
Join us for the 35th Annual Small Business & Entrepreneur of the Year Awards! On Thursday, May 28th from 11:45AM-1:30PM at Thorny Lea Golf Club in Brockton.
The Small Business and Entrepreneur Awards are presented to businesses that have displayed employment staying power, growth, innovation, and social responsibility. Please join the Chamber and premier sponsor Eastern Bank in recognizing the achievements and contributions of small businesses and entrepreneurs in creating new jobs and economic opportunities in the Metro South region!
Questions? Contact Hannah McGuire, call (508) 586-0500 x 231 for assistance.
This event is sponsored by Eastern Bank.
About our guest speakers:

Eric Paley is the Secretary of the Executive Office of Economic Development (EOED). He has worked to shape the innovation economy for more than 25 years as both a successful entrepreneur and a leading venture capitalist. As co-founder and Managing Partner of Founder Collective, Paley helped build one of the world’s highest-performing seed-stage venture capital funds, with an investment portfolio that included groundbreaking technology companies across diverse sectors such as transportation, media, healthcare, consumer, advanced manufacturing and enterprise software, including Uber, The Trade Desk, Omada Health, Cruise Automation, Whoop, Formlabs and Airtable. Before Founder Collective, Paley founded and led Brontes Technologies, a hard-tech startup that commercialized novel 3D imaging technology from MIT to enable advanced manufacturing in dentistry. Paley continued to lead the company after its acquisition by 3M in 2006. Paley holds an MBA from Harvard Business School and a bachelor’s degree from Dartmouth College. He lives in Cambridge with his wife and two children.

Clare Bertrand is the Executive Director of Career Strategy and Employer Partnerships at College Board, leading efforts to develop industry and employer partnerships that align education with workforce needs. For over two decades, Clare has worked to bridge education and career, with a focus on leveraging policy, practice, and technology to expand economic mobility for young adults. Clare has an M.S.Ed. in Education Entrepreneurship from University of Pennsylvania.
The Metro South Chamber of Commerce is part of a cohort selected by the U.S. Chamber of Commerce to help address critical workforce challenges by supporting the adoption of new, career-aligned coursework, including AP Business with Personal Finance and AP Cybersecurity. This initiative is designed to better prepare students with practical, in-demand skills and create stronger talent pipelines that meet the evolving needs of employers. Learn more – Addressing the Readiness Gap: Preparing Students for Today’s Workforce. With 84% of employers saying grads aren’t workforce-ready, the U.S. Chamber of Commerce and the College Board are launching new AP courses to equip students with business essential knowledge.

Keegan Shepardson has over 13 years of experience working with small businesses in the areas of sales, marketing, management and business development. Shepardson graduated from New England College in New Hampshire and is father of three young boys. In his previous role as SBA New England Region 1 Advocate, Shepardson focused on outreach, education and building collaborative relationships with federal and state agencies. Shepardson is honored to rejoin The Small Business Administration as the new District Director of Massachusetts.
Prior Award Recipients
| Small Business of the Year | Entrepreneur of the Year | Year |
|---|---|---|
| REV-T RENVisioning Technology | Dr. Ellie Paris Social Bookstore & Ice Cream Cafe | 2025 |
| Medella Dental | BinStar | 2024 |
| Healthier You Wellness Partners | Brockton Beer Company | 2023 |
| New England Tortilla / Mi Niña | Grand Flourish Collective | 2022 |
| Mallory Headsets, Inc. | Fusion Dolls | 2021 |
| South Shore SoftWash, LLC | Empower Nutrition | 2020 |
| Immerse Agency | LAUNCH Web Marketing | 2019 |
| Just Desserts Bakery & Cafe | Shovel Town Brewery | 2018 |
| Wood Palace Kitchens | Epicure Wine & Jazz Bar | 2017 |
| Strange Planet Printing | Elvera’s Cafe | 2016 |
| Maguire’s Bar & Grill | The Sound Lab | 2015 |
| JM Pet Resort | JJ’s Caffe | 2014 |
| Solex Payroll Systems, Inc. | SKy8 Shrimp Farm, LLC | 2013 |
| Vicente’s Tropical Grocery | Sparky’s Import Repair | 2012 |
| McGuiggan’s Pub | Elie Baking Corp. | 2011 |
| Prisoc’s Market | Topnotch Design Studio | 2010 |
| MCG Partners | XPressman Trucking & Courier | 2009 |
| Heights Crossing | UPPAbaby | 2008 |
| Westgate Lanes | Wright Technology Group | 2007 |
| Cindy’s Kitchen | Rob Peters Entertainment | 2006 |
| Northeast Wholesale Nail & Fastener | Spark Street Autobody | 2005 |
| Duplitron, Inc. | The DJ Experience | 2004 |
| Modern Auto Body | The Crazy Chefs Caterers | 2003 |
| United Furniture, Inc. | Top Quality Staffing | 2002 |
| Robert Sharkansky & Company, CPA | Eye of the Tiger Karate | 2001 |
