Welcome to Lead & Legacy, an inspiring evening bringing together LeadBoston alumni, emerging leaders, and people who are ready to invest in their own leadership journey. Tonight, enjoy meaningful conversations, expand your network, hear from leaders who have been where you are, and discover the community behind one of Boston’s most impactful leadership programs.
Agenda:
6:30 PM: Arrival & Connection Hour
7:15 PM: Welcome Remarks
7:20 PM: Alumni Micro-Panel
8:00 PM: Social Hour
8:30 PM: Event Concludes
Panelists:
Pedro Cruz, Executive Director, Office of Youth Engagement and Advancement, City of Boston
Pedro Cruz is the inaugural Executive Director of the City of Boston’s Office of Youth Engagement & Advancement (OYEA), launched under the Wu Administration in 2023. Over the past few years, Pedro has led the office in building its foundation and shaping a citywide vision for youth leadership, equity, and opportunity. Under his leadership, OYEA has built a network of 1,700 youth-serving professionals across 500+ youth-serving organizations to help break down the silos and to better serve the young residents of Boston. His office launched Boston After Dark to provide safe and vibrant evening programming, and deepened investments in civic engagement through initiatives like the Mayor’s Youth Council and the Mayor’s Youth Summit. His work has positioned OYEA as a central hub for elevating youth voices and ensuring young people are at the forefront of decision-making in Boston.
A lifelong Bostonian, first-generation Puerto Rican, and proud Boston Public Schools graduate, Pedro brings his lived experience and organizing background to every aspect of his work. Before stepping into city government, he directed IBA’s Youth Development Program in Villa Victoria, where he created innovative programming, mentorship opportunities, and learning pods during the pandemic that ensured youth remained connected and supported. His ability to combine creative arts, civic engagement, and community-building continues to guide his approach in building sustainable systems of support for Boston’s young people.
Dalinda Ifill-Pressat, Assistant Vice President of Marketing & Communications, Children’s Services of Roxbury
Dalinda Ifill-Pressat serves as Assistant Vice President of Marketing & Communications at Children’s Services of Roxbury (CSR), where she leads strategic, results-driven marketing and brand initiatives that advance the organization’s mission and expand its impact across Massachusetts. With more than 20 years of combined professional and academic experience in communications, journalism, and marketing strategy, Dalinda is known for aligning brand voice with measurable outcomes and strengthening organizational credibility through purposeful, community-centered storytelling.
Since joining CSR in 2019, she has played a key role in elevating the organization’s visibility and cohesion, progressing from Director to Assistant Vice President in 2025. She oversees integrated communications strategies that support CSR’s culturally responsive programs and has helped position the organization as a trusted nonprofit leader in child and family services.
Dalinda leads with a collaborative, relationship-centered approach, building strong internal and external partnerships that drive sustainable impact. She holds a B.S. in Communication Studies from Northeastern University and a M.A. in Journalism from Emerson College and began her career in television production at CBS Boston/WBZ-TV.
A native of Barbados, Dalinda is guided by a deep belief in the transformative power of equitable access to education and information. She is a 2023 Lead Boston alumna and enjoys curating meaningful experiences, event planning, and spending time with her husband, daughter, family, and close friends.
Michael Reid, VP – Branch Manager, Eastern Bank
Mike Reid is Vice President at Eastern Bank managing a branch in the South Shore area. Mike has been in banking for 13 years and retail management for 19 years. He joined Eastern Bank in December 2018 and had previously matured as a Branch Manager at TD bank and getting his start as a banker at Bank of America 2013.
Mike is passionate about being in the service of others and his civic engagements as he currently serves as a board member for Company One Theatre. A 501c3 organization that builds community at the intersection of art and social change. The vision is a Boston defined by justice, equity, and artistic innovation. Michael remains focused on the treatment of all people and how to create social change.
Mike is a Deacon and in leadership for Hope Lighthouse Christian Church in Somerville, MA. He most enjoys doing sermons and sharing his life’s reflections & testimonies of God’s favor and grace throughout his life. He stays very close with his two sons Anthony (21) and Nabi (16) and loves connecting with friends and family. Mike also considers strangers his potential friends.
