group photo of the Winston Financial team

A Family Firm Based in Madison, Wisconsin

The team behind Winston Financial

We’re here to help people in Wisconsin pursue their dream retirements.

The Heart of Our Firm

We’ll be honest: Winston was the real star of the show around here. Our original Director of First Impressions, Winston ensured every meeting started with a smile. Whether he was greeting clients at the office, making friends at community events or taking a well-deserved break in his favorite chair, Winston brought joy to everyone he met.

Known for his love of belly rubs, his eagerness to dress up and his trademark grumpy-but-lovable expression, Winston had a special knack for making everyone feel right at home. While we miss him dearly, the welcoming atmosphere he created remains the heart of our firm.

Today, Winston's trusty apprentices, Mabel and Walter, have stepped up to fill some very big paws. They spent years learning from the best, and they are fully committed to carrying on Winston’s legacy.

They are dedicated to building lasting relationships and making sure you feel like a part of our family the moment you arrive. They are ready to welcome you, just the way Winston taught them.

small white and black dog who is not actually Winston

The Winston Financial Team

Winston Financial logo

Jason Craig

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Founder | Wealth Advisor

Jason Craig

I help retirees plan long, successful retirements with strong income plans, tax strategies, market-safe growth, and plans for "what if."

I help all families, whether working or retired, protect their future with financial strategies that provide cash benefits, tax advantages, guarantees, and peace of mind. As an independent advisor and broker, I work for you — not for the insurance companies.

Cindy Kiley-Craig

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Founder | Medicare Specialist

Cindy Kiley-Craig

I help people navigate the confusing world of Medicare and Health insurance, making sure you have the right coverage in place without overpaying. Not only will I get you the best coverage, I'm your local rep ready whenever you need me.

Maria Sundsted

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Senior Benefits Advisor 

Maria Sundsted

Bio coming soon!

Patrick Schmidt

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Senior Benefits Advisor 

Patrick Schmidt

Before becoming a retirement advisor, Pat spent four years as a left-handed pitcher in American Minor League Baseball. He now uses the discipline and focus he honed in the professional baseball to help his clients pursue their financial goals.

Pat has a passion for guiding individuals toward personalized retirement solutions. With a strong foundation in finance and education, he has dedicated his career to simplifying complex financial concepts and empowering people to take control of their financial futures.

As the host of the On-Track Retirement Show, Pat combines his expertise with a relatable, coaching-driven style that resonates with listeners.

Persephone Caulkins

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Executive Assistant

Persephone Caulkins

Bio coming soon!

Next Step

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