Client Focus
Charlie represents owners, executives, and growth companies as their strategic advisor first and their business lawyer second. Most clients use him the way they’d use a high-functioning general counsel: he handles the contracts that run the business, the disputes that show up uninvited, the deals that need to close, and the bet-the-company moments that keep founders awake at night. What executives actually pay him for, though, is what sits underneath the legal work. They pay him to think with them, see around corners, and help them make better decisions about strategy, risk, people, capital, and timing. They pay him to be a peer in the room.
He is the lawyer growing businesses call when they need someone who can handle whatever shows up next. Some days it’s a lawsuit. Some days it’s a deal. Some days it’s a workout, a key relationship at risk, a difficult termination, a regulatory inquiry, a lender getting nervous, or a competitor hiring away key personnel. Charlie has spent more than two decades doing all of it, and Jimerson Birr is built to deliver it without the unpredictability that makes outside legal services feel like an unmanaged expense.
His clients tend to share a profile: they are running real businesses, they have something to lose, and they want a lawyer who can think with them about strategy, risk, leverage, and outcome rather than billing them through a problem. The clients he serves best often have four things in common: real revenue, real risk, a desire for clear answers, and an allergy to legalese.
About Charlie
Charlie is a native Floridian with family roots in the state going back to its earliest days. He grew up in Sarasota County working summers for his grandfather’s plant nursery, supervising landscape crews, and running shifts before he could legally drive. After high school, he enlisted in the United States Air Force to serve his country and pay for college. While on active duty as a Combat Meteorologist supporting worldwide operational missions, he became the youngest operationally certified meteorological forecaster in U.S. Air Force history and was named Airman of the Year. He simultaneously earned his B.B.A. summa cum laude from the Lundy-Fetterman School of Business at Campbell University and graduated in the top 2 percent of every academic program he attended before law school.
He earned his Juris Doctorate from the University of Florida Levin College of Law, where he held leadership roles in several student organizations and studied internationally through the London Legal Consortium, where he also met his wife, Ashley. He built his early career across a broad range of business law disciplines, including commercial litigation, construction, real estate, banking, and corporate matters at established Florida firms before founding Jimerson Birr and building it into the firm it is today.
Beyond Jimerson Birr, Charlie owns and operates additional businesses across real estate, technology, financial services, professional services, and hospitality industries, giving him direct, ongoing experience with the operator decisions his clients make every day. The arrangement is deliberate. Running real businesses keeps his advisory work grounded in what actually moves the needle for owners and executives, not what reads well in a memo.
Outside the practice and the entrepreneurial grind, Charlie has served on more than 60 professional, civic, and philanthropic boards across Jacksonville and the state of Florida, where he stays actively involved in business, legal, veteran, and community organizations he believes in. He has also coached 34 seasons of youth sports across football, baseball, soccer, and basketball – a stat his wife describes as either heroic or a personality disorder, depending on the season.
Charlie lives in Ortega with Ashley, their two children, and their two Italian Greyhounds, Olive and JoJo. His free time is limited, and he spends most of it doing one of the following: yelling at SEC football games while trying to keep the cuss words in; traversing the country watching his son play nationally competitive travel lacrosse against teams whose parents take this all very, very seriously; serving as a UFC-appointed MMA media correspondent; traveling to remote places with an ambitious and overcomplicated itinerary; participating as the deputy detective for all of his wife’s true crime case cracking; grilling meats; lifting weights with the misplaced confidence of a former athlete; walking the kind of distances that have begun to alarm his neighbors; ranking just about anything in a top-ten list; apologizing to his wife for reasons unclear even to him; taking his kids to concerts he has no business attending; hunting down dive bars with good jukeboxes; eating oysters in daylight hours; throwing impromptu living-room dance parties; and running a fantasy cut-throat football league he treats with the seriousness of a federal case.
What clients hire Charlie to do:
- Sit at the executive table as a trusted business advisor, not just a legal one
- See the business issue underneath the legal issue, and address both
- Translate legal risk into business decisions leadership can actually act on
- Negotiate, structure, and close the deals that move the business forward
- Defend the bet-the-company moments
- Resolve the disputes the business can’t resolve internally
- Provide ongoing general counsel without adding in-house headcount
- Deploy the right specialist when the work calls for one
- Draft and enforce the contracts that run the business
Charlie works at the altitude where business problems and legal problems converge, a place most lawyers can’t see from. Jimerson Birr is built around specialists who go deep in their lanes: construction, real estate, financial services, healthcare, hospitality, technology, professional services, and more. Charlie’s job is to stay high enough to see across all of them, lead the matters where executive judgment and strategy matter most, and put the right specialist on the right problem when technical depth is what wins.
When clients want predictable access at predictable cost, the firm’s Longevity Legal Plans deliver a fixed-fee outside general counsel relationship with defined service levels, designated team coverage, and direct access to Charlie.
When clients ask for a strategy, he gives them one. When they ask whether to dig in, he tells them the truth. When clients need peace of mind, he gives them what most lawyers can’t: a plan they can execute, a team they can rely on, and a peer they can trust. He becomes a part of the business that they no longer have to think about.