Jonathan Osimo brings nearly 30 years of MTRS experience to his new role
On October 25, 2024, the Board unanimously appointed Jonathan Osimo, a familiar and respected presence at MTRS, as the successor to Executive Director Erika Glaster following her 38-year MTRS career. Jonathan officially began his new role as Executive Director on January 1, 2025. Jonathan’s journey with MTRS began in 1997, and prior to his appointment, had served as Assistant Executive Director of Member Services since 2014.
Beyond his MTRS leadership, Jonathan has been an active voice in the retirement community, serving on the National Pension Education Association (NPEA) Board of Directors since 2020 and currently holding the position of Treasurer. He holds a Bachelor of Science in Business Administration (BSBA) degree from Nichols College.
Now that Jonathan has wrapped up his first “retirement season” as Executive Director, met one-on-one with every MTRS employee, and is preparing for his first system upgrade, MTRS News caught up with him to reflect on his career, share his vision for the future—and talk about his unexpected hobby: skydiving.
Let’s get to know a little more about Jon O
Can you tell us a little about your history with the MTRS?
I joined the MTRS in 1997 as a Retirement Counselor, focusing on benefit calculations, benefit counseling, and educational seminars. In 2000, I became Western Regional Director, and in 2004, I was appointed Director of Member Services. Before being named Executive Director in 2025, I served for ten years as Deputy Executive Director and Chief Benefits Officer, managing four agency departments within the Member and Employer Services Division. This division is responsible for benefits administration, service credit purchases, member education, and deduction reporting.
What excites you most about leading the Massachusetts Teachers’ Retirement System?
I’m excited to lead our team of dedicated professionals who share a strong belief in our mission: to ensure that members of the Massachusetts Teachers’ Retirement System achieve and maintain a successful and secure retirement through responsible benefits administration, financial integrity, and the provision of outstanding services.
What are your top priorities in your first year as Executive Director?
In my first year, I will work with our team to implement any needed organizational changes and to ensure the successful completion of our computer software upgrade project.
What’s something about you that people might be surprised to learn?
A few years ago, I went skydiving for the first time with my entire immediate family in Pepperell, MA – and we all loved it!
What message would you like to share with our educators and retirees as you begin your tenure as Executive Director?
First, I want to express my deep appreciation for the impact our educators have on public education in Massachusetts. To our active educators, I want you to know that we are committed to ensuring a smooth transition to your retirement. To our retirees, I want you to know that we will continue to support and assist you in every way possible throughout your retirement.