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Craig Maloney

Chief Commercial Officer​

Craig is Executive Vice President (EVP) and Chief Commercial Officer (CCO) at Benefitfocus. He joined the Benefitfocus team in August 2021. With more than 30 years of experience in the insurance brokerage and benefits administration space, he has a strong passion for health care education, access and empowerment and is committed to disrupting the status quo. Leaning into his servant leadership style, Craig cultivates our growth teams with a holistic approach that focuses on client value and teamwork. ​


Craig is responsible for all facets of our go-to-market strategy, including sales, marketing, communications, sales operations, partnership management and voluntary benefits/insurance catalog. He is a dynamic leader who leads by example and drives a culture of collaboration, accountability and high – yet humble – performance.  ​

Street Cred

Craig received a Bachelor of Science in Finance from Fairfield University in Connecticut. He has an impressive portfolio of executive leadership positions at companies like Marsh and McLennan, Hewitt Associates, Aon, Univers and Maestro Health. Previously, he managed Hewitt’s mid-market benefits administration division, launched Hewitt and Aon’s exchange businesses and led the acquisition of Univers, the industry leader in voluntary benefits, by Aon. It’s safe to say, he’s got the chops (and gray hair)! ​

Hobbies and Interests

Craig is a devoted fan of the New York Yankees and the Los Angeles Chargers. When he’s not at a game or watching them play on TV, he’s keeping active in some way: taking long walks with friends, family or just his headphones, playing golf or hitting the gym. Craig also loves music and, as a former drummer and DJ, he enjoys subjecting his wife and three kids to various musical stylings. Craig is also a major foodie. Having lived in NYC, Atlanta and Chicago, he’s had access to some of the best restaurants in the US, but he’s always looking for recommendations – send them over, if you’ve got any!   ​


Optimism. He truly believes that it isn’t just a frame of mind. It's a true strategic advantage.​