MEET OUR TEAM
John S. Rocco, CLU®, ChFC®
Principal | Rocco Insurance and Financial Group
Continuing a Legacy of Integrity and Guidance
As the successor and cousin to the late John J. Rocco, CLU®, MSFS, founder of Rocco Insurance and Financial Group, John S. Rocco carries forward a proud family legacy built on trust, service, and enduring relationships. Having joined the firm as a partner in 2012, John continues the mission his cousin began more than six decades ago—helping families and business owners achieve financial confidence through thoughtful planning and personal care.
A Purpose-Driven Career
John brings a deep commitment to guiding clients through every stage of their financial journey. With a background in business management from Fairfield University and advanced professional designations as a Chartered Life Underwriter (CLU®) and Chartered Financial Consultant (ChFC®) from The American College, he combines technical expertise with a hands-on, relationship-based approach.
Specializing in comprehensive financial strategies, John helps clients address their protection, college funding, retirement, and estate planning needs—ensuring their goals align with long-term security and legacy preservation.
Leadership and Professional Excellence
Recognized as a New York Life Chairman’s Council Advisor, John ranks among the company’s top financial professionals nationwide. His success reflects a career built on dedication, ethical leadership, and an unwavering commitment to his clients’ best interests. Under his guidance, the firm continues to thrive while remaining true to the values established by its founder—integrity, compassion, and lasting relationships.
Together with John L. Howard Jr., CLTC, RICP, and Christina O’Connell, FSCP®, John leads the firm with a shared dedication to the principles that have guided it since its founding—integrity, service, and the pursuit of excellence.
Beyond the Office
John resides in Natick, Massachusetts, with his wife Kimberly and their children, Owen and Olivia. When he’s not at work, John loves spending time with his family and cherishing the moments that remind him why helping others secure their futures matters so deeply.
CA Insurance Lic. #0K10982
John L. Howard, Jr., CLTC
Partner
John L. Howard, Jr. is a strategic innovator, natural problem solver, and a long-time entrepreneur. For him, his work is all about helping people and their families. John guides his clients with holistic planning practices that help business owners and professionals protect their income and preserve their wealth.
An agent of New York Life, John’s a registered representative of NYLIFE Securities, and an investment advisor representative with Eagle Strategies. His specialties include continuity strategies, estate planning, college funding, risk management, long-term health care and retirement planning for business owners, executives and their families. He enjoys solving problems faced by family-owned businesses and the transfer of ownership from one generation to the next.
John has a Certification in Long Term Care (CLTC) and is enrolled in the CFP program at the American College. He is a proud member of NAIFA and a qualifying member of the Million Dollar Round Table* since 2007. When not serving clients, he spends time with his family in Concord, Massachusetts, hiking, playing golf and cooking.
CA Insurance Lic. #OF77866
Christina O’Connell
Registered Representative & Agent
Christina O’Connell is a registered representative and agent at Rocco Insurance and Financial Group. She has been with Rocco Insurance and Financial Group since 2019 and transitioned into the agent role in 2023. Christina works with families and individuals to create a plan to help achieve and protect their financial goals. Christina is detailed oriented and passionate about relationship building and delivering superb client service. Outside of the office, Christina enjoys spending time with her family and cheering on her two active girls.