Tracy Cashman

Meet Tracy Cashman

Tracy Cashman

Tracy Cashman

Senior Vice President / Partner
Executive Search
Year started recruiting







Tracy Cashman, Senior Vice President and Partner of WinterWyman Executive Search, positions herself as an extension of her clients during their hiring process and is committed to finding the right talent for each retained search. She has more than 20 years of search experience working with public, private and pre-IPO clients to execute searches in a wide variety of industries with companies including The Baupost Group, EBI Consulting, Best Doctors, Suffolk Construction, Bain & Company, and PC Connection. Tracy’s success is the result of her long-term approach and her deep-seated engagement within the Boston and New York technology leadership communities. In addition to being a brand ambassador for her clients, she sits on the Board of Directors for SIM Boston and has been featured on news programs such as FOX and WBZ and in publications such as CIO and Fortune. Her drive for connecting companies with best leaders mirrors her passion for increasing women’s presence in technology.

Client Work


"It was a great experience working with Tracy Cashman. She was very professional when guiding me through the whole job searching process. I was especially impressed by her … Read more
"I had never heard of or used any type of 'headhunter' staffing firm before and I can honestly say my experience was delightful. I spoke with Tracy Cashman frequently and she kept … Read more
"She treats me like I'm the single most important customer in her very broad portfolio. Of course I believe I am too, so I might be slightly biased or moderately delusional, but … Read more