High Road PEO sold small businesses something they rarely get from payroll vendors: a human who knows their name. Its 2025 merger with Helpside is a test of whether that intimacy can survive a much bigger operating system.
Founded in 1951 and running quietly out of Vancouver, Washington, BBSI has turned the least glamorous parts of running a business - payroll, workers' comp, HR paperwork - into a $1.2 billion operation built around one idea: put a real local team in the room.
Insperity built a $6.8 billion business by taking on the work small companies cannot afford to get wrong. Now its service-heavy PEO model is being rebuilt for a Workday world.