our guess is better than yours.

Meet the Techs

Clayton Cross

It takes a lot of technology to keep a multidimensional operation such as Wayne Halfway House running smoothly, and Clayton Cross is the man with the plan.

Clayton came to WHH in 2021 to help build, expand and modernize the company’s IT department. As WHH continued to grow and additional opportunities emerged to create Guesswork IT Solutions as a standalone managed service provider, he was the obvious person to lead it.

Director of Information Technologies

As director of information technologies, Clayton oversees IT operations for all WHH departments and locations, ensuring systems run efficiently, supporting staff, and implementing new technology solutions across the organization. This includes two facilities in Greenville, S.C., six in Tennessee, as well as all RaeKar, C&B Linen, and Wayne Provision operations, and for external Guesswork clients.

Clayton is a deeply experienced IT professional with specific background in correctional IT. He came to WHH from Wayne County government, where he started as a correctional officer with the sheriff’s department in 2012, but moved quickly into IT for that department and, ultimately, for the entire county. Prior to Wayne County, he worked for 12 years at Comcast Cable, in customer service, dispatch and field service roles.

Clayton and his wife live in Iron City and are the parents of six daughters. He particularly prizes family time with the entire crew, such as regular Sunday dinners with all six children and their families. In his spare time he enjoys woodworking, building and crafting. For vacations, you’re likely to find him and his wife on the deck of a cruise ship!

Rone Simbeck

Information Technologies Supervisor

Rone Simbeck joined the WHH family in 2025 to support information technology needs across the suite of operations, so he was a natural fit when WHH leadership decided to establish Guesswork IT as its own standalone enterprise.

As IT supervisor, Rone divides his time among technical support, system administration and team leadership, keeping key systems running smoothly and coworkers connected. He came to WHH/Guesswork after 11 years at Asurion, where he worked his way quickly up from customer service and tech support roles to, ultimately, Manager of the Endpoint and VDI Operations team.

At Guesswork, he enjoys the opportunity to work with a wide range of technologies – everything from high-level security camera networks and firewall protections to support for smartphones and recreational electronics. On any given day, you may find him training coworkers, handling Microsoft 365 issues, troubleshooting the networked phone system, and any other needs that may arise.

Rone holds a bachelor’s degree in computer science from Tennessee Tech, and he pursues additional training and educational opportunities to keep on top of the latest technological advances and trends. He lives in Lawrenceburg, where he and his wife spend much of their free time at one sporting event or another, with two kids active on travel sports teams and a third just starting T-ball!

Barry Harpending

Account Manager

865-546-9090 | barry.harpending@guessworkit.com

Barry Harpending is the ideal Account Manager for Guesswork IT, bringing with him a potent combination of sales and technical experience.

He started his career as a computer programmer and analyst with Kimberly Clark, before transitioning into outside sales, specializing in telecommunications and IT. He also worked for five years with a medical device

company, marketing specialized wheelchairs for children with disabilities. At Guesswork, he specializes in understanding prospective clients’ technological needs and connecting them with just the right IT solution.

Harpending holds a B.S. from Iowa State University. He’s an outdoor enthusiast, and in his free time you can find him on a hiking trail with his family or working in his garden.