When I Work pricing: what each plan costs and what it includes
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When I Work costs $2.50 per user a month on Essentials, $5 on Pro and $8 on Premium, according to its pricing page (checked October 16, 2026). For 20 hourly staff that is $50, $100 or $160 a month.
The cheapest number may not be the one you pay. The same page conflicts on whether time tracking and multi-location scheduling need a plan above Essentials, so we budget on Pro. When I Work scores 58 out of 100.
When I Work is a per-user employee scheduling app for hourly teams, with shift swaps, a time clock and team messaging, and payroll offered through a partnership with Rippling.
On this page
When I Work pricing at a glance
- Per user
- $2.50 to $8a month, Essentials to Premium
- 20 staff on Pro
- $100 a month20 x $5
- Payroll
- Via RipplingRippling quotes only
- Our score
- 58/100scheduling category
We score on published prices and terms, not hands-on testing. The method is on our scoring page.
When I Work plans and what 10 or 20 staff cost
| Plan | Price | 10 users | 20 users |
|---|---|---|---|
| Essentials | $2.50 per user a month | 10 x $2.50 = $25 | 20 x $2.50 = $50 |
| Pro | $5 per user a month | 10 x $5 = $50 | 20 x $5 = $100 |
| Premium | $8 per user a month | 10 x $8 = $80 | 20 x $8 = $160 |
| Enterprise | Custom | Quote | Quote |
Source: When I Work pricing page (wheniwork.com/pricing), checked October 16, 2026. 14-day trial, no card. Cards only. The page conflicts on whether time tracking and multi-location need a plan above Essentials.
At $2.50 a user, Essentials is the lowest per-user price among the five apps we rank. Deputy's lowest tier is twice that at $5. The question is whether Essentials does what you need.
The time tracking conflict on the pricing page
When I Work's pricing page conflicts on whether time tracking, and multi-location scheduling, need a plan higher than Essentials. If you need staff to clock in, assume Pro at $5 per user until When I Work confirms otherwise in writing.
For a 20-person team the gap is $50 a month ($600 a year): $50 on Essentials against $100 on Pro. That is why our price score uses Pro, and why When I Work gets 20 of 30 price points rather than the 25 that Essentials at $50 would earn. Start the 14-day trial on the plan you intend to buy and test clock-in before entering a card.
Payroll through Rippling
When I Work does not run its own payroll. Payroll comes through a partnership with Rippling, which does not publish prices: its FAQ says plans "start at $8 per employee per month, with a monthly base fee" but names neither the product nor the base fee (Rippling pricing page, checked October 16, 2026). Read what Rippling actually costs before you plan on it.
If you want a known payroll bill, the published alternatives for 10 people are Square Payroll at $95 a month and Gusto Simple at $109. Our research does not document whether When I Work connects to those two, so check before signing. For payroll and scheduling from one vendor at a published price, Homebase charges $49 + $6 per employee paid.
Features: swaps, messaging and the clock
When I Work documents shift scheduling, shift swaps, a time clock and team messaging. Auto-scheduling, labor law compliance tools, GPS or geofenced clock-in and tip pooling are not documented on the pages we checked. Restaurants that need tip pooling should compare restaurant scheduling apps.
Contract, billing and support
- Contract: monthly or annual; the FAQ promises "no contracts or hidden fees". Annual terms are not detailed and no refund rule is published.
- Cancel: cancel anytime.
- Payment: cards only.
- Support: Help Center, live chat and a ticket form. Phone support and hours are not published.
When I Work reviews
When I Work has 4.4 out of 5 from 411 reviews on G2 and 3.8 out of 5 from only 6 reviews on Trustpilot (both seen October 16, 2026). Six reviews is too few to read anything into, and our scoring caps the complaint score when a vendor has fewer than 20 reviews.
How we score When I Work
| Criterion | Points | Why |
|---|---|---|
| Price for 20 hourly staff | 20 of 30 | Essentials is $2.50 per user, but the page conflicts on whether time tracking needs a higher plan, so we price Pro at $5 x 20 = $100 a month (20). |
| Scheduling and time clock features | 15 of 25 | Shift scheduling, a time clock, and shift swaps with team messaging are documented (5 each); auto-scheduling and labor law compliance tools are not published on the pages we checked (0). |
| Payroll integration | 7 of 15 | Payroll runs through a Rippling partnership (7). |
| Contract terms | 11 of 15 | Cancel anytime, with 'no contracts or hidden fees' in the FAQ (5); annual terms are not detailed and no refund rule is published (3); no billing traps documented, terms not fully read (3). |
| Documented complaint patterns | 5 of 15 | Trustpilot 3.8 from only 6 reviews (1 of 4); complaint patterns were not researched this pass (default 2 of 6), so 3 of 10 scales to 5 of 15. |
| Total | 58 of 100 | Best for hourly teams that want low per-user scheduling cost. |
Source: HRPricing.com scheduling scores, checked October 17, 2026. Scores use published terms and prices, not hands-on testing.
Who When I Work fits
What works
- Lowest per-user price of the five ($2.50).
- Shift swaps and messaging documented.
- Cancel anytime, no contracts per the FAQ.
Watch out for
- Pricing page conflicts on time tracking and multi-location.
- No payroll of its own; Rippling quotes only.
- No phone support published.
Bottom line: When I Work suits teams that only need a schedule and shift swaps, where Essentials at $2.50 a user is cheap. Once you need the clock, Connecteam's flat $35 for up to 30 users is cheaper for 20 staff than Pro at $100, though it has no payroll of its own. Homebase's built-in payroll gives a published all-in price ($199 for 20 staff at one location). See the full scheduling software comparison, and budget wages with our employer cost calculator and state minimum wages for 2026.
Frequently asked questions
How much does When I Work cost?
Does When I Work Essentials include time tracking?
Does When I Work do payroll?
Is there a When I Work free trial?
Can I cancel When I Work anytime?
Sources (6)
- When I Work: When I Work pricing page (checked Oct 16, 2026)
- G2: When I Work reviews (4.4, 411 reviews) (seen Oct 16, 2026)
- Trustpilot: When I Work reviews (3.8, 6 reviews) (seen Oct 16, 2026)
- Rippling: Rippling pricing page (checked Oct 16, 2026)
- Gusto: Gusto pricing page (checked Oct 16, 2026)
- Square: Square Payroll pricing (checked Oct 16, 2026)
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