Stephen Grossman, CLU, LUTCF, has more than 35 years of experience in the insurance and financial services industry. He serves as General Agent of MassMutual Metro New York, a general agency of Massachusetts Mutual Life Insurance Company, serving individuals and businesses throughout the New York metropolitan area. Under Stephen’s leadership, MassMutual Metro New York has grown to include approximately 100 full-time financial professionals, more than 1,000 brokers, and a staff of 15. As of December 31, 2025, the agency manages and services more than 25,000* policyholders and over $1.8** billion in assets serviced.

Stephen holds licenses in Life & Health and Property & Casualty insurance, along with FINRA Series 6, 7, 24, 26, 63, and 65 registrations. Stephen began his career in financial services in 1991 with Prudential Financial as a Financial Services Representative in Queens, New York. During his tenure, he qualified for conference recognition annually, consistently reported more than 100 lives each year, and earned Disability Rookie of the Year honors.

In 1995, he was promoted to Sales Manager in Queens, where he built a successful scratch unit and qualified for the President’s Citation as a Top 10 Sales Manager. He was later appointed to lead a struggling district office in Westchester County, transforming it into the company’s #1 office and earning the prestigious President’s Trophy. In 1997, Stephen was promoted to Managing Director in Lawrenceville, New Jersey. In 2001, he joined Penn Mutual as General Agent in New York City, achieving numerous honors, including Chairman’s Trophy recognition and leading the firm’s #1 agency.

Stephen joined MassMutual Metro New York in 2008 as General Agent in New York, where he successfully developed a scratch agency into a GAMA Master Agency. His accomplishments include:

• 9 Chairman’s Bowl Awards(1)

Gold: 2010, 2011, 2016, 2021

Silver: 2009, 2020, 2022

Bronze: 2012, 2013

• 5 Crystal Achievement Awards (2)

2011, 2012, 2013, 2016, 2021

• Burvin E. Pugh Agency Building Award (3)

• FINSECA Master Agency Awards (4)

2022, 2023, 2024

• Agency Best Year Ever Awards

2003, 2013, 2016, 2020, 2021

• Net Field Force Awards (5)

2012–2018 Stephen holds the Chartered Life Underwriter (CLU) and Life Underwriter Training Council Fellow

(LUTCF) designations.

Personal Background

Outside of his professional career, Stephen is passionate about competitive marathon running and Ironman competitions, consistently finishing among the top athletes in his age group. He has completed the Boston Marathon and nine full Ironman races, achieving a personal-best marathon time of 2:58 and a 10:30 Ironman finish. Born and raised in Brooklyn, Stephen currently resides in New York City with his wife, Marnie, their children, Maya and Noah, and their dog, Bonnie.