Wendy Pyne

Wendy Pyne entered the financial services industry in 2003, helping small- and medium-sized businesses craft life, disability, and health benefit packages for their employees.

Then came the financial crash of 2007-2008, and Wendy had a front-row seat to the chaos. She watched as many of her clients saw their portfolios take a nosedive and decided they’d rather buy dental insurance than contribute to their 401(k)s—even with a company match. It became painfully clear: America had a financial literacy problem, and something had to change. Determined to make a difference, Wendy built her investment philosophy around risk management. Her mantra? Losses hurt more than gains help. She’s made it her mission to help clients protect and grow their assets while offering the education they need to avoid future financial potholes. Wendy’s passion for helping people prepare for retirement has led her to years of continuing education and an insatiable quest for creative solutions. She’s all about finding those unique financial tools and strategies that leave her clients saying, “Why didn’t anyone tell me about this sooner?” But Wendy doesn’t stop there. She’s a serial volunteer and community builder. As Managing Director of the MetroWest chapter of Polkadot Powerhouse—a women’s international connection group—she fosters meaningful connections. Her resume of service includes stints as President of the Ashland Business Association, Vice Chair of the Ashland Emergency Fund, and a board member for the Ashland Education Foundation. In these roles, Wendy has worked with local business owners, schools, and residents to deliver innovative programs and financial aid, especially when her community needed it most. When she’s not in the office or giving back to her community, Wendy’s home life is, shall we say, delightfully chaotic. She and her husband share their home with chickens, cats, and kids (the order of priority depends on the day). Wendy’s hobbies are as varied as her financial strategies: practicing French, traveling, hiking, canoeing, camping, reading, weightlifting, and museum browsing. She’s passionate about her job, her family, her friends, and her pets—and she finds inspiration in all the twists and turns life throws her way. Whether it’s a family adventure or a new way of thinking, Wendy is always ready to dive in. It’s this openness to experience that fuels her drive to help her clients navigate the financial world with confidence and a smile.