A DYNAMIC AND MULTIFACETED ROLE

Consider for your approval: A world where everyone was required to stay with their first employer for their entire working career? Where would you be? Is that business even still around today or would you be unemployed? This writer would be struggling. 

My first job was that of a paperboy (also one of my favorite video games), delivering the once-a-week Carmel News-Tribune in my neighborhood, which was conveniently my assigned route. I collected the papers, rolled them up and walked the streets wearing my double pouch carrier bag. I did this for a few years during my latter grade school/early middle school years. It became too much of a hassle in the winter, so I hung up the canvas bag; I think shortly after, another newspaper company bought the one that printed all the smaller suburban editions, and they eventually faded away.

While this writer’s first employer, and a handful after that, are no longer in business, starting out your career with a company where you want to stay sounds divine. For Jordan McKay, marketing and analytics leader at Paradiso Insurance in Stafford Springs, Connecticut, this is what happened.

While insurance wasn’t McKay’s initial focus for a career path, she began her journey at a young age. “I started with the company nine years ago while I was 16 and still in high school, initially handling scanning and preparing birthday cards,” she says. “As I became more involved, my interest in the industry grew.

“What truly drew me in was realizing that insurance is not just a business but a way to protect individuals and their livelihoods. This deeply resonated with me, especially as I pursued my degree in social services, further reinforcing my passion for helping others.” (McKay earned her associate’s degree in 2017 from Manchester Community College.)

As she continued learning about the industry, McKay began working in personal lines before shifting toward marketing, where she has been a leader in that field with the agency for nearly five years.

“My role is dynamic and multifaceted, encompassing a wide range of responsibilities,” she says. “I manage marketing initiatives in collaboration with our SEO team, oversee social media strategy and engagement, and analyze lost and sold premiums to identify client retention trends.

“Additionally, I work closely with [Agency Owner] Chris Paradiso, assisting with community initiatives, mastermind events, and various strategic projects to support the agency’s growth and impact.

“One of our agency’s standout events that I help organize is the annual Flag Day Event on June 14th, which requires extensive preparation, logistical coordination, and community engagement to honor the significance of the day while bringing people together in a meaningful way. My efforts help strengthen connections, promote engagement, and ensure each event’s success.”

Paradiso’s mastermind event is a two-day experience for agency owners and thought leaders to come together for educational sessions, discussion panels and networking opportunities. “I facilitate meetings to ensure that all stakeholders are aligned, fostering collaboration among team members and community partners,” McKay notes.

“A significant part of my responsibilities includes securing necessary permits and adhering to local regulations to ensure smooth event operations,” she adds. “Communication is at the core of my work, as I coordinate with vendors, sponsors, and attendees to create impactful experiences.”

While she assists Chris Paradiso with the mastermind event, McKay enjoys attending them even more. “They provide a valuable opportunity for growth and learning each year,” she says. “The dynamic lineup of speakers and evolving responsibilities within the group ensure a fresh and enriching experience every time. Being surrounded by top industry professionals fosters an environment of continuous development and success.”

Outside the office, McKay volunteers at adoption events with PawSafe Animal Rescue. “It’s a cause that holds deep personal significance for me; I have always had a special place in my heart for animals, particularly those that have been abandoned, neglected, or left without care,” McKay says. “Seeing their struggles reinforces my commitment to helping both animals and people in need, as I continually strive to make a meaningful difference in their lives.”

“Every role within an agency contributes to an

exceptional client experience, and whether you

realize it or not, you are making a difference.”

—Jordan McKay

Marketing and Analytics Leader

Paradiso Insurance

Accolades, advice and free time

Throughout her career, McKay has been fortunate to have many influential individuals who have helped shape her journey. “It all traces back to my parents and my grandfather, who always encouraged me to strive for more,” she says. “Within the industry, individuals such as Chris Paradiso, Stephanie Fanelli, Mike Stromsoe, and many others have played a significant role in my growth. The connections I have made at industry events and conferences continue to provide me with invaluable insights, further fueling my passion and development in this field.”

Some of her personal career highlights include appearing as a guest on the Power Women in Insurance podcast hosted by Teresa Kitchens, and a Thought Leader Thursday episode with Taylor Dobbie. She’s also enjoyed attending esteemed conferences like Mike Stromsoe’s UPP event and having the opportunity to speak about learning an agency’s numbers through pulling reports and auditing at the annual HawkSoft HUG conference in 2023.

For someone new to the insurance industry, McKay’s biggest piece of advice is never to give up. “This industry is full of opportunities—when they arise, seize them,” she says. “Approach every task with dedication, go beyond expectations, and focus not just on the hours you work, but on the quality and completion of your responsibilities.

“Set yourself apart by making a lasting impact, whether through thoughtful gestures like birthday cards, handling administrative tasks with care, or taking the lead in marketing efforts. Every role within an agency contributes to an exceptional client experience, and whether you realize it or not, you are making a difference.

“If you’re on the phone, smile—it can be heard in your voice and might brighten someone’s day. Above all, stay persistent, remain committed, and never stop striving for excellence.”

When she isn’t doing “insurance stuff,” you might find McKay at Stafford Motor Speedway. “It’s a place that holds special meaning for me. My grandfather used to race there. Racing has always been more than just a sport in my family—it’s been a bond, a connection, and a legacy,” she says.

“As my grandfather got older, our love for racing shifted from the track to the couch, where we’d sit side by side watching NASCAR, analyzing every lap, every pit stop, and every checkered flag. Those moments weren’t just about the race; they were about us.

“Since he passed away, I’ve felt the pull to get more involved in racing—not just as a fan, but as a way to keep him close. Every engine roar, every track I visit, every race I watch feels like a way to honor him and the passion we shared. Though he’s no longer here in person, I feel him in the sport, in the speed, and in every heartbeat of the track. Racing is how I keep his memory alive.”

When she isn’t at the track, McKay can be found walking her two rescue dogs—Jager, a German Shepherd and Chow Chow mix, and Stella, a German Shepherd and Australian Shepherd mix—and embracing life’s moments. “I’ve learned to never take life for granted and to always seek opportunities for growth and learning,” she concludes.