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of non-profit boards, and give back to the industry and the
community. In addition, it has been rewarding for me to
serve on the Corporate Board Committee of the Boston Club,
and to help other women get positions on corporate boards
across the country.
What has been the biggest challenge you have encountered?
Like most people, I have encountered several personal and
professional challenges during the course of my career.
While finding and retaining the best talent, and achieving
transformational change would be on my list of top 10 challenges,
my biggest challenge to date is cultivating the entrepreneurial
skills necessary to create a sustainable, prosperous business. I
have found that assimilating and learning from the outcome
of any challenge makes one wiser, stronger and resilient when
encountering future challenges. I also believe that trusting
your gut can be as important as the facts, figures and rational
analyses connected with the challenge.
If you had chosen a different profession/career path, what
would it have been?
Some of my teachers in high school suggested that I would be
an excellent teacher. If I had pursued that path, I would have
followed in the footsteps of my father and uncle, who were
both teachers early in their careers. While in college, I went
through a brief “Jane Goodall” period where I considered
studying anthropology, which I found fascinating.
“Another highlight has been my ability
to serve on a variety of non-profit
boards, and give back to the industry
and the community.”
Elaine A. Caprio
Company: Caprio Consulting
Job title: President
2014: President, Caprio Consulting
2012: Vice president and manager of corporate
procurement, Liberty Mutual Insurance
2007: Vice president and manager of ceded reinsurance,
Liberty Mutual Insurance
1989: Counsel and senior corporate counsel, Liberty
Why did you choose to work in this industry?
It was pure happenstance. I was in my second year of law
school looking for part-time legal work. When my roommate
mentioned there were openings for law clerks at Liberty
Mutual, I applied and was offered a position.
Once at Liberty Mutual, I became attracted to the industry
because of the quality of the people, the interesting work,
and the ability to acquire multiple skillsets and cross-train in
different areas. I appreciated the opportunities to build and
maintain synergistic relationships with other companies and
I have been fortunate to work alongside and learn from some
extraordinary leaders at Liberty Mutual, as well as those
from top law firms, reinsurance companies, intermediaries
What has been the highlight of your career so far?
One highlight of my career is growing and expanding my
own business, Caprio Consulting. I wanted to become an
entrepreneur for many years and was able to realise that
dream a few years ago. In addition to my work providing
insurance and reinsurance operational consulting, and
acting as an arbitrator and mediator to resolve domestic
and international disputes, I have expanded my service
offerings to include gender-balanced leadership consulting
to companies and law firms who understand that in order
to win the war on talent, they must accelerate the pace of
change with achieving gender parity in the C-suite, and on
Another highlight has been my ability to serve on a variety
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