Jeff Judge, CFP®, AEP®, ChFC®, CLU®

Managing Partner

Trusted Guide for Busy Professionals Seeking Financial Clarity

“You don’t need to do this alone. I help clients cut through the noise, avoid costly mistakes, and make confident decisions even during life’s biggest transitions.”

Meet Jeff – Steady Hand in Unsteady Times
Jeff didn’t grow up around wealth. His parents were blue collar and did what they could to make ends meet. When his dad got sick, Jeff worked multiple jobs in high school and college to help the family stay afloat. That experience taught him how stressful money can be when you don’t have the right support and it lit the fire for his career in financial planning.

Today, Jeff is one of Chesapeake’s founding partners and a go-to advisor for professionals navigating complex transitions like retirement, business sales, or sudden windfalls. With nearly two decades of experience, he’s known for delivering calm, clear guidance when it matters most. Clients say working with him feels like talking to a longtime friend, if that friend happened to be an award-winning financial expert.

Credentials You Can Trust
Jeff holds multiple advanced designations that reflect his commitment to excellence:

  • CERTIFIED FINANCIAL PLANNER (CFP®)
  • Chartered Financial Consultant (ChFC®)
  • Chartered Life Underwriter (CLU®)
  • Accredited Estate Planner (AEP®)

He’s also a multi-year Five Star Wealth Manager Award recipient (2014, 2017–2026) and has led retirement and financial education workshops for Fortune 500 and mid-sized companies across the Baltimore and DC metro areas.

The Method Behind the Calm
Jeff leads clients through Chesapeake’s R.U.D.D.E.R. Method™, a simple yet powerful process for turning financial chaos into confident action. Whether you’re facing a big life shift or just want to feel in control again, Jeff combines empathy, expertise, and accountability to get you there.

Outside the Office
Jeff lives in Forest Hill, MD with his wife, Courtney, their son, Reed, and their three dogs Ash, Twix, and Blue. He’s a passionate home cook, lover of live music, stand-up comedy, and comic book movie buff who can just as easily be found on the sideline of Reed’s soccer games, watching live sports in person or on TV, or quietly meditating. If you’re a Disney fan or soccer junkie, you already have something to talk about.

Ready to Feel More in Control?
Jeff and the Chesapeake team are here to make your financial life simpler, more strategic, and a whole lot less stressful. Book a Fit Call to see if we’re the right guide for your next chapter.