One of the most common mistakes I see growing companies make: they switch payroll software every time the company hits a new headcount milestone. By the time they reach 50 employees, they've migrated three times and lost institutional knowledge across every transition.
The Starting Point: Gusto (Employees: 8)
At 8 people, Gusto was the obvious choice. Clean interface, fair pricing, handles direct deposit and basic benefits. Everything they needed.
The First Migration: To Rippling (Employees: 22)
The VP of Operations heard that Rippling handled HR and IT in one platform. They migrated at 22 employees to "get ahead of growth." Reality: at 22 employees, they had one HR coordinator and no IT team. The IT automation features sat unused. Rippling cost 3x what Gusto had cost.
The Second Migration: To OnPay (Employees: 31)
After two years of Rippling, the same HR coordinator ran a cost analysis. OnPay offered identical payroll functionality, better built-in HR tools than what they were actually using in Rippling, and cut their annual spend by $8,400.
A Gusto payroll review and alternatives comparison would have surfaced OnPay as the right choice at step one — OnPay's pricing and feature set is often better matched for sub-100 employee companies.
What the Audit Looks Like
Before migrating payroll software: what features are you actually using vs. paying for? What's your per-employee cost at projected headcount in 2 years? What's the real cost of migration?
Most companies that answer those questions honestly realize they don't need to migrate.
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