A Byte-Sized Tech Chat with Garret Droege, CIC


Awkward Insurance hosts Dustyne Bryant and Ashley Fitzsimmons have a fun conversation with Garrett Droege, CIC Director of Innovation and Digital Risk Practice Leader at IMA Financial and Co-Founder of IMA web3Labs, about beautifully complex concepts around web3, insurtech, and machine learning technologies in an effort to understand how these concepts may apply to the insurance industry and independent agents and agencies in particular. Believe it or not, you may already have a “tech-stack” in your agency, so the next step forward may not be as concerning as you think.

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Garrett Droege, CIC, CPCU, CLCS, CBIA, CWCA, CRIS 

Senior Vice President and Director of Innovation and Digital Risk Practice Leader at IMA Financial

Garrett Droege serves as Senior Vice President and Director of Innovation and Digital Risk Practice Leader at IMA Financial. His role oversees IMA’s national focus in the technology, and digital risk verticals (collectively called the Advanced Industries Specialty). He also co-manages IMA Labs, IMA’s insurtech innovation, investment, and strategy with BrokerTech Ventures. Additionally, he is part of the founding team of IMA’s web3Labs initiative and helped IMA become the first broker to build an insurance and risk management facility in the metaverse and issue the industry’s first “proof of coverage” via blockchain/NFT. He serves on the Crypto.Chicks NFT Advisory Board and consults with several other NFT projects.

Prior to his current role, he served as CEO/Executive Director of TechAssure Association, Inc., an international consortium of insurance agents/brokers specializing in technology-related risks. Garrett’s expertise includes Errors & Omissions, Cyber, and Technology Risk Management. Additionally, he is a brokerage technology specialist – focused on InsurTech, AMS/BMS/CRM platforms, data mining, and client journey tech stack development.

Garrett has designed complex insurance and risk management programs for some of the most sophisticated and diverse tech businesses in the country. These include firms in info tech, medical technology, telecommunications, new media and all types of digital risk and blockchain.

Garrett is an alumnus of University of North Carolina at Wilmington and The Hartford School of Insurance. He was named to the Charlotte Business Journal’s 40 Under Forty list and Insurance Business America’s Young Guns of Insurance list. Garrett is routinely featured in national publications and media productions, including NPR’s All Things Considered.

He holds the esteemed Chartered Property Casualty Underwriter (CPCU) and Certified Insurance Counselor (CIC) industry designations, among others. He has been a featured keynote speaker for numerous organizations, including: Federal Bureau of Investigation, National Public Radio, CIO Magazine, Society of CPCU, Insurance Innovators, FinTech Association of Hong Kong, Net Diligence, Healthcare Information & Management Systems Society (HIMSS), Information Systems Audit and Control Association (ISACA), North Carolina Technology Association, Texas Blockchain Council and many more.


Droege has been named three times to the Hot 100 List – a group of the top 100 insurance professionals that have “moved the industry forward” over the past 12 months. Garrett also serves as an advisor and mentor to several technology startup companies and has extensive relationships with global accelerator programs and investors. He is a frequent guest on business podcasts including: “The Insurance Guys”, Lowenstein Sandler’s “Don’t Take No For An Answer,” “InsurTech Geek Podcast,” “Beyond Insurance,” “A.I. Wisdom,” “The Insurance Coffeehouse,” and more.

Dustyne Bryant, MBA, CIC, CISR

Personal Lines Academic Director & Awkward Insurance Co-Host

Dustyne Bryant,  is the Personal Lines Academic Director for The National Alliance for Insurance Education & Research. In her role, Dustyne collaborates with National Alliance faculty and industry colleagues to research and analyze Personal Lines segment trends, data, and coverage in an effort to deliver relevant and quality educational content to growing insurance professionals. 

Ashley Fitzsimmons, CISR

Director of Professional Development, Ohio Insurance Agents Association, Inc.

Awkward Insurance Co-Host

Known as the Beyonce of Insurance, Ashley has grown up in insurance. She has real life experience on the agency side – for nearly the last decade. She has had to overcome the same daily struggles and has personally researched and implemented many tools and programs to help her family agency run more efficiently.

Nine years spent as the fourth generation in a family agency located near Scranton, PA, obtaining her CISR designation, multiple speaking engagements across the country as well as being nominated the 2018 National CSR of the year has given her the knowledge and experience to help other agents thrive instead of just survive.

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