In 2024, Masiello took the role of chair at the New England-based brokerage his father founded in 1966. The Masiello Group is a second-generation family company with close to 600 agents who do approximately $1.6 billion in annual sales. In 2024, the firm launched a website to share listing compensation percentages. The Masiello Group also includes title, referral and other real estate services.