About Winston
Hello, my name is Winston Daley and I am running for a seat on the Milton Select Board. My wife Nicole and daughter Zahria and I have lived in Milton for 11 years. In that time I have been a dedicated community leader, parent, and advocate for positive change. I have a passion for collaboration and a vision of building a stronger future for all of Milton. I am excited to bring new ideas and proactive leadership to the Select Board.
I was born in St. Ann, Jamaica and moved to Boston, MA at the age of 10. I am a proud BPS graduate having attended Boston Latin School and South Boston High. I graduated from Suffolk University with a BSBA in Business Management and Entrepreneurial Studies and received my masters in Sports Leadership from Northeastern University. At Suffolk I played basketball all 4 years, was a 2 year captain and was inducted into the Suffolk Hall of Fame in 2024. In sports I was a member of some very successful teams and this taught me that great achievement requires teamwork.
I spent the first 13 years of my career working in financial services and institutional investing, at State Street Bank, BNY Mellon and Brown Brothers Harriman and Co. In 2015 I felt a pull to give more to my community and made a career switch to working with youth and non-profits full-time. For the last 10 years I have worked in building, supporting and running youth programs in and around Milton. In 2020 I entered the world of tech and startups as I founded a company to help diversify the teaching profession and connect teachers to schools. I now remain in the startup space as an investor and member of one of the best known angel investing groups in the Northeast.
My involvement with Milton began at Tucker Elementary when my daughter Zahria was in kindergarten. I was a member of the Tucker Site Council and started the Tucker Basketball League. I have been a board member of the Milton Foundation for Education helping to fund and support our schools. As a dad and a community member, I believe we all fare better when our youth - and the educators who guide them - have the resources they need to succeed.
I am a Town Meeting member in Precinct 2 and was elected as a Parks and Recreation Commissioner in 2022. You may have also seen me coaching basketball and softball around town. Initially through sports and then through music lessons, early morning math programs, book drives, and field days, I have aimed to create opportunities for Milton’s youth while supporting our educators and collaborating with other parents.
I believe my professional path and experiences in Milton have prepared me for joining the Select Board at this pivotal time for our town. My career in finance required long-term planning and accounting. My non-profit work requires an understanding of youth, family and community needs. My time as a startup founder required hustle, vision, creativity, and vigilance. Now as an investor, I measure risk and assess the probability of success.
As the father of a soon-to-be Milton High graduate and the first person in my family to own a home, I understand the importance and benefit of investing in our town’s future. Every decision and indecision made today impacts the quality of life for future generations. We need positive, collaborative, forward thinking leadership. I want to be a part of improving our education, local services, and economic opportunities.