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.
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.
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.
Jake Vitatoe
Jake leads sales at BerniePortal, which provides our prospects with an all-in-one HRIS 100% pro-broker solution. Jake is originally from Kansas City, where most of his family still resides. After a stint of playing professional baseball in the Caribbean, Jake became a licensed insurance agent specializing in Medicare with a plethora of knowledge in the Health & Life space. He has nearly a decade of sales experience that he brings to the team here at BerniePortal. Outside of work, he loves hitting the gym, going on hikes, and checking out any and all live events/concerts.
Jake graduated with a B.S. in Criminology along with a B.S. in Statistical Mathematics from the University of Missouri-Kansas City. He is an avid sports fan and loves his Kansas Jayhawks and Dallas Cowboys (Don’t hold that against him).
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.
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.