Your first hire changes the business — new paperwork, new recurring costs, new compliance obligations. This roadmap sequences the resources that make the transition from solo to employer less overwhelming.
9 resources · 5 free · 4 Tools Club
Before anything else, check whether your current revenue and workload genuinely support this hire — and what cushion you should have first.
Every piece of paperwork and setup step for bringing someone on legally and correctly, in order.
The first-week and first-month plan so your new hire is productive fast instead of guessing what to do.
Track every pay run — gross pay, deductions, net pay — in one place from day one.
If your hire is hourly, you need accurate time records before your first pay run, not after.
Decide and track your time-off policy before it becomes an ad-hoc negotiation with every employee.
Payroll tax is one of the most common places small employers get penalized — track what you owe and when it's due.
If you're offering any benefits, know the fully loaded cost per employee, not just the advertised premium.
Planning beyond the first hire — get a rough sense of which role comes next and at what revenue level it becomes affordable.
This roadmap uses resources from the full library
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