From Awkward to Awesome: Leadership and Insurtech


In this episode of Awkward Insurance, hosts Dustyne Bryant and Ashley Fitzsimmons kick back with Megan Kuczynski, President of Insurtech Insights USA, to chat about Megan’s rise to leadership. They dive into the idea that everyone’s career journey is different and there’s no need to constantly compare yourself to others. Plus, they unpack the vital role Insurtech conferences play in introducing tech advancements to the insurance industry and the life and health niche that excites Megan.

Megan Kuczynski

Megan Kuczynski has over 20 years of senior management experience at the top global business media companies including United Business Media (Informa), Penton Media, Diversified Communications, and Reed Elsevier.

Megan has led Trade show 200 city-wide conventions, vertically themed events, and exclusive invite-only CXO conferences in domestic and global markets. She has a proven track record in growing technology portfolios and is skilled in launching new businesses as well as acquisitions.  The theme of Megan’s career has centered around disruptive technology. Recently, Megan served as President of Insurtech Connect (ITC). Under her leadership, the conference was awarded Trade show Executive’s Fastest 50, a recognition of the fastest growing events held in the U.S.  In January, the largest global network of insurance professionals, entrepreneurs and investors, London-based Insurtech Insights, appointed Megan President of Insurtech Insights USA, and with that appointment came the announcement that ITI has chosen Stamford, CT as its U.S. headquarters. Megan will focus on building Insurtech Insights USA and its annual conference in June at the Javits Center in NYC.  Megan is a frequent speaker at international conferences and the author of bi-monthly Insurtech Talks for Modern Insurance Magazine.  Megan lives in Stamford with her husband Tom, two teenage sons, and two King Charles Cavalier spaniels. In her spare time she enjoys racquet sports and sailing.

To hear more valuable insights register to attend InsurTech Insights NYC with an exclusive Awkward Insurance discount code!

Over 5,000 industry leaders, entrepreneurs and investors will take over the Javits Center for two days of insights, inspiration and networking.  Hear from over 400 speakers and over 500 companies in the expo hall on the most electrifying advancements in insurance innovation.   

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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