SimpleStaff vs When I Work
When I Work is polished and popular, but it charges per user on every plan — so the bill grows with every hire. SimpleStaff keeps a low base and a small per-user rate, and stays far cheaper as you grow.
When I Work is a mature, well-liked scheduler. The catch is pricing: every plan is per user, so your bill scales straight up with headcount, and time tracking costs extra per user on top. SimpleStaff includes your first 15 people in a low base and adds only a small per-user rate beyond that — usually less than half the price once you pass 15 staff.
What you'd actually pay
| Scenario | When I Work | SimpleStaff · Team | SimpleStaff · Pro |
|---|---|---|---|
15 staff | $37.50 Essentials ($2.50/user) | $19/mo −49% | $29/mo |
30 staff | $75.00 Essentials ($2.50/user) | $30.25/mo −60% | $44/mo |
60 staff | $150.00 Essentials ($2.50/user) | $52.75/mo −65% | $74/mo |
When I Work Essentials list price of $2.50/user/month, their entry plan, from wheniwork.com/pricing (July 2026); Pro and Premium cost more, and time tracking is an added per-user charge. SimpleStaff figures are computed live from our plans, with the first 15 users included in the base.
Why the gap widens as you grow
Per user on every plan
When I Work charges for each person on every tier, so 30 people cost twice what 15 do. SimpleStaff includes the first 15 in a low base, then adds a small per-user rate — the curve is far flatter.
Time tracking costs extra
On When I Work, time and attendance is an added per-user fee on top of the plan. With SimpleStaff it's an optional add-on you only pay for if you want it, on the same pooled seat count.
Unlimited, pooled, no tier jumps
One subscription pools every location, with no employee cap to push you up a tier. You grow your team without watching a per-seat meter climb.
Feature by feature
| SimpleStaff | When I Work | |
|---|---|---|
| Drag-and-drop scheduling | ||
| Staff-run shift swaps | ||
| Availability & time-off requests | ||
| Mobile app (iOS & Android) | ||
| Free plan (not just a trial) | ||
| Low base with first 15 users included | ||
| Time & attendance | Add-on | Add-on |
| Seniority-based shift picking | Pro | |
| Built-in payroll | Pro | Add-on |
| Starting price · 15 staff | $19 / mo | $37.50 / mo |
When When I Work might be the better fit
- You want its specific strengths in labour forecasting and built-in team messaging.
- You run a very small team where a per-user rate barely registers.
- You're already invested in the When I Work ecosystem and its integrations.
Common questions
Is SimpleStaff cheaper than When I Work?
For almost any team past a handful of people, yes. When I Work charges $2.50 or more per user on every plan, so 30 staff is about $75/month. SimpleStaff includes your first 15 users in a $19 base and adds a small per-user rate beyond that — usually less than half the total.
Does When I Work have a free plan?
When I Work offers a free trial rather than a permanent free plan. SimpleStaff is free for up to 15 staff for as long as you like, so you can run a real schedule without paying.
Is time tracking included?
On When I Work, time and attendance is an added per-user charge. On SimpleStaff it's an optional add-on billed on your pooled seat count, only if you enable it — otherwise you don't pay for it.
Can I switch from When I Work easily?
Yes. You can set up your team, build a week, and publish in minutes — free for up to 15 staff — so you can trial it beside When I Work before committing. No credit card required.
The cheapest way to find out is to try it
Set up your team, build the week, publish. Free for up to 15 staff — run it beside your current tool before you spend a dollar.
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