Meet Our
Leadership Team

Rob Sanchez

PRESIDENT

An IT veteran with more than 25 years of experience in large-scale operations and information technology projects in the health insurance sector, Rob provides overall leadership and strategic direction for NorthWinds® and provisions technology services to a number of Delta Dental Member Companies and their subsidiaries.

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Rob is known for sporting NorthWinds gear ALL the time – including in his latest family photo! Originally from Massachusetts, with pitstops in Texas and Wisconsin, Rob, his wife, two kids and old tuxedo cat call Virginia home. He likes to say that Virginia is the “Goldilocks” of weather (not too hot and not too cold). When Rob isn’t working, he enjoys taking his wife (and kids if they’ll join them) out to dinner, weightlifting/running, ...

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Jason Keup

VICE PRESIDENT, CORPORATE SYSTEMS

Jason has 28 years of proven leadership and a wide range of experience in bringing modern technology solutions to several industries. His vast expertise in information technology includes software development, infrastructure, database, security, architecture, and business relations.

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Born in Wisconsin where he still lives today, you’ll find Jason spending his free time doing anything outdoors -hunting, fishing, kayaking, boating, 4-wheeling, snowmobiling, etc. Jason is married and has three daughters. His middle daughter, not pictured in this pre-wedding photo added “Father of the Bride” role to Jason’s skillset. His favorite Fundamental is Do The Right Thing – Always. “I feel that all of our ...

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Amy Bayse

VICE PRESIDENT, IMPLEMENTATION

Amy provides leadership for NorthWinds’ Implementation division, which handles the sale and onboarding of new clients. She has a leadership team covering Business Implementation Services, Business Configuration and Data Migration Services, Technical Implementation Services, Training Services, and Documentation. She brings more than 23 years of benefits, sales, implementation, and healthcare management experience.

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Born in Virginia, Amy still calls the Blue Ridge mountains home, along with her husband Alan and two English Springer Spaniels, Mosby and Lady, named for American historical figures. When Amy isn’t working, she enjoys playing golf with Alan, taking her dogs to the beach, and leading teen and adult Bible study. Amy’s favorite Fundamental is Keep Things Fun. “Life can be tough even on a good day. Keeping things fun rem...

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Randy Ruplinger

VICE PRESIDENT, ENTERPRISE SERVICES

Randy oversees corporate administrative functions including Finance, Human Resources, Legal, Compliance, Audit, Workforce Optimization, and Enterprise Communications. He has more than 30 years of experience in the insurance sector helping organizations achieve their goals with leadership roles in finance, planning and analysis, and actuarial services.

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A Wisconsinite from birth, Randy grew up in a small town in WI, went to college at UW-Madison, and has lived and worked in Madison ever since. Madison is also home to all his children. Trevor and Kayla having gone to college elsewhere and moving back to Madison after graduation and Emily who is currently attending college at UW-Madison. When he isn’t at work, Randy has spent more time than he cares to admit in casinos. He and his wife Jessic...

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Kirk Averett

VICE PRESIDENT, PRODUCT

Kirk has a wealth of experience from more than 20 years leading many different aspects of technology and communication businesses. He builds strong teams that tackle difficult challenges like competing for growth in tough markets, scaling and maturing SaaS platforms, and ensuring long term business financial strength.

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Originally from California, Kirk has called Virginia home for more than 20 years. He is married with seven children including his son-in-law, and one grandchild. Free time? With his size family, what is free time? Being too serious is not an Averett family accusation, as you can see here when the photographer caught them in their natural state during their family photo session. But, Kirk does confess to enjoying video games, relaxing at the lake,...

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Kel Koenig

VICE PRESIDENT, IT SERVICE AND SECURITY

Kel is leading the teams responsible for secure, reliable operations and a consistently strong customer experience. His organization spans Security and Infrastructure, IT Service Management, and System Reliability, with a focus on service delivery discipline, incident readiness and response, platform resilience, and security practices that reduce risk while keeping delivery moving. With 24 years of IT experience, Kel is known for bringing clarity to complex problems, building durable systems, and showing up when it matters most for customers and teams.

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Kel grew up in Iowa, Florida, and Arizona before his family ultimately put down roots in Waunakee, Wisconsin. Fun fact, it is the only Waunakee in the world. He earned his BBA in Management Information Systems from the University of Wisconsin–Eau Claire and returned to the Madison area to launch his IT career.

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