MEET THE DULUTH TEAM
Theresa Caine, CISR - Senior Personal Lines Account Manager
Theresa is a Senior Personal Lines Account Manager who works with educating clients on their insurance needs and how to meet those needs. She knows that insurance can be confusing and enjoys explaining insurance to make it understandable. Theresa holds a BA in Secondary English Education from UMD and has worked in the insurance industry since 1997.
She obtained her CISR (Certified Insurance Service Rep) certificate in 2012. Theresa enjoys spending time with friends an family. She and her husband Jeremy) along with their two daughters are avid fans of Disney and enjoy visiting Disney World every chance they get.
Sarah Erickson - Controller
Sarah has been with J3 Insurance since 2007 and is one of the newest owners of J3 Insurance. She enjoys working with J3’s staff to consistently provide the best service to our clients. She believes that insurance isn’t always about price but rather what is the best coverage for each client’s unique needs.
Sarah is licensed in Property & Casualty Insurance and also holds a BFA degree from the University of Minnesota Duluth. In her spare time she enjoys the outdoors, fishing from her kayak, all things fiber arts as well as training her dogs in obedience, rally, agility, and nose work. She also volunteers as a trainer at a local dog training club and volunteers with her certified therapy dog at local hospitals, colleges, and other facilities.
Kay Shipka - Senior Personal Lines Account Manager
Key is a Senior Personal Lines Producer Licensed in MN and WI with 20+ years of Insurance experience.
Kay’s main goal is to try and simplify the insurance process so customers can understand what they are buying, and why they need it. She previously owned her own Insurance Agency in Duluth for 12 years, and then lived in South Florida for 2 years working as an Insurance Account Representative. After moving back home to be closer to her family, she happily joined our team in 2016.
Outside of work, Kay, and her Husband, Chuck, like to ATV, take trips, cook, and hang out with friends, and family. They also enjoy sharing their spare time with their Rat Terrier named Jack.
Christina Schleicher, CIC - Senior Commercial Lines Account Manager
Christina is a Senior Commercial Lines Account Manager,
licensed in Property & Casualty. She obtained her CIC (Certified Insurance Counselor) designation in 2025 which she is very proud of.
Christina strives to ensure all of her clients are fully protected.
She specializes in finding creative solutions for “out of the ordinary” situations. Christina grew up in the Twin Cities with a background in social work, contributing to her caring and understanding when the unexpected happens. Outside of J3, Christina spends time with her family and 3 Australian Shepherds hitting the outdoors.
Christina, her family, and their dogs have been mile by mile conquering the entire Superior Hiking Trail.
Jason McCaffrey -
President
Principal/Agent
His goal is to make business and personal insurance understandable, allowing clients to make wise risk transfer decisions when it comes to home, auto, business, life & health insurance. Jason started his insurance sales career 20 years ago at a large independent agency in Madison, WI. Jason currently serves on the Board of Directors at the Boys & Girls Clubs of the Northland & Foundation. He is a past President of the Madison East Rotary Club.
Jason is a proud husband (Dr. Diane) and father (Jack Peter & Alli Hazel) who enjoys spending time with his family & friends at various sports events as well as hanging at the cabin (summer) or somewhere warm (winter.) In his spare time, he enjoys building his real estate portfolio and living life in the communities he serves.
Jeff McCaffrey, CPCU-Vice President
Principal/Agent
Jeff started his career in 1992 as an underwriter in Personal lines Insurance for a regional carrier in Wisconsin. After a year, he joined a larger carrier in Minnesota as a Commercial Lines Underwriter. In 1998 he was promoted to Marketing Rep for the Twin Ports & Northern Minnesota. In 2004 Jeff left the “company side” of the business for the “agency side” by joining a local Independent Agency. Later that year, he founded Twin Ports Insurance and in 2018 the agency re-branded into J3 Insurance. Jeff enjoys helping clients solve problems loves everything about insurance. Jeff has a Bachelor of Science Degree from the University of Wisconsin – Stout where he majored in Applied Math and Actuarial Science. He obtained his CPCU designation in August of 2000.
Jeff enjoys sports — especially watching his nieces and nephews games. He also enjoys spending time with friends and family. He believes this year is the Vikings year.
Sylvia Messer, CISR - Senior Commercial Lines Account Manager
Sylvia received her license in 2018 when she joined the J3 team. She assists Commercial clients with their insurance needs. She prides herself in making sure coverages are accurate and clients needs are met.
When not helping out clients, Sylvia enjoys spending time and getting outdoors with her family.
Sylvia obtained her Certified Insurance Service Representative certification in 2024
Steve Mason -Agency Manager
Steve is currently our Agency Manager for all 3 of our locations. Steve comes to J3 with over 16 years of experience in Insurance. He enjoys helping his clients truly understand the coverage their policy provides, which enables him to assist clients in protecting their assets in the most financially responsible way.
When not servicing customers he enjoys traveling, playing video games, hiking, and spending time with his family.
Megan Ramsdell - Personal Line Account Manager
Megan joined the J3 team in 2020 and obtained her Property and Casualty licensing in 2021. She has 3 years of experience in the industry and strives to make sure cutomers needs are met. Megan understands the importance and enjoys making sure you are adaquatley covered for all of lifes curveballs.
When she is not in the office, Megan enjoys spending time outdoors with her family and exploring all the twin ports has to offer.
Megan looks forward to assisting clients.
Hunter Bergerson - Producer/Licensed Agent
Hunter grew up in Duluth playing hockey and going to school at Duluth East. After high school, he played a year of Junior hockey in Minot, ND before attending The College of St. Scholastica, where he played hockey and double majored in Finance and Management. He is married to his longtime partner, Kali, who is also from Duluth. Hunter stays involved in the community coaching hockey in Hermantown and being an active in the Duluth Area Chamber of Commerce programs. Professionally Hunter is very passionate about helping people and building strong relationships with his clients.
Carley Byrnes - Personal Lines Representative
Life & Health Service Representative
Carley comes to J3 after a successful, 6 year career in the healthcare industry. Originally from SW Minnesota, Carley has called the Twin Ports her home since 2014. Recently married to her husband Jarret, Carley resides in Superior, WI with their two furry companions, Riley and Sadie. With a passion for helping people, Carley looks forward to building a fulfilling career in the insurance industry as an independent agent.
Carley enjoys playing sand volleyball with her close friend group and spoiling her nieces and nephew. She also loves watching and going to hockey games.
Erin Thompson - Personal Lines Service Representative
Erin has recently joined J3. She currently has a bachelor’s degree in psychology, Erin brings a keen eye for detail and a deep understanding of client needs. She recently obtained her Property and Casualty license and is eager to assist our clients in finding the best insurance solutions.
Erin is a proud native of Superior, WI, where she lives with her boyfriend, Jared, and their five-year-old Goldendoodle, Ole. When she’s not at work, you’ll find her enjoying a round of golf, playing softball, diving into a good book, or spending time at her family cabin. Erin also loves spontaneous adventures with her sisters and friends.
Keaton Bergerson - Personal Lines Service Representative
Keaton joined the J3 team in September of 2024. He currently has a bachelor’s degree in marketing from NDSU. He recently obtained his Property and Casualty license and is excited to assist clients with their insurance needs.
Keaton is a Duluth native having graduated from Duluth East. When not at work he enjoys being with his friends, playing a round of golf, visiting the local breweries, exploring the hiking trails around Duluth and being up at the family cabin.
MEET THE CLOQUET TEAM
Dana Dandrea - Senior Commercial Lines Account Manager, CISR
Dana obtained her State of MN Property, Casualty, Health, and Life License in the Spring of 2007. She has recently completed her Certified Insurance Service Representative Designation.
Dana understands that each business has unique insurance needs and she works with clients to find the best coverage with the most affordable rate. Dana was born and raised in the Northland and is an avid Vikings and Wild fan. Her favorite pastime is spending time with friends and family on the lake and her greatest joy is being a grandma to her two beautiful granddaughters.
Michelle Youngberg - Senior Personal Lines Account Manager
Matt Ostby - Producer/
Licensed Agent
Karly Rasmussen - Personal Lines Account Manager/Commercial Lines Service Representative
Karly is a Personal Lines Account Manager who believes in hard work to maintain competitive insurance rates that can and should be customized to fit your specific needs. No one can surely predict the future, but Karly is here to help you protect it! Prior to joining J3 Insurance she has 8 years of extensive customer service relations. She earned her State of MN Property and Casualty license in the spring of 2019.
For fun, she loves trying new things, spending time at the sand volleyball courts, and of course with her animals, friends, and family.
Nikki Skramstad - Personal Lines Account Manager
Nikki graduated from UW- Superior with a Bachelors Degree in Communications Management. She brings many years of customer service experience to J3.
Outside of work she enjoys spending time with her husband Mark and their 3 daughters; Emma, Maci, & Chloe. When she isn’t watching her daughters play hockey or soccer, she enjoys traveling to Florida, spending time on their boat, shopping and hanging out with family and friends.
Joe Beaupre, CIC -
Vice President of Sales
Principal/Agent
Rachel Malzahn Personal Lines Service Rep
With a dynamic career spanning nine years in the health insurance industry, Rachel has continually demonstrated a passion for learning and professional growth. Motivated by a desire to broaden her expertise, she recently diversified her skill set by venturing into the realm of property and casualty insurance, achieving licensure in the summer of 2023.
Originally hailing from Minneapolis, Rachel chose Duluth as her home in 2008. Beyond her professional endeavors, she finds joy in creating lasting memories with her children and family during the summer months at the lake. An avid enthusiast of outdoor activities, she delights in swimming, fishing, and competing in a local cornhole league.
Rachel’s interests extend beyond the lakeside, she enjoys cooking. Her downtime is often filled with friendly competition, whether engaging in board games, attending concerts, or enjoying a night of stand-up comedy. Rachel is renowned trivia whiz.
MEET THE BRAINERD LAKES TEAM
