Worcester Business Journal

wbjournal.com | August 24, 2026 | Worcester Business Journal 21 Kate Gallo Megraw, 36 Chief operating officer & chief information officer, Webster Five, in Auburn Residence: Southampton Colleges: Assumption University; Southern New Hampshire University Kate Gallo Megraw has built a career around modernizing community banking, including helping launch one of Massachusetts' few new banks. At Webster Five, Megraw has retooled the bank's technology stack, from infrastructure to customer-facing applications, while introducing continuous-improvement models across technology and operations. She led Webster Five through a full core conversion, one of banking's most complex technology projects. About a year ago, she added chief operating officer to her chief information officer responsibilities, taking a larger role in the bank's day-to-day operations and long-term strategy. Earlier in her career, Megraw helped launch a de novo bank in Springfield, raising $25 million from local shareholders, securing regulatory approvals, and establishing the brand with a small team. Megraw serves on the board of Open Sky Community Services, where she is a member of its finance and programs committees. She visits programs across Central Massachusetts to interact directly with employees and clients. What TV show, book, or movie best describes your life journey so far? It hasn't been written yet. What is the best restaurant in Central Mass.? deadhorse hill What one thing should older generations understand most about young professionals? There's often more than one journey to the same end. What one person would you most like to meet in the next 40 years? The future versions of my daughters 4 0 U N D E R F O R T Y Jonah Glickman, 29 Vice president, NAI Glickman Kovago & Jacobs, in Worcester Residence: Grafton College: UMass Amherst Jonah Glickman left banking to start from scratch in commercial real estate brokerage. Three years later, he has surpassed $53 million in transaction volume. Glickman has closed 45 transactions encompassing more than 560,000 square feet. His largest came in 2026, when he closed the $13.5-million sale of a 134,648-square-foot industrial building in Marlborough. His five years underwriting commercial real estate loans inform his approach to brokerage, giving him experience analyzing financial statements, cash flows, and risk. Before changing careers, Glickman helped small businesses navigate the federal Paycheck Protection Program loan forgiveness process during the coronavirus pandemic. Glickman serves on the Worcester Young Businessmen's Association board and the committee for the Lori Lajoie Charity Golf Tournament benefiting Seven Hills Foundation. He has spent the past decade as a secondary caregiver for his mother, who has early-onset Alzheimer's disease. What TV show, book, or movie best describes your life journey so far? "Ted Lasso" – Earning credibility and trust from scratch, the hard way, rather than assuming it. Why do you choose to live in Central Mass.? The people. Having lived here my entire life, the people are what make our communities, businesses, and places great. Who helped you the most in your professional journey? My father, Jim. He built his own name in this industry over decades and gave me room to build mine, not just inherit his. CONGRATULATIONS This recognition reflects your dedication, inspiring leadership, and commitment to excellence. Your path is defined by ambition and success, and this honour is truly well earned. Keep breaking new ground and leading with purpose —you're destined for even greater achievements! ASHLEY BARRY "SUCCESS IS NOT A MATTER OF LUCK. IT IS HARD WORK, DETERMINATION, STUDY, LEARNING AND THE ABILITY TO GET BACK UP AFTER FALLING." – LARRY ELDER With appreciation, The Cunningham Equities Team Building Communities. Preserving History. Inspiring the Future. CONGRATULATIONS, JAMES! Your passion for revitalizing historic properties, investing in our communities, and leading with integrity has made a lasting impact throughout Central Massachusetts. We are proud to celebrate your recognition as one of the Worcester Business Journal's 2026 40 Under Forty honorees and look forward to all that lies ahead. W W

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