A Family Firm Based in Madison, Wisconsin

Jason loves watching the confidence grow in the people he serves as they work together to build plans for a lifetime of financial security. Inspired by his wife, Cindy, to leave his corporate job, he found his true calling in meeting directly with families to help them prepare for their futures. Jason specializes in income planning and positioning investments for long-term stability, helping clients make sure they don’t outlive their money.

Before joining Winston Financial, Jason worked as an insurance broker and spent 15 years working for Epic Systems. He earned his bachelor’s degree in business administration and economics from Rockford University, graduating summa cum laude. He operates as a fiduciary and has passed the Series 65 securities exam, plus holds life, health and annuity insurance licenses.

Jason grew up on a farm and has called Madison home for over two decades. He shares his life with Cindy, their three children — Lucas, Elanor and Eve — and the family’s French bulldogs: Walter, Mabel and the always remembered Winston, the firm’s namesake. Outside the office, Jason enjoys dating his wife, spending time with his kids and reading books. He is also drawn to Irish and Scottish culture and proudly serves as the President ofMadison’s best club, the Single Malt Society of Madison.

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Beginning her career as a registered nurse, Cindy has always been driven by a deep desire to help people. She transitioned into the financial industry in 2013 after hearing a young business owner share how the right health, disability and life insurance allowed him to spend his final months focused on his family, rather than worrying about finances after he found out he had terminal cancer. That moment inspired her to help others avoid that same worry.

As the founder of Winston Financial, Cindy believes everyone deserves an insurance plan that fits their individual needs. She uses her nursing background to better understand clients’ medical situations, guide them toward the right coverage and connect them with additional resources and support systems. She loves taking the time to understand clients’ full situations, including their goals, and tailoring an approach just for them so they can leave feeling confident, supported and well cared for. She holds life, health and long-term care licenses.

Cindy lives in Madison with her husband, Jason, who works as Winston Financial’s retirement specialist. Together, they have three children: Lucas, Elan or and Eve. The family also loves their three rescued French bulldogs, Walter, Mabel and the late, great Winston. Winston Financial is named after their beloved dog, who could often be found snoring on his bed in the office while Cindy was meeting with clients.

Outside work, Cindy enjoys reading, cooking, focusing on healthy living and taking ballroom dancing lessons with Jason. The entire family also loves to travel. Cindy is passionate about giving back to her community in many ways, including volunteering with Zeteo, a local non profit that builds housing for survivors of sex trafficking, as well as Morgan’s Caring Connection, which helps families establish special needs trusts for their children.

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Maria’s decision to become a Medicare and retirement benefits advisor was inspired by her family’s struggles to navigate health insurance during her mother’s cancer treatment. When her parents later faced costly penalties due to poor Medicare guidance, she knew she wanted to help others avoid those same hurdles. Today, Maria loves helping clients understand complex health care decisions and feel confident as they step into retirement.

Before joining Winston Financial, Maria spent a decade working as an occupational therapist. She earned her master’s degree in occupational therapy from the University of North Dakota in 2015. Maria is certified in long-term care planning and by America’s Health Insurance Plans (AHIP), and she holds health and life insurance licenses in Wisconsin and Illinois.

Maria grew up on her family’s farm in Montana as the youngest of three and still enjoys visiting whenever she can. She’s called Wisconsin home since 2015 and currently lives in the Madison area with her partner, his daughter and their two cats, Charlie and Beasley. Outside of the office, Maria stays active through weightlifting, yoga and taking classes at the Madison Circus Space. She also loves spending her free time cooking meals for her family and friends.

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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 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.

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A great client experience begins with a welcoming environment, and that is exactly what Persephone strives to create. From thevery first interaction, she helps make clients feel informed, supported andconnected.

Persephone has made a career out of making people feel comfortable. Before joining Winston Financial, she spent more than eight years working in wellness as a licensed massage therapist and physical therapist assistant. She managed client relations and social media for a massage therapy business, combining communication, organization and creativity to strengthen both client experience and daily operations. This experience now defines Persephone’s approach to client experience.

A Madison, Wisconsin, resident, Persephone values family,creativity and continuing to learn. She stays active through fitness, flowarts, camping, hiking and traveling. She also enjoys music and spending timewith friends, family and her Pomsky, Sammy.

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