Our Leadership

The BerniePortal leadership team is composed of industry experts with years of experience working together to help organizations across the country keep going and growing.

Alex Tolbert

Alex leads BerniePortal’s day-to-day operations. His entire career has been dedicated to helping HR at small employers succeed in fostering great places to work. Outside of BerniePortal, he serves on the board of Big Brothers Big Sisters of Middle Tennessee and enjoys spending time with his wife and three small children.

Alex received his B.S. and B.A. in Finance and International Studies from the University of Pennsylvania and obtained his J.D. and M.B.A. from Vanderbilt University. He has passed all three levels of the CFA and earned the aPHR designation.

Trennie Williams

Trennie leads our Account Manager team at BerniePortal, which supports our broker partners to distribute the best HR tools and expert solutions that help their employer clients. He is an Eagle Scout and loves the Tennessee Vols. In his free time, he’s training for another marathon race, exploring the city with his wife, or volunteering with the Middle Tennessee Boxer Rescue.

Trennie received his B.S. in Journalism and Electronic Media with a minor in Business Administration and continued his education with an M.S. in Recreation and Sport Management at the University of Tennessee – Knoxville.

Ben Watson

Ben leads research and development efforts at BerniePortal.
His career has taken him through the military, veterinary, fashion, film, and beauty industries before ending up in HR software.Outside of work, he is involved in the music and real estate industries, plays sports, and studies languages.

Ben graduated from Te Herenga Waka in Wellington, New Zealand, with a BSc in Computer Science and a minor in New Zealand Sign Language.

Steven Critchfield

Steven is one of the leaders of the development team at BerniePortal, working to provide first-rate security and performance on a daily basis. His career in software programming has taken him from medical transcription to tracking continuing education, and now, to HR. In his spare time he enjoys building and maintaining both cars and motorcycles, programming for fun, and spending time with his family.

Steven has been building and designing web-based applications professionally for more than 20 years.

Andrew La Haie

Andrew is one of the leaders of the client success team at BerniePortal, which provides customers with expert solutions for their software needs. He is a native Nashville resident and a parent to four young, energetic (and sometimes patience-testing) children. He enjoys doing anything outdoors when it’s warm outside, especially playing golf with friends.

Andrew received his B.S. in Human Resource Management at the University of Tennessee – Knoxville and an M.A. in Higher Education at Florida State University.

Stephanie Sappo

Stephanie leads Finance, HR, People Operations, and Alpine (the sister brand to BerniePortal) at the organization. She has dedicated her career to people development- as she believes service to others is her life mission. Outside of Bernard she serves on the board of Seed India, is active in her church, is a ‘Big Sister’ at BBBS of Tennesse, and enjoys spending time with her family and friends.

Stephanie received her B.S. in Business and is actively pursing her MAcc- with the goal of becoming a CPA.

Anna Baun

With over 15 years of experience in benefits administration and payroll, Anna currently serves as the Director of Client Success at BerniePortal. An alumnus of Indiana University, Anna has a proven track record in enhancing client satisfaction and streamlining operational efficiencies. Prior to joining BerniePortal, Anna held leadership roles at Paylocity and ADP, where she was instrumental in driving team performance and service excellence.

Born and raised in Indianapolis and having spent a significant portion of his career in Chicago, Anna now calls Nashville home with her husband Shawn. This move marked a continued commitment to fostering teams that excel in client service. Anna is passionate about building and leading engaged, motivated teams that consistently deliver exceptional service to clients every day.


Molly Hawkins

Molly is one of the leaders of the Client Success team at BerniePortal, providing Employers with expert solutions for their HR software needs. Molly is originally from Connecticut but has lived all over New England, finding her way to Huntsville, Alabama and currently residing in Nashville.

Molly received a B.S. in Psychology but spent two years in the Culinary program at Johnson & Wales University in Rhode Island. She owned a cafe in Huntsville and is passionate about helping other small to midsize business owners with their HR needs. Outside of BerniePortal, she likes to spend time with her family, friends and cooking.

Sean Furman

Sean is one of the leaders of the sales team at BerniePortal, which provides our prospects with an all-in-one HRIS 100% pro-broker solution. Sean was born in Germany where his family was stationed and moved to the United States shortly after he was born. He grew up in Nashville, TN. In his spare time, he spends time with his wife and two daughters.

Sean graduated from University of Tennessee-Chattanooga with a B.S. in Political Science Legal Studies with a minor in Business Administration.

Katie Shpak

Katie leads the marketing team at BerniePortal. She recently moved from CT, where she lived for almost 30 years, to join us in our Nashville office. She has a B.S. in English and an MBA with a marketing concentration.

Katie has 5 siblings; 3 older brothers and two younger sisters—they were often referred to as “The Brady Bunch”. She is passionate about health and fitness, and in her free time, she enjoys reading, writing, beaching, and traveling whenever possible. 

Jeanine Davis

Jeanine is one of the leaders of the development team at BerniePortal. She is originally from the Chicago area but has been here long enough to remember “old Nashville”. After working in the music industry for a time, a desire for more opportunities and skills led her to pursue a career change to software development. As a former barista also, she is a self-proclaimed coffee snob. Other interests include mentoring teens, staying active, going to concerts and emo nights, and losing to her husband every time in video games.

Jeanine received her BBA in Music Business from Trevecca Nazarene University and later completed the full-stack developer bootcamp with Nashville Software School.

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