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The DIG Team

Brad Dees

Brad Dees

Principal Agent/Co-Founder

Brad was born and raised in Auburndale, FL. After hanging up his baseball cleats (and catcher’s gear)...

Kathrine Pienkos

Kathrine Pienkos

Insurance Advisor

Kathrine started her life in Chicago and grew up playing many sports like baseball, basketball, soccer...

Samantha Kirkwood

Samantha Kirkwood

Insurance Advisor

Born and raised in St. Petersburg, FL (near Treasure Island Beach), Samantha played in a semi-pro...

Kendra Wells

Kendra Wells

Sr. Account Manager

Kendra moved to Florida in April 2015 from The Bluegrass State of Kentucky, where she owned a craft ...

Jake Little

Jake Little

Commercial Account Manager

Born in Port Charlotte and raised in Punta Gorda, Jake now calls Sarasota home. He joined The DIG Team in...

Now Hiring (Account Manager)

Now Hiring (Account Manager)

(Hiring) Account Manager | Personal Lines

Apply today--you deserve it! Click "read more" for detail on this position and to apply...

This Could Be You

This Could Be You

Join The DIG Team

Have you been craving a career in a stable industry with a growing team who is fun and top rated?

Julia Dees

Julia Dees

Marketing Director/Co-Founder

Julia was born and raised in Venice, FL. After graduating from Florida State University and meeting her ...

Paola Pomfret

Paola Pomfret

Insurance Advisor

By way of Orlando, Paola joined the DIG Team in January 2020. Having started her career in fashion...

Amanda Lade

Amanda Lade

Insurance Consutant

Amanda is a rare local—born and raised in the Sarasota. Having graduated from Booker Highschool's...

Kammy Sproul

Kammy Sproul

Account Manager | Personal Lines

Born in Ohio and raised in the Bradenton area since she was seven, Kammy grew up on a deer farm...

Katie Scheid

Katie Scheid

Account Manager | Personal Lines

Katie is a Sarasota county native, growing up in Venice, FL. She previously was a part of...

Now Hiring (Licensed Insurance Agent)

Now Hiring (Licensed Insurance Agent)

(Hiring) Licensed Insurance Agent

Apply today--you deserve it! Click "read more" for detail on this position and to apply...

Courtney Grover

Courtney Grover

Managing Agent

Courtney is a rare local—born and raised in the Sarasota Area. She graduated from the University of...

Jacob Cooper

Jacob Cooper

Insurance Advisor

Born and raised in the Sarasota-Bradenton area, Jacob continues to call this area home. He joined the DIG...

Rachel Matichak

Rachel Matichak

Insurance Consultant

coming soon...

Kailey Shenk

Kailey Shenk

Account Manager | Personal Lines

Kailey moved to Florida from Colorado in 2017 and joined The DIG Team in April 2023. She joins us by way of...

Angela Neely

Angela Neely

Insurance Coordinator

coming soon...

Now Hiring (Insurance Sales Agent)

Now Hiring (Insurance Sales Agent)

(Hiring) Insurance Sales Agent

Apply today--you deserve it! Click "read more" for detail on this position and to apply...

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