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 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 two 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.

Charlie McMackin
Charlie McMackin

Charlie is one of the leaders of the development team at BerniePortal, working to ensure that the platform’s security and performance are top-notch and that the company builds what customers demand as efficiently and effectively as possible. He has been with the company since 2016.

Charlie received his B.S and M.S. in Computer Graphics and Animation from East Tennessee State University.

Ben Watson
Ben Watson

Ben is one of the leaders of the development team at BerniePortal, working to provide customers with outstanding security and performance solutions day in and day out. Outside of work, Ben loves to stay active. He is involved with youth group development and enjoys tennis, volleyball, kickboxing, and rock climbing.

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 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.

Lindsey Van Cleave
Lindsey Van Cleave

Lindsey leads the client success team at BerniePortal. Her team provides trusting operational expertise that helps both our customers and partners succeed with our software. Outside of BerniePortal, she loves to spend her time volunteering with Best Buddies as well as working with the children’s ministry at West End United Methodist Church. When she is not out on the lake with her partner Sam and their two dogs, she loves to cook, workout, and read.

Lindsey received her B.S. in Finance and Statistical Science from the Cox School of Business and Dedman College of Humanities at Southern Methodist University and obtained her M.B.A. from the Lipscomb University College of Business.

Sarah Weinstein
Sarah Weinstein

Sarah leads the sales and marketing teams, which are responsible for creating awareness and demand for BerniePortal’s products and services. Outside of BerniePortal, she enjoys traveling and spending time outside with her dog, Skip.

Sarah received her B.S. in Advertising from Middle Tennessee State University and obtained her M.B.A. from the Lipscomb University College of Business. She has multiple marketing certifications and has earned her aPHR certification.

Brian Tolbert
Brian Tolbert

Brian leads the Bernard Benefits day-to-day operations. Since joining Bernard in 2007, he’s spent his entire time helping employers re-evaluate how they finance employee benefits while also helping them move HR processes online with BerniePortal. Outside of Bernard, he serves on the Nashville Habitat for Humanity Chapter’s Advisory Council and enjoys spending time with his wife and two sons.

Brian received his B.S. from Vanderbilt University and obtained his M.B.A. from the Owen Graduate School of Management at Vanderbilt.

Taylor Dennis
Taylor Dennis

Taylor is one of the leaders of the client success team at BerniePortal, which provides customers with exceptional software solutions. When she is not at work she loves gardening, reading, fitness, and spending time with her boyfriend and their pup.

Taylor received her B.S. in Management and Human Resource Management from the Gary W. Rollins College of Business at the University of Tennessee – Chattanooga. She is aPHR certified.

Trennie Williams
Trennie Williams

Trennie is one of the leaders of the client success team at BerniePortal, which provides our customers with expert solutions for their software needs. Trennie grew up as the oldest of 5 children. He is an Eagle Scout and loves the Tennessee Vols. He volunteers with the Middle Tennessee Boxer Rescue and is a board member with Appalachia: A Southeastern Wind Symphony. In his spare time, he enjoys co-hosting a sports podcast.

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.

Trey Williamson
Trey Williamson

Trey helps lead the Advisor Success Team at BerniePortal, which helps our partners succeed with our software. Before BerniePortal, he helped his mom run a non-profit that taught tennis to special needs children and adults in the Nashville area. In his free time, he enjoys playing golf and tennis. He also enjoys spending time with his girlfriend, along with his friends and family.

Trey received his B.S. in Biology and a Minor in French from Centre College, and he obtained his M.B.A. with a specialization in Healthcare Administration from Bethel University.

Millie Hoffmann
Millie Hoffmann

Millie is one of the leaders of the client success team at BerniePortal, which supports our clients with exceptional software expertise. In her spare time, she enjoys playing tennis and watching the Kansas City Chiefs, as well as hiking and boating with her husband and their dog.

Millie received her B.S. in Business from Missouri State University.

Sarah Hecht
Sarah Hecht

Sarah Hecht leads the people and finance operations that keep BerniePortal going and growing. Sarah is originally from Long Island, NY, but has since moved to Nashville, where she lives with her husband. She is heavily involved in the soccer community in Nashville: she is a member of the Roadies and has previously served on the board for the local organization Kickin’ It 615. In her spare time, she loves to bake, play board games, and listen to podcasts.

Sarah obtained her B.S. in Health Care Administration and her M.P.A from Long Island University – C.W. Post Campus.

Trapp Tubbs
Trapp Tubbs

Trapp leads BerniePortal’s Product Team. His experience in health insurance and product documentation has helped BerniePortal grow into the world-class HRIS software that it is today. When he’s not working with his team at BerniePortal, you can find Trapp volunteering in his neighborhood parks of Lockeland Springs and Shelby Bottoms. He also enjoys playing in local tennis leagues around Nashville and working in his garden.

​​Trapp received his B.A. in English from Sewanee: The University of the South.

Take a look at all our open positions!

Join the team image

Take a look at all our open positions!

Join the team image
Top