Four US insurance organizations have announced senior appointments this week spanning personal lines operations, specialty board governance, insurtech strategy and employee benefits advisory services.
Plymouth Rock Assurance has promoted Michelle Trindade (pictured, left) to chief operating officer of the Plymouth Rock Management Company of New Jersey, where she will oversee strategic vision and operational execution for the company's Direct Group. The company simultaneously promoted Nilu Tabrizi (pictured, right) to vice president, Customer Service, bringing together the Customer Service, Sales Center and Underwriting Operations functions under unified leadership.
Trindade joined Plymouth Rock in 2025 and most recently served as vice president of Marketing and Customer Service for the Direct Group. She brings nearly 30 years of industry experience spanning operations, customer experience, claims, underwriting, sales, marketing and technology transformation. Prior to Plymouth Rock, she held executive leadership roles at GEICO, where she led large-scale operating organizations and multi-billion-dollar business units.
Tabrizi brings more than 20 years of insurance leadership experience and has been with Plymouth Rock since 2019. In her most recent role she helped drive record performance in quote rates, close rates and sales productivity across the Direct Sales Center.
"Michelle has made a significant impact in a short period of time. She has earned the trust and confidence of our leadership team through her strategic vision, operational expertise, and ability to drive meaningful results," said Greg Kalinsky, president and CEO of Plymouth Rock Management Company of New Jersey.
AM Specialty Insurance Group has appointed Michael Watson to its board of directors. Watson is the founder and former chairman and CEO of Canopius Group, the global specialty reinsurance business he built from a small Lloyd's syndicate into one writing more than $4 billion in gross written premium - leading it through two management buyouts, two sales to strategic investors and four major acquisitions over more than two decades.
Watson brings more than 45 years of financial services experience across London, New York, Bermuda and Ireland. He is a former member of the Council of Lloyd's and a former board member of the Lloyd's Market Association, and began his career at Arthur Andersen, where he qualified as a Chartered Accountant.
"Michael's appointment to our board represents a significant addition to the group. His experience in building and scaling a global specialty insurance business, combined with his deep Lloyd's market experience and strategic perspective, will be highly valuable as we continue to develop AM Specialty's platform and growth," said Shevawn Barder, group CEO of AM Specialty Insurance Group.
Goosehead Insurance has appointed Eben Hewitt as chief technology officer. Hewitt joins from Hyatt Corporation, where he served as global chief information officer overseeing engineering, data and AI, infrastructure, cybersecurity, technology operations and enterprise applications. He has previously held senior technology leadership roles at Sabre Hospitality Solutions, Choice Hotels and O'Reilly Media.
At Goosehead, Hewitt will lead the company's technology strategy including expansion of AI-powered capabilities, data and analytics platforms and the continued development of Digital Agent 2.0.
"Goosehead has built an industry-leading platform and a culture of innovation. I look forward to helping advance the company's AI and technology strategy to empower agents, enhance client experiences, and support accelerated growth," said Hewitt.
Alliant Insurance Services has hired Kristin Searcy as senior vice president within its Employee Benefits Group, expanding the firm's advisory capabilities across the Southeast. Searcy brings more than 20 years of experience spanning employee benefits, HR consulting, technology and process transformation, insurance strategy and organizational development.
"Kristin is a rare blend of strategist, connector, and catalyst who provides transformative solutions to her clients amid a complex business landscape. Her diverse experience and deep connections will provide a powerful strategic advantage to clients from a range of industries," said Kevin Overbey, president of Alliant Employee Benefits.
