C. Justin Whitaker, Esq.
A lawyer who understands how to build companies the right way, having spent his career inside the c-suite.
Justin Whitaker is a Tennessee-licensed attorney and Chartered Property and Casualty Underwriter with nearly twenty years of experience building legal and operational infrastructure inside fast-growing companies. He has served in multiple c-suite and managing executive roles, including as general counsel. He's the lawyer a founder calls when the company is too big to run on handshake agreements but not yet big enough for a legal department of its own.
Most recently, Justin spent close to six years as the founding legal and operating executive inside three venture-backed insurance technology firms. He joined Koffie Financial as its second employee, building the legal, compliance, and underwriting foundation of a data-driven commercial trucking MGA from the ground up. He went on to serve in similar founding roles, including as chief risk officer and later as chief operating officer at two additional venture-backed insurtechs, drafting and negotiating carrier agreements, producer contracts, and technology vendor arrangements while managing outside counsel from the inside.
That pattern built on an earlier foundation. Justin began his legal career as a litigation attorney at Leitner, Williams, Dooley & Napolitan, representing several Fortune 100 companies in Tennessee state courts and the Sixth Circuit. He later served as regional counsel and underwriter for Great West Casualty Company, one of the country's largest commercial trucking insurers, where he earned the CPCU designation, the terminal professional credential in the property and casualty insurance industry. Between litigation, underwriting, and the executive suite, he's seen how companies get built well and badly, from the inside.
Justin is licensed to practice law in Tennessee state courts, the United States District Court for the Eastern District of Tennessee, and the United States Court of Appeals for the Sixth Circuit. He received his Doctor of Jurisprudence with a Concentration in Advocacy and Dispute Resolution from the University of Tennessee Winston College of Law.
Clear enough to act on, thorough enough to hold up.
Justin has drafted the fifty-page memo when the stakes demanded it, and the two-page summary when a founder needed an answer before a call started in ten minutes. Neither is the lesser skill. The real test of legal work isn't whether the document sounds impressive, it's whether the client understands the risk, sees the options, and can actually act. Every contract, memo, and recommendation out of Whitaker Legal Solutions is built to survive scrutiny and to be genuinely useful to the person who has to live with it.