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Keep Asking “Why?”


Bobby and his family
Bobby and his family

Q: What were your interests and studies at Hamilton College, and how did those experiences prepare you for your current career?

A: At Hamilton I majored in math, minored in English, and rounded that out with a variety of other coursework (computer science, economics, even a photography class to get that liberal arts experience). Far-and-away, the most important aspect of all my Hamilton experiences was that I was able to further develop my critical thinking skills. If we're being honest, most of the actual coursework a student completes as an undergrad is not going to come in handy in their career (I have never found a solution at work by cracking open my abstract algebra textbook and formulating a proof). But having the ability to focus your innate curiosity to pursue answers to challenging problems is useful in a variety of fields, and that is a skill students practice every day.

Q: What do you find the most challenging about your job? What do you find the most rewarding?

A: For me, the most challenging aspect of my role is managing a team. For the first six years of my career, I worked in research and data science rules as an individual contributor. This is a pretty natural transition from being a student, since 99% of your ability to be successful is fully within your control. When you move into managing, you have to put a lot of trust in your team to do their work up to your standards, recognizing that they will all approach solutions differently. I think I have gotten better at this over time (I started managing in 2013), but it's still a much different sort of challenge than the quantitative problems I'm more comfortable with.

Q: What motivated you to seek this career path?

A: Not a great answer here. I worked for about 18 months at Pratt & Whitney in the research center after graduating. My girlfriend at the time (now wife) really wanted to leave Connecticut and move to New Hampshire where her family is from, so I looked for companies in the area hiring analytic roles and found Liberty Mutual. I guess that just shows how fungible the STEM toolkit is, since making a career change from a defense contractor to an insurance company was really easy.

Q: What advice would you give to current Hamilton students thinking of pursuing this field?

A: The standard advice I give is to lean in to your curiosity. Don't accept the first answer you get, but keep digging deeper and asking “why?” A common problem insurance companies face coming out of the pandemic is that the amount of claims we are paying is increasing at a very  high rate. If you accept a surface-level answer to that question (like, “people are crashing more”) you won't come up with good solutions to the problem. But if you keep digging you'll uncover a multitude of factors (people are driving more and driving patterns have shifted away from rush hour; used car inventory is low due to global chip shortages; the profile of a commuter has shifted as many office jobs are now fully remote; etc.). Individuals who approach problems with the  mindset of wanting to leave no stone unturned are generally going to be successful in analytic roles.

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