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Most buyers should pick Deputy.
Choose Deputy if compliance, HR tools and a Paycor payroll handoff matter more than the lowest starting price. Its plans start at $5 per user monthly, with a $30 minimum monthly invoice for monthly plans. Choose When I Work for lower-cost scheduling and messaging: Essentials starts at $2.50 per user monthly and includes unlimited users. It offers a 14-day trial; neither product lists a free plan. Both offer annual billing, but annual prices are not published.
01Side by side
| Deputy | When I Work | |
|---|---|---|
| Starting price | $5/user/month | $2.50/user/month |
| Free plan | No free plan listed | No free plan listed |
| Best for | Scheduling through compliance, HR and payroll | Hourly teams needing scheduling and messaging |
| Core strength | Labor compliance and workforce management | Scheduling, time tracking and team messaging |
| Learning curve | Not published | Not published |
| Integrations/data | One-click approved-timesheet handoff to Paycor | API keys and webhooks on Premium |
| Team/seat costs | $30 monthly minimum; supervisors count as users | Essentials includes unlimited users |
| Support | 24/7 live chat on Pro | Support terms not published |
Deputy Choose Deputy if
- Choose Deputy if labor-law compliance tools are a priority.
- Choose Deputy if you want HR features alongside scheduling.
- Choose Deputy if you need the listed Paycor timesheet handoff.
When I Work Choose When I Work if
- Choose When I Work if the lower starting price matters most.
- Choose When I Work if you need a 14-day trial.
- Choose When I Work if Essentials' unlimited users suit your team.
02Pricing compared
Deputy starts at $5 per user/month for Lite; Core is $6.50 and Pro is $9. Monthly Lite, Core and Pro invoices have a $30 minimum. Deputy says annual billing saves 10%, but its annual prices are not published. Payroll is an add-on at $8 per user/month plus a $49 monthly base fee, and is available on annual Core and Pro plans in the US. HR is another add-on at $2 per user/month.
When I Work starts lower: Essentials is $2.50 per user/month, Pro is $5 and Premium is $8. Essentials lists unlimited users, but its price is still per user. Annual prices are not published. Time Tracking & Attendance is an add-on with no published price. When I Work offers a 14-day trial; neither product lists a free plan. Choose based on the full bill, not just the entry price.
03Features and depth
Deputy covers scheduling, timekeeping, labor compliance, HR and payroll workflows. Lite includes basic scheduling and timesheets, time clocking, leave and availability management, and labor law compliance. Core adds auto-scheduling, demand forecasting, timesheet auto-approval, and wage and labor budgets. Pro adds SSO, a sandbox, and 24/7 live chat. Deputy also says approved timesheets can be sent to Paycor in one click; payroll itself is a paid add-on in the US.
When I Work focuses on hourly-team scheduling, time tracking and messaging. Essentials includes auto-scheduling, multi-week and multi-location schedules, templates, and team messaging. Pro adds scheduling rules, role permissions, custom reporting and time-zone switching; Premium adds API keys, webhooks and SAML/SSO. Its product details also list GPS clock-ins, geofencing, shift swaps and labor forecasting, but Time Tracking & Attendance is a separately priced add-on with no published price. Deputy is the broader fit when HR and compliance matter; When I Work makes a clearer case for scheduling and team communication at a lower starting price.
04Ease of use and learning curve
Our review scores give When I Work the edge for ease of use: 6.5 versus Deputy’s 5.5. That is a modest difference, not proof that every team will find it simpler. When I Work’s listed Essentials tools center on scheduling and messaging. Deputy’s plans span scheduling, timekeeping and compliance, with HR and payroll available as add-ons, so teams choosing those tools will have more areas to set up.
Neither product’s pricing details establish how long onboarding takes. We’d compare the workflows your team needs and confirm add-on costs before switching, rather than treating the lower entry price as the whole decision.
Questions people ask
Which is cheaper, Deputy or When I Work?
When I Work has the lower listed starting price: Essentials is $2.50 per user/month, compared with Deputy Lite at $5. Deputy’s monthly plans also have a $30 minimum invoice. Add-on costs can change the comparison: When I Work does not publish its time-tracking add-on price.
Is When I Work a good app for shift scheduling?
Its listed features include schedule templates, multi-week and multi-location scheduling, auto-scheduling, shift changes and team messaging. Essentials starts at $2.50 per user/month and includes unlimited users, according to the plan details. Whether it fits depends on whether your team also needs tools such as HR or labor compliance.
Does Deputy include payroll?
Deputy lists payroll as an add-on, not as part of the base plan. In the US, it costs $8 per user/month plus a $49 monthly base fee and is available on annual Core and Pro plans. Deputy says approved timesheets can be sent to Paycor in one click.
Which product offers a free trial?
When I Work lists a 14-day free trial. Neither Deputy nor When I Work lists a free plan. Deputy’s HR add-on is free for 30 days, according to its pricing details, but that is an add-on promotion rather than a free version of the full product.