Our Team

Matthew Rubin

Managing Partner

Originally from New York City, Matt graduated from Tulane University’s A.B. Freeman School of Business. He began his professional career as a Teach For America Corps Member in New Orleans, where he taught Kindergarten and was recognized as the school’s 2013 Teacher of the Year. Matt joined New York Life in 2013 as a Financial Professional, earning Executive Council* recognition while focusing on wealth accumulation and insurance for young professionals, teachers, and business owners. Drawn to leadership, he transitioned to management and was promoted to Partner and later Senior Partner in the New Orleans General Office, where his teams earned numerous national honors, including West Central Zone Partner of the Year and National Top 50 Partner recognition.

In 2018, Matt became Corporate Vice President for New York Life’s West Central Zone, overseeing coaching and development for 130 managers across 29 offices; the zone earned the Agency’s Zone Award of Excellence in 2020. In 2021, Matt was appointed Managing Partner of the Richmond General Office. Under his leadership, the Richmond Office achieved remarkable results in both agent production and retention as well as the promotion of 4 new managers.

Matt currently serves as Managing Partner of the Greater Chicago General Office, where he continues to focus on leadership development and growth in one of New York Life's flagship offices. Matt holds Life and Health licenses and FINRA Series 6, 7, 24, 63, and 66 registrations. He is supported by his wife, Brynna, son Jack, and two dogs, Moses and Nyx. 

^{*Awarded by New York Life Insurance Company for outstanding sales achievements. Council is an annual company recognition program based on agent production from July 1- June 30.}

Justine Annoreno

Partner

Justine Annoreno is a Partner in the Greater Chicago General Office. Justine joined New York Life in 2019. She found early success as an agent, qualifying for New York Life's Executive Council. In 2024, Justine joined the leadership team. She focuses on recruiting and development of new agents in the Greater Chicago General Office.

Kirk R. Johnson

Executive Director of Development

A native of the Chicagoland area, Kirk spent 6 years in Colombia, South America where he became fluent in Spanish. He attended North Park University prior to beginning a career in Health Insurance Operations while also obtaining his MBA. Kirk entered the financial services industry with New York Life Illinois General Office in 2001, qualifying for Council 5 times including President's Council, before entering management in 2008. After becoming a Development Manager in 2010, Kirk gained experience in 3 diverse offices and was promoted to Director of Development in 2017. In 2020 Kirk was promoted to Regional Director of Development responsible for the Development Teams for all of Chicago. He was promoted to Corporate Vice President in 2023. Kirk has consistently been a leader in agent and partner development and retention. Kirk and his wife reside in Libertyville and have 4 boys.

Jason P. Spears

Director of Development

Jason P. Spears joined New York Life Insurance Company in 2012 as an agent in the Montgomery General Office. After achieving various recognition and awards he was called into management. This led him on a journey of serving in various General Offices in the Development Manager role throughout the West Central Zone, (Nebraska, Greater Chicago, Oklahoma City, Illinois GO, Chicago-North Shore, Wisconsin, Dallas, & Houston) he now serves in the New York Life Greater Chicago Office; a Tier I General Office in the New York Life Agency System. Some of his responsibilities include but are not limited to the following: retention, marketing, increasing sales, case development, and new agent development.

Inspired by his father, mother, and several other family members who have served as teachers, principals, and school administrators, Jason’s move to training and management work naturally fits the family’s commitment to facilitating others’ learning experiences.

Jason is a graduate of Tuskegee University with a B.S. in Finance and Auburn University with a M.S. in Urban Planning & Community Development. While working with New York Life he has obtained numerous securities licenses. He dedicates himself to helping individuals obtain financial stability.

In his downtime, Jason moonlights as an unpaid TV and movie critic and chef. He is an avid sports fan who enjoys exciting games, but his allegiance belongs to teams from his alma mater, Tuskegee University. He also loves to spend time with his family in the southeast.

Jennanne Dougherty

Director of Agency Standards

As the Director of Agency Standards, I bring more than a decade of experience and leadership to New York Life, where I have proudly served since 2009. In my role, I am committed to upholding the highest levels of professionalism, ethics, and operational excellence across our agency network.

Before joining New York Life, I spent four years in the financial services industry, including serving as an Investment Advisor with Morgan Stanley Smith Barney. This early experience provided a strong foundation in client service, regulatory awareness, and financial strategy—skills that continue to inform my work today.

I hold a Juris Doctorate, which has strengthened my ability to navigate complex regulatory environments and support the company’s commitment to integrity and compliance.

Outside of work, I am deeply devoted to my family. My husband and I are the proud parents of three wonderful children who keep life full, joyful, and always interesting.

Abby Rexhepi

Service Leader

Abby Rexhepi,  Service Leader,  in the Greater Chicago General Office. With over 30 years of experience in banking and financial services, she brings deep expertise in commercial lending, business banking, management, and audits, with a strong focus on compliance and operational excellence.

 Passionate about helping clients succeed, Abby is equally committed to mentoring professionals and building high-performing teams. A Chicago native, she is fluent in Albanian, proud of her three adult children, and an avid NFL enthusiast.