Josh Lee-Masiello

Meet Josh Lee-Masiello

WinterWyman Josh Lee-Masiello

Josh Lee-Masiello

Lead Associate
Executive Search




Joshua Lee-Masiello, a Lead Associate with WinterWyman Executive Search, is 100% focused on the right career move for his executive candidates and aims to be that confidante they depend on for sound and honest career advice. Josh takes pride in learning how client opportunities can best suit his candidates’ long-term career strategies. When it comes to his business relationships, he’s in it for the long haul and has established himself as a trusted advisor and career coach for the executives he represents. When it comes to working on the WinterWyman Executive Search team, he says “it’s rare to work on a team as cohesive, dynamic and supportive as ours.” Josh has had an integral part in successfully completing many executive and C-level searches, including: the CFO for Community Counseling Services; the Executive Director of Business Development for Estee Lauder; the VP / Controller for ClassPass; the VP / Controller for Medidata and the VP Finance & Accounting for Orchard Platform.

Josh has a Bachelor's degree in Business with a minor in Human Resource Management from Saint Anselm College where he was part of the Delta Epsilon Sigma Chapter & Omicron Delta Epsilon Chapter of the National Honors Society. When Josh is not advising his candidates, he is a TV/movie buff and an avid world traveler. He's also an Afterschool Coordinator for the Bishop O’Neil Center and a volunteer at the Greater Boston Food Bank.


“I worked with both Jon Mazzocchi and Josh Lee-Masiello and they were great. From prep calls before every interview/meeting/call, to status updates and letting me know what the … Read more