Bob Flynn

Director of Workforce Iniatives

Bob joined Dalio Education in 2025 as the Director of Workforce Initiatives.  He workscollaboratively with grantee partner organizations to co-design and implement workforce programs offering comprehensive services that enable disconnected young people to secure meaningful employment and pursue long-term economic mobility.

Bob has over 20 years of experience designing and leading equity-centered educational and youth development initiatives. He brings a deep commitment to supporting young people who are underserved, off-track, or disconnected from traditional systems. 

As Director of a re-entry program at the Suffolk County House of Correction, he partnered with four local non-profit agencies to deliver holistic academic, workforce development, and case management services to incarcerated men and women returning to the community. 

He later served as Dean of Academic Support & College Pathway Programs at Bunker Hill Community College, where he led college access and academic support programming for students.  In that role, he developed the college’s Dual Enrollment Program, which helped low-income and first-generation high school students complete college-level courses while in high school.

Most recently, Bob served as Associate Vice President of National Programs at Sandy Hook Promise, where he oversaw the design of K-12 violence prevention programming for schools across the country.

Bob holds both a B.A. in English Education and an Ed.M. in Reading Education from Boston University.