Chris Massad

Chris Massad, CRPS™, currently serves as the Head of Retirement Sales Strategy at Gusto since November 2025. Prior to this role, Chris was the Head of Sales Strategy at Guideline from December 2019 to November 2025, where responsibilities included leading go-to-market strategies and sales initiatives that enhanced revenue performance across a large sales organization. Chris also held various sales roles at Guideline, including Sales Solution Architect, achieving an 83 percent win rate on 172 opportunities and driving significant product launches, and Senior Account Executive, setting records with 2,327 plans sold and influencing $1.32 billion in assets under management. Earlier career experiences span management positions in the hospitality sector and roles within the criminal justice system. Chris holds a Master of Arts in Public Management from The Johns Hopkins University and a Bachelor of Science in Criminal Justice from Northeastern University.