WIN Magazine - Fall 2017 - 40

IN THE WIN-NER'S CIRCLE

7-MINUTE READING TIME

ERIN O'LEARY

In the WIN-NER's Circle
Underwriting Discipline One Stroke at a Time

E

RIN O'LEARY BEGAN HER
insurance career with
Shelly,
M iddlebrooks
& O'Lear y based in
Jacksonville, Florida, in
2003 after graduating from
Agnes Scott College with a degree in
business economics. Her early responsibilities within the wholesale managing
general agency were in the commercial
transportation sector of the business
and this has remained her underwriting
focus over the years. As a shareholder
and vice president her responsibilities
beyond underwriting include the training and professional development of
new employees.
She holds the Accredited Advisor
in Insurance and Transportation Risk
Specialist designations and, outside of
the agency, she serves as president of
the Florida Surplus Lines Association
and a member of The Women's Board of
Wolfson Children's Hospital.
Erin's grandfather founded the insurance operation in 1952 with a purpose
to serve the independent agents in the
southeast with excellent service. For
over 60 years their specialty has been
underwriting transportation, commercial liability, professional liability
and personal lines. Erin has a fascinating life both within and outside of her
professional activities. We recently sat
down to get her unique perspectives and
how she keeps her balance between her
insurance life, and something else about
which she is very passionate.
WIN: What is it that drew you to
become an insurance professional? And
what about the industry do you enjoy
the most?
O'Leary: After college, I knew I wanted
to pursue a career in business. My dad
offered me the opportunity to work in

4 0 | F A L L 2 0 17 | W I N M A G A Z I N E

Erin O'Leary swims the Strait of
Gibraltar in 2016

I was
the agency and make the decision after
a year if insurance might be an industry
I enjoyed. I had always admired my dad
and embraced the opportunity to work
with him. I enjoy providing solutions
for customers or promoting efficiency
within the agency.
WIN: We understand you have a
rather unique hobby - can you tell us
about it, and how you got started in it?
O'Leary: Swimming competitively has
always been a part of my life and I excel
in distance events. After college, I joined
a master's swim team, which trains in
the pool during the week and swims 3
to 6 miles in the ocean on the weekends.
Open water swimming was a natural progression; I love the freedom of no lines,
no lane ropes and no walls. The sport
attracts a positive community of people
and provides an opportunity to combine
my passion for travel and swimming.
WIN: You've done some incredible
long-distance swims already. How do
you decide where you want to go, and
how do you train for the swims?
O'Leary: The popularity of the sport
exploded in the past decade with swimmers focused on completing the Ocean's

terrified to
swim at night with a
chemlight, especially after
a family member made a
point of telling me that bright
lights are used when fishing
to attract bait fish, which
attract bigger fish.

Seven, which consists of seven marathon swims around the world including:
the North Channel, the Cook Strait, the
Molokai Channel, the English Channel,
the Catalina Channel, the Tsugaru Strait
and the Strait of Gibraltar. The waitlist
for these swims averages four years.
Today, swimmers are also charting
their own course. This summer Sarah
Thomas was the first athlete to complete a century swim, 104.6 miles, in
Lake Champlain that took over 65 hours.
WIN: Well, it looks like you've started
on the challenge by having just finished
swimming across the Catalina Channel
in September. What was that like?



Table of Contents for the Digital Edition of WIN Magazine - Fall 2017

Do Hurricanes Have a Silver Lining?
Underwriting Marijuana
The Cyber Insurance Conundrum
Writing Data Security Into Law
Gauging Risk, Reaping Reward
Simply Seamless
Moving to the Cloud: 3 Migration Strategy Models and the 6 R’s.
In the WIN-NER’s Circle
WIN Magazine - Fall 2017 - Intro
WIN Magazine - Fall 2017 - bellyband1
WIN Magazine - Fall 2017 - bellyband2
WIN Magazine - Fall 2017 - cover1
WIN Magazine - Fall 2017 - cover2
WIN Magazine - Fall 2017 - 3
WIN Magazine - Fall 2017 - 4
WIN Magazine - Fall 2017 - 5
WIN Magazine - Fall 2017 - 6
WIN Magazine - Fall 2017 - 7
WIN Magazine - Fall 2017 - 8
WIN Magazine - Fall 2017 - 9
WIN Magazine - Fall 2017 - 10
WIN Magazine - Fall 2017 - 11
WIN Magazine - Fall 2017 - Do Hurricanes Have a Silver Lining?
WIN Magazine - Fall 2017 - 13
WIN Magazine - Fall 2017 - 14
WIN Magazine - Fall 2017 - 15
WIN Magazine - Fall 2017 - 16
WIN Magazine - Fall 2017 - Underwriting Marijuana
WIN Magazine - Fall 2017 - 18
WIN Magazine - Fall 2017 - 19
WIN Magazine - Fall 2017 - 20
WIN Magazine - Fall 2017 - 21
WIN Magazine - Fall 2017 - 22
WIN Magazine - Fall 2017 - 23
WIN Magazine - Fall 2017 - The Cyber Insurance Conundrum
WIN Magazine - Fall 2017 - 25
WIN Magazine - Fall 2017 - Writing Data Security Into Law
WIN Magazine - Fall 2017 - 27
WIN Magazine - Fall 2017 - 28
WIN Magazine - Fall 2017 - 29
WIN Magazine - Fall 2017 - 30
WIN Magazine - Fall 2017 - Gauging Risk, Reaping Reward
WIN Magazine - Fall 2017 - 32
WIN Magazine - Fall 2017 - 33
WIN Magazine - Fall 2017 - 34
WIN Magazine - Fall 2017 - 35
WIN Magazine - Fall 2017 - Simply Seamless
WIN Magazine - Fall 2017 - 37
WIN Magazine - Fall 2017 - Moving to the Cloud: 3 Migration Strategy Models and the 6 R’s.
WIN Magazine - Fall 2017 - 39
WIN Magazine - Fall 2017 - In the WIN-NER’s Circle
WIN Magazine - Fall 2017 - 41
WIN Magazine - Fall 2017 - 42
WIN Magazine - Fall 2017 - cover3
WIN Magazine - Fall 2017 - cover4
WIN Magazine - Fall 2017 - outsert1
WIN Magazine - Fall 2017 - outsert2
WIN Magazine - Fall 2017 - outsert3
WIN Magazine - Fall 2017 - outsert4
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