From Military Roots to Meaningful Work at Travelers

For Caleb Earnest, integrity, service and excellence aren’t just words from his time in the U.S. Air Force — they’re values he still lives out every day at Travelers.

Caleb, now Chief Underwriting Officer for Personal Insurance, has been with Travelers for 18 years. He says what first drew him to the Air Force continues to resonate with him in his career today: the opportunity to be part of something bigger than himself.

“All in all together, win together, the commitment to other’s success, collaboration. I’d say the culture has so many common connections to what I experienced in the Air Force,” Caleb shares.

That sense of teamwork and shared purpose made the transition from military service to the corporate world meaningful, though not without its emotions. “While it was my time, and I felt like it was the right time for me to transition into the corporate world, there’s a bit of sadness, because it’s something that had been a part of me and is something that I was committed to and invested in,” he recalls.

Eighteen years later, Caleb says that he has found his place at Travelers, where teamwork and respect continue to define the culture. “I can say now, after 18 years, having been a part of Travelers, that I found my place here.”

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