Brian Boyd Enables Webster Banks’ Move to the Big Leagues

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Brian Boyd just wanted an Atari. That may not be fully transferable career advice, but it worked for him. Now senior managing director and associate general counsel at Webster Bank, Boyd remembers gently hassling his parents for a gaming system. They responded, as parents often do, not by giving Boyd what he wanted, but perhaps what he needed. Instead of an Atari, his parents brought home a Commodore 64, an 8-bit home computer that was capable of playing games, among other functions.

“I learned to do some very basic programming and developed an appreciation for technology as a kid,” Boyd explains. “My first job out of college was in tech consulting, and I’m not sure I would have wound up there had it not been for that early experience.”

Boyd jokes that his entrance into the job market coincided with the tech bubble of the late 1990s and early 2000s, when, according to the AGC, “They were hiring anyone with a pulse to go into tech.” Boyd worked with large organizations in pharmaceuticals and finance, traveling around, staying in hotels, and running himself ragged. The glow faded after a couple of years, but not before meeting his future wife, sitting next to her by chance on a flight from Minneapolis to Chicago.

All of this is to say, there’s no single path to law school. There are those that have known they wanted to be lawyers since seeing a pivotal film or television show. There are those that had relatives or role models in the law. But there are others, many others, who just needed to find their own way to law school.

Boyd wasn’t sure about a lot upon entering Loyola University of Chicago Law, but he was certain he wasn’t going into litigation. Fate had other plans. The newly minted lawyer’s first significant role was at a litigation boutique. Despite reservations, Boyd immersed himself in commercial litigation, handling contract disputes, liability cases—and notably—intellectual property matters.

The lawyer’s technical acumen made him an asset in the emerging field of electronic discovery, a precursor to today’s data-driven legal practices. Boyd eventually transitioned to a firm with opportunities to a focus on transactional work.  There, he helped establish a dedicated privacy and cybersecurity practice.

A secondment at Pitney Bowes proved fortuitous, giving Boyd the opportunity to work in-house on tech contracts for e-commerce focused on international trade. The experience solidified Boyd’s passion for transactional work and deepened his expertise in tech law.

Boyd joined Webster Bank in 2015 and was promoted to his current role in 2022. The year was a difficult one, with Webster’s merger with Sterling Bancorp, a $10.4 billion deal, which was completed in February of 2022. With that merger, Boyd’s mentor and friend left the organization, among other close colleagues in the department, and Boyd was asked to step up, assuming greater responsibility and helping to integrate teams from both legacy organizations.

“The merger was a merger of equals, which are known to be particularly challenging,” Boyd explains. “It’s been really important for me to build relationships with business leaders across the two organizations to get a better perspective about what we’re working toward and where the businesses’ priorities lie.”

The success of that merger has also created new and interesting work for Boyd. As the organization approaches a $100 billion asset threshold, regulatory scrutiny has intensified. Boyd’s primary responsibilities—leading vendor contracting, intellectual property management, and privacy and cybersecurity matters, have all been impacted. 

Boyd has played a critical role in evolving the bank’s risk management framework to meet heightened expectations from federal regulators, balancing the need for robust infrastructure with the realities of limited resources. The goal is to ensure the bank’s sustainable growth without overextending itself.

“Those new responsibilities have come at the same time I’ve been working with a new general counsel,” Boyd explains of EVP, GC, and corporate secretary Kristy Berner. “Kristy has allowed me to take on some really great new work, and it’s all centered around helping us get to that new level. We don’t just want to eek over that $100 billion threshold, we want to be positioned to jump past it.”

Boyd says that, as a leader, he continues to try and learn patience. The father of three says his Catholic faith is deeply important to him and his family, and it serves as the foundation for him to try and be the best husband, father, and professional he can be. The AGC serves as a board member for the Kids’ Scholarship Fund, a nonprofit that provides scholarships for disadvantaged K-8 students to afford attending a school of their choice.

The morning of speaking with Modern Counsel, Boyd had made it to daily Mass, which he tries to attend as often as he can.

“I think I can be intense, and I can be impatient, and so it’s important for me to remember that you’re dealing with people who are under their own pressures,” Boyd explains. “I have to remember that, while my job is important, lives aren’t at stake, and there is more to life than what’s happening in the office, or the next deadline. Making Mass a day or two during the week just keeps me connected to what’s really the important thing—being a good person.”

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