Brian Cressey

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Brian Cressey

Senior Consultant

Brian Cressey is a Senior Consultant for PlanPILOT. He has spent his entire career (over 30 years) working with qualified retirement plans at non-profit institutions. His areas of expertise include plan design, investment oversight, and fiduciary best practices. 

Before joining PlanPILOT, Brian worked for a decade at Well and Good LLC, a registered investment advisor focused on serving independent private schools. He has also worked at SageView Advisory and TIAA where he was a manager and served in client facing positions for over 25 years. He was part of the original team that established TIAA’s Washington, DC Regional Office. He also served as the Head of TIAA’s Los Angeles Office. 

Brian received his Bachelor of Arts degree in Economics from Bowdoin College. He is an avid traveler and sports fan. He likes to spend time with his wife, Karen and son, Austin. He also enjoys returning to Maine every summer to the family cottage on the ocean.