John Isaksen
John is the Principal, Owner, and original co-founder of Isaksen Insurance, establishing the agency in 1995.
With over 25 years of industry experience, John serves as the trusted anchor of the business. A true people person,
John’s superpower is his ability to connect genuinely with clients, using his naturally jovial attitude to make
everyone feel warm, comfortable, and valued. A resident of the Florida Keys for over 50 years, John has long been
a staple of the Big Pine Key community and remains determined to help his neighbors in any way he can. Today, he
focuses his energy on sales and relationship-building, happily leaving the day-to-day operations in the highly capable
hands of the office’s “Wonder Women.”
Outside of insurance, John has two grown children and is a proud grandfather to six grandchildren and two great-grandchildren,
who always keep him thoroughly entertained.
Paula Isaksen
Paula is the Office Manager, a 220 Licensed Insurance Agent, and one of the original founders of Isaksen
Insurance, which she helped establish in 1995. After taking some dedicated time away to raise her four daughters,
Paula made a seamless return to the helm as an agent to run and grow the company. She is a natural problem solver
who is deeply committed to finding the perfect balance of appropriate coverage and the best possible premiums
for her clients. Guided by a genuine love for customer service, she thrives on answering complex questions and
simplifying the insurance process.
Family is at the heart of everything Paula does; in fact, one of her four daughters works right alongside
her at the agency. Outside of the office, Paula is a passionate volleyball club coach with 15 years of experience
mentoring young athletes. She is also a proud grandmother to two wonderful grandchildren who bring endless joy
and beautiful chaos to her life, and she dearly adores her two sweet Shih Tzu puppies.
Emily Sumner (Isaksen)
Emily is a 220 Licensed Insurance Agent who has been a vital part of the Isaksen Insurance team
for 7 years. Emily’s professional superpower is her deep empathy and intuition; she excels at truly understanding
her customers’ unique needs and takes pride in tracking down the best possible premiums for her clients. Guided
by a genuine love for connecting with people, she thrives on solving problems and figuring out the absolute best
ways to protect what matters most to her community.
Outside of the office, Emily’s life is very fast-paced. She is married to her high school sweetheart, and
together they are raising a son and a daughter. While managing two toddlers, two dogs, and a thriving career
keeps her schedule packed, she loves to sneak in a good book or clear her mind with a kickboxing session whenever
she gets the chance.
Jennifer Cunningham
Jennifer is the friendly face and organizational powerhouse behind the front desk at Isaksen Insurance.
Joining the team in December 2021, Jennifer specializes in the art of the multi-task—expertly managing
client communications, assisting agents with new business and renewals, and seamlessly handling phone,
emails and updating mortgages on policy’s.
Driven by a genuine love for helping others and working in a fast-paced environment, she consistently
strives to go above and beyond for both her clients and her co-workers. She is currently leveling up
her expertise by working toward her insurance license so she can begin writing policies directly.
Originally from Georgia, Jennifer relocated to the beautiful Florida Keys in 2019. Outside of
the office, she is a proud mama to an energetic 4-year-old son, and she loves nothing more than
watching him learn, grow. She has a love for the beach, visiting Georgia, traveling and making magical
memories at Disney with her son.
Business Statement
Living in the Florida Keys is truly paradise, but owning property here comes with unique responsibilities
and challenges—especially when it comes to navigating the complex insurance market. We understand that
choosing the right insurance agency is an important decision, and at Isaksen Insurance, we believe exceptional
service starts with putting our clients first.
We treat every client like a neighbor, taking the time to understand your needs, explain your coverage options
clearly, and help you make informed decisions with confidence. As an independent agency, our loyalty is to
you—not a single insurance carrier. That means we work on your behalf to find coverage solutions that protect
what matters most while providing the peace of mind you deserve.
When you partner with Isaksen Insurance, you can expect transparency, honesty, dependability, and the local
expertise that comes from serving the Florida Keys community. We're committed to helping you protect your home,
your property, and your future with personalized guidance every step of the way.
