When I Work Pricing 2026: Essentials, Pro, Premium Per User

When I Work costs $2.50 per user a month on Essentials, $5 on Pro and $8 on Premium, according to its pricing page read on 18 October 2026. Each plan card carries a "Time Tracking & Attendance" switch, and turning it on raises the rates to $4, $7 and $10. There is no free plan, only a 14-day trial with no card required, and Enterprise is priced by quote.

That headline rate is real, but it is the scheduling-only price. A shift team that wants staff to clock in from their phones, round punches for payroll and export timesheets pays the higher figure, which is 60% more on Essentials. This page works through which number applies to you, what a 10, 25, 50 or 100 person crew pays, and how the bill compares with Deputy, Sling and Homebase. For the product verdict, our When I Work review covers features and fit.

Toolradar data: When I Work's entry tier ranks joint #2 of 16 team chat tools with verified per-user pricing in the October 2026 snapshot on its Toolradar profile, against a peer median of $5.50 per user a month. Toolradar is the software directory we run, and in plain terms the figure means the base rate sits near the bottom of the per-seat market.

What does each When I Work plan cost?

When I Work sells three self-serve plans, all priced per user per month, with unlimited users on every tier. The table shows both prices the page can display for each plan, depending on the attendance switch.

Prices were read on When I Work's pricing page on 18 October 2026, before tax. The page prints no annual price for any plan, although its FAQ says both monthly and annual billing are available, so any annual saving is something you ask sales for rather than read off the page.

The step from Essentials to Pro doubles the per-user rate. What it buys is control: scheduling rules that flag conflicts, custom permissions for managers and supervisors, and the ability to share staff between sites. A single cafe rarely needs any of that, while a three-store retailer that moves people between locations every week probably does.

Premium is an integration tier. The $3 a head over Pro pays for API access, webhooks and SSO sign-in. If your IT team does not plan to connect the rota to another system or enforce company logins, Premium adds cost without changing how managers schedule.

What does the Time Tracking & Attendance switch add?

The switch adds $1.50 per user a month on Essentials and $2 on Pro and Premium. It is off by default, which is why the headline price is the lower one and why a quick look at the page understates the bill for most shift teams. The plan comparison table on the same page groups the time clock features under that switch and greys them out while it is off.

Here is what the switch covers, per that comparison table:

• Geofencing and early clock-in prevention to stop time theft
• Photo capture at clock in and clock out
• Punch data to the exact second, with reminders for staff who forget to clock in or out
• Timesheet export to Excel, rounding rules to match payroll, and automatic break deductions
• Payroll integrations with partners such as Gusto and ADP

The pricing FAQ tells a different story. It says every plan includes "employee scheduling, time and attendance software, and team messaging", and that the trial includes the time clock. The plan cards and the FAQ cannot both be the full picture, so ask sales in writing which rate covers clocking in before you sign. For a 30-person crew the gap is $45 a month on Essentials, or $540 over a year.

Our reading: if staff clock in through When I Work and timesheets flow into payroll from it, budget the higher figure. If clocking happens in your POS or payroll tool and When I Work only builds the rota, the lower rate may hold.

Which rate applies to a multi-location business?

The pricing FAQ says When I Work starts at the entry rate "for single-location teams, and $5 per user per month for multi-location businesses." Yet the Essentials card lists multi-location scheduling as an included feature. That leaves two readings for a business with more than one site.

The cautious one is that a second location moves every user to the Pro-level rate. On that reading, a 20-person team across two stores pays $100 a month, not $50, before the time clock switch. With the switch on Pro, the same team pays $140.

Labor sharing, the feature that lets one employee pick up shifts at another store, sits in Pro on the comparison table. So a multi-site operator who wants to move staff between locations ends up on Pro either way. Settle the question with sales, then plan on the Pro column if you share staff.

What does When I Work cost for your team size?

The table below multiplies the published rates by common shift-team sizes. Every total is our arithmetic on When I Work's list prices, not a vendor quote, and assumes monthly billing with every person who logs in counted as a user.

Two patterns stand out. First, the time clock switch is the cheaper upgrade: 25 users pay $37.50 extra a month for clocking on Essentials, against $62.50 extra to move to Pro without it. Second, Premium with the switch on is four times the Essentials headline, so a 100-person operation that wants SSO is looking at $12,000 a year, not $3,000.

Count managers and owners in the user total too: the plans are priced per user, so anyone who logs in to build or approve the schedule needs a seat, even if they never work a shift.

How does When I Work compare on cost?

When I Work's base rate is among the lowest per-user prices for a paid scheduler, but two rivals beat it for specific team shapes. Here is a 25-person, single-location team on each vendor's entry paid plan, priced from each vendor's own page on 18 October 2026:

Rates come from Deputy's pricing page, Sling's pricing page and Homebase's pricing page. Each plan bundles different features, so compare what is included before reading the totals as like for like.

Deputy costs about twice as much per head but its Lite plan is sold as scheduling plus time tracking in one rate, and its monthly plans carry a $30 minimum per invoice. Our Deputy pricing breakdown covers that minimum and the add-ons.

Sling is cheaper on paper and has a free plan for up to 30 users. For a small team that only needs a rota, it is the price floor, as the best free employee scheduling apps guide shows.

Homebase wins for one busy location. Its Essentials plan bills per site, so 25 people cost the same as 5. Past 12 users on a single site, When I Work's Essentials rate overtakes Homebase's flat fee, which is the trade our Homebase vs When I Work comparison works through, and our Homebase pricing guide lists every Homebase tier.

Where When I Work wins is the multi-site business with few people at each site, where per-location pricing punishes every small branch. The best shift scheduling software ranking and our Homebase vs Deputy comparison cover the other options at the same headcount.

Hidden costs and gotchas

• The headline rate excludes the time clock switch. Clocking, rounding and timesheet exports add $1.50 to $2 per user a month on the plan cards.
• No published annual price. The page offers annual billing but prints no annual figure, so there is no list discount to count on.
• Multi-site may mean the Pro-level rate. The FAQ ties multi-location businesses to the Pro-level price even though Essentials lists multi-location scheduling.
• No free plan. After the 14-day trial the account needs a paid plan.
• Payroll is an integration, not a product. When I Work connects to payroll tools rather than running payroll itself. The pricing page promotes Rippling as its preferred partner, with the first six months of Rippling free for When I Work customers; budget for Rippling after that, as our Rippling review explains.

How we priced this

We read When I Work's pricing page on 18 October 2026: the plan cards in both switch positions, the plan comparison table and the pricing FAQ. Rival prices were read the same day on each vendor's own pricing page, linked above. Totals are our arithmetic on list rates before tax, and HRpresso holds no When I Work contract, so no figure is a negotiated quote. More cost comparisons across clock-in tools sit in our time clock apps pricing comparison and the best time clock software guide.

FAQ

How much does When I Work cost per month?

When I Work costs $2.50 per user a month on Essentials, $5 on Pro and $8 on Premium, per its pricing page read on 18 October 2026. Turning on the Time Tracking & Attendance switch raises those rates to $4, $7 and $10. Enterprise pricing is a custom quote.

Does When I Work have a free plan?

No. When I Work offers a 14-day free trial with full access and no credit card, but no permanent free tier. Sling's free plan covers up to 30 users and Homebase's Basic plan is free for one location with up to 10 employees, so both are cheaper starting points for a rota alone.

Is time tracking included in When I Work's price?

It depends on which part of the page you read. The plan cards show time tracking as a switch that adds $1.50 per user on Essentials and $2 on Pro and Premium, while the FAQ says every plan includes time and attendance software. Get the answer from sales in writing before you budget.

How much does When I Work cost for 20 employees?

Twenty users cost $50 a month on Essentials, or $80 with the time clock switch on. On Pro the same team pays twice the Essentials bill, or $140 with the switch. Owners and managers who log in count as users, so include them in the 20.

Is When I Work cheaper than Deputy?

Yes, on list price. When I Work's entry plan costs half of Deputy Lite's annual per-user rate, and Deputy's monthly Lite rate is $5.50. With the time clock switch on, When I Work Essentials still costs less per user than Deputy Lite on either billing cycle.

Can I cancel When I Work anytime?

Yes. The pricing FAQ says you can switch plans, add or reduce seats, or cancel at any time with no contracts. That makes it easy to scale seats with seasonal hiring, though the FAQ does not say whether an annual plan is refunded on early cancellation.

Cite this: HRpresso, "When I Work Pricing 2026: Essentials, Pro, Premium Per User", October 2026.

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