CEOs You Should Know - Boston

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.

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Kevin started his journey into entrepreneurship at the age of 18 with the opening of his first restaurant, growing that small business into 6 restaurants and banquet facilities in 3 years, all by the age of 21.

Kevin was first introduced to the dry cleaning industry after he purchased an established restaurant from the founder of Lapels Dry Cleaning in 2001. Drawn to the low cost of industry goods and by the lack of perishable inventory, Kevin quickly became an active partner at Lapels. After several years of learning the dry cleaning business, he bought out his partner, and then, as CEO, began growing Lapels from 20 storefronts to over 100 storefronts in 2021.

Earlier this year, Kevin acquired the Martinizing, 1-800-Dry-Cleaning, Pressed 4 Time, Dry Cleaning Station, and Bizziebox franchises and created a newly formed entity, Clean Franchise Brands. Clean Franchise Brands affords unique value to its franchise partners around the globe by offering operations strategies and marketing systems that continue to propel these brands to further growth.

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A 39-year community banker who started his career as a teller, Bob is CEO and Chair of the Board of Eastern Bankshares, Inc. and Eastern Bank. He is also Chair of The Dimock Center and a former Chair of the Massachusetts Business Roundtable.

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Jack Clancy was appointed as the CEO of Enterprise Bank since 2007. He joined Enterprise Bank as the Chief Financial Officer and Treasurer during its founding in 1988. Enterprise Bank is headquartered in Lowell, MA with 26 offices throughout the Merrimack Valley, Essex, and North Central regions of Massachusetts, and across Southern New Hampshire.

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Ernie Boch, Jr. is a renowned business leader, entrepreneur, and philanthropist in Massachusetts. Mr. Boch currently serves as President and CEO of Ferrari of New England, an official Ferrari dealer, and Subaru of New England, the multibillion-dollar company that distributes Subaru vehicles and parts throughout the six New England states.

Boch’s charitable foundation, Music Drives Us, is a 501(c)(3), non-profit organization that funds musical opportunities for the underserved throughout New England. Boch’s lifelong love of music, combined with his passionate dedication to Music Drives Us, ensures that music will be taught in schools across New England for generations to come.

Stay connected with Ernie on social media – @ErnieBochJr

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Joe is CEO and President at Needham Bank, leading its growth as a top “Super Community Bank.” He also has a long history of community involvement as former Chairman of Tufts Medical Center, Trustee and Treasurer for the Boys & Girls Club of Boston, Executive Committee member at Mass Business Round Table, Independent Director at First Help Financial, and a Director of the 100 Club of Mass. He frequently serves as a guest lecturer at a number of college and industry events.

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Christopher Oddleifson is the Chief Executive Officer of Rockland Trust Company and the President and Chief Executive Officer of its parent, Independent Bank Corp. (Nasdaq Global Select Market: INDB). Rockland Trust is a full service commercial and retail bank with over 1,400 employees and serves more than 340,000 customers.

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The Neighborhood Assistance Corporation of America (NACA) is a non-profit organization dedicated to economic justice through home ownership and community activism. NACA is the largest HUD certified counseling agency with more than two million members nationwide.

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Aron Ain serves as Chief Executive Officer and Chairman of UKG (Ultimate Kronos Group). Ultimate and Kronos merged in April 2020 to create UKG, one of the world’s most innovative human capital management and workforce management companies. Aron joined Kronos in 1979 and played a role in nearly every functional department at the company until becoming CEO in 2005.

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Get to know Darryl J. Fess, President & CEO of Brookline Bank. Since 1871, Brookline Bank has built a legacy of consistent financial strength, trust, outstanding banking services, and strong customer relationships. Today, they deliver an expanding array of valuable banking and financial services geared to helping individuals and businesses manage their finances.

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