My Travelers Journey Featuring Software Engineer, Brian Gregg

Travelers Careers promotional image featuring Brian Gregg, Senior Software Engineer. Professional headshot of a man with glasses and curly hair wearing a dark collared shirt, positioned in the lower left corner. The background features an abstract blue digital network design with interconnected lines and nodes representing technology and data flow. Quote text reads: 'At Travelers, I'm valued for asking questions and bringing ideas and I'm learning along the way.' The Travelers red umbrella logo appears in the top right corner, with Travelers Careers branding in white text on red background at bottom left.Brian Gregg’s curiosity started early, inspired by the book “How Come?” by Kathy Wollard, which answers tough science questions for kids. That drive to question and improve became a guiding force in his life and career.

“You never really know how much better things can be until you try and put in the effort yourself,” says Brian, now a Senior Software Engineer on Travelers’ Bond & Specialty Insurance team.

After earning his bachelor’s degree in computer science from the University of Massachusetts Amherst in 2017, Brian began his career as a developer at a software company in Hartford. In 2024, he joined Travelers, where he continues to expand his skills and grow his career.

At Travelers, Brian works in DevOps, blending application development with deployment and management. His role allows him to experiment with cutting-edge technology, support critical systems, and keep pushing for ways to innovate.

It’s a role that suits his mindset. “At Travelers, I’m really valued for asking questions and bringing ideas, and I’m learning along the way,” Brian explains.

Brian’s drive for improvement carries into his personal life too. After the birth of his son in 2021, he pursued a master’s degree in computer engineering from the University of Connecticut, completing it in 2025, as a way to keep developing and set an example for his family.

“I want him to have the best life possible, and I want him to be proud of his dad and his dad’s career. Getting my master’s degree was a great way to work toward achieving both those things.”

Brian’s story highlights how a career at Travelers can offer the chance to build skills, take on meaningful challenges, and continue growing both personally and professionally.

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