CEOs You Should Know Boston

CEOs You Should Know Boston

CEOs You Should Know is iHeartMedia Boston's showcase of businesses that drive New England's regional economy. Hear from key business leaders who contribute to the vibrant and growing community.

Episodes

May 12, 2025 1 min
Bill joined Plymouth Rock in 2016 and is in charge of our property insurance business and reinsurance programs. Bill has over 30 years of experience in the insurance industry. Bill was formerly President of Bankers Insurance, winning a Celent Model Insurer award in 2014 for simplifying homeowners insurance shopping. He also founded a startup with a new approach to flood insurance and has held senior positions at Farmers Insurance, ...
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Over the span of his 20+ year career in financial services, Ryan Bailey has focused on enhancing customer experiences and supporting communities at every turn.

Prior to becoming President and CEO of CSB, Ryan held leadership positions at some of the country’s most respected financial institutions, including TD Bank, Bank of the West, JP Morgan Chase, Fifth Third Bank, and Bank of America. His most recent role was as the Head of Reta...
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Michael Christian has served as Board President of Someone Else’s Child, Inc. (SEC) for nearly 25 years. The foundation supports youth causes throughout the U.S., Africa, and Central America with areas of emphasis including education, the arts, youth living with disabilities, economic justice, and collective action efforts. SEC addresses disparities by investing in opportunities for young people to live, learn, grow and engage as c...
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Phillip Eng is the General Manager and CEO of the Massachusetts Bay Transportation Authority (MBTA). A Civil Engineer with nearly 40 years of transportation experience, including President of the Metropolitan Transportation Authority’s (MTA) Long Island Rail Road and Interim President of New York City Transit, Mr. Eng brings his abilities to spearhead challenging initiatives, modernize aging systems and prioritize safety to bear fo...
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Attorney Sean Flaherty, Managing Partner at Keches Law Group, is a former member of the Local 7 Steel and Ironworkers Union. He represents injured workers in all phases of workers’ compensation litigation including Conciliations, Conferences and Hearings before Administrative Law Judges at the Department of Industrial Accidents as well as Social Security Disability claims, employment discrimination, sexual harassment, and wrongful ...
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October 7, 2024 58 secs
Terry Andre has led AmCoat as its CEO since 2010. With more than twenty years of contract manufacturing experience, he is uniquely qualified to help dealers develop their businesses and keep the supply chain moving. Terry and his wife Kathy, reside in Destin, Florida and have three adult children.
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Jenny Holaday brings her extensive background in the casino industry to her role of President of Encore Boston Harbor, which she assumed in August 2021. Previously the executive vice president of operations, Jenny oversees all aspects of the $2.6B resort’s operations and leads a team of nearly 3,000 employees.

Jenny has lived and worked in gaming regions from the East Coast to Nevada and many places in between. She has held executiv...
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With one foot firmly in Reno and the other across the pond at our Bristol, UK office, Jarrod’s globetrotting nature has led him to make meaningful connections with people all over the world. His attention to listening first let’s him learn what makes people tick and, admittedly, helps him harness the insights to propel Noble’s success.

Over the last two decades Jarrod has grown our creative digital performance marketing agency from ...
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August 26, 2024 1 min
Paul is the founder of Boston Venture Studio. Paul has previously co-founded and successfully sold six startups – Kayak, Lola, Moonbeam, GetHuman, Boston Light and Intermute.

Paul is also the founder of four nonprofits – Summits Education in Haiti, Embrace Boston, The Winter Walk for Homelessness, and the Bipolar Social Club.

Paul is the subject of Tracy Kidder’s book “A Truck Full of Money”. You can hear an interview with Paul on “H...
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Kate Fox is the executive director at the Massachusetts Office of Travel & Tourism in the Healey-Driscoll Administration. A seasoned tourism professional with 25 years of experience, Kate was previously the executive director of Destination Salem, the city’s Office of Tourism & Cultural Affairs, where she oversaw year-round destination marketing efforts for nearly two decades.  Fox spent five years as the Director of Cultur...
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July 29, 2024 1 min
Ben Garthwaite serves as chief executive officer of Fors Marsh and guides the company’s business growth and diversification. Ben cultivates a purpose-driven culture focused on using business as a force for good, with the belief that businesses must share responsibility for strengthening the systems in which we operate. He is committed to evolving company policies and practices so that each of Fors Marsh’s key stakeholder groups—com...
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Dr. Stephen Spinelli Jr. is the 14th president of Babson College, having assumed the role in July 2019. A lifelong entrepreneur, President Spinelli has spent his career at the intersection of academia, business, and philanthropy. Under his leadership, Babson College was named the 10th best college in the United States by The Wall Street Journal and has retained its long-standing place atop U.S. News & World Report’s undergradua...
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Chef Matt is a New England native with almost 30 years of culinary experience, working through the ranks at many local Boston establishments. Through his career, Matt has opened up a remarkable 16 restaurants – across the United States and even abroad in Ireland. He’s now at the helm as President & COO of one of New England’s most iconic restaurants – Legal Sea Foods. Legal has 26 restaurants, and soon to be 27, with an expansi...
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Lisa is responsible for safe, reliable and affordable energy delivery to National Grid’s customers in New England, overseeing gas and electric operations in Massachusetts and transmission in New England. She is committed to enabling the Commonwealth’s energy transition and ambitious climate goals, while keeping Massachusetts competitive.

Prior to joining National Grid, Lisa served as the Chief Executive Officer of the Massachusetts ...
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A tireless advocate for the hungry for more than 40 years, Catherine D’Amato assumed the leadership of GBFB in 1995. During her tenure, she has transformed GBFB into a $180 million charitable business and increased GBFB’s distribution from 7.5 million meals a year to nearly 90 million healthy meals per year. She has grown GBFB’s network to include 600 partner food pantries, meal programs and direct distribution sites across the 190...
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Todd Krinsky was appointed President and CEO of Reebok in September 2022 after three decades of unwavering service to the company. As a Reebok “lifer”, Todd leads the company’s continued commitment to creating industry-leading, innovative products and embodying its “irreverent” brand identity.

During his 30 years at Reebok, Todd has touched every aspect of the business - from category leadership to merchandising management to sports...
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An educational technology, digital health, and social impact entrepreneur, Michael London has created more than one billion dollars in company value throughout his career. Michael’s belief that "student mental health is the defining higher education issue of our time" led him to create Uwill. Founded in 2020 to assist campus counseling centers as they faced overwhelming student demand for mental health support, Uwill has quickly ea...
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Leonard Spada is the founder of Spada Law Group LLC. Upon graduating from Boston College Law School in 1991, Len accepted a prestigious one-year appointment as a Judicial Law Clerk for the justices of the Massachusetts Superior Court. It was during this time that Len worked closely with the Judges of the Superior Court assisting them in deciding matters that came before the court in both civil and criminal trials. The clerkship was...
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Denise Woodard is the Founder and CEO of Partake Foods, the allergy-friendly company that was inspired by her daughter’s experience with food allergies. Key moments this year include that Partake Foods announced it became a Certified B Corporation, and launched a collab with Ben & Jerry’s! Created in 2016, Denise started the business by self-distributing (selling cookies out of her car around NYC) and self-funding (depleting he...
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Stephen has devoted his career to supporting the educational promise of all, from the youngest children to high school students and adult learners -- working to realize his vision and belief that everyone at every age deserves a great education. Stephen was named CEO of Bright Horizons in January 2018, and over the last decade, he has held leadership positions throughout the organization including President, Chief Development Offic...
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