When I Work pricing: Essentials at $2.50 per user, Pro at $5, Premium at $8, per-team cost math, and where it fits against competitors

Name: When I Work
Brand: When I Work
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How much does When I Work cost?

When I Work costs $2.50, $5 or $8 per user per month on the Essentials, Pro and Premium plans. Time tracking is an add-on at $1.50 per user on Essentials or $2 per user on Pro and Premium. Billing is monthly or annual, and there is no free plan.

Prices verified Sep 2026. Sources: When I Work pricing page, OnTheClock: When I Work review (Feb 2026), add-on prices.

When I Work pricing is simple on the surface: $2.50, $5 or $8 per user per month for the Essentials, Pro and Premium plans. There are no per-location charges. The catch is that time tracking is a paid add-on on every plan, at $1.50 or $2 per user. A 14-day free trial requires no credit card. For small businesses evaluating scheduling tools, the $2.50 entry point makes When I Work one of the cheapest purpose-built scheduling options on the market.

This pricing breakdown covers what each plan includes, what the time tracking add-on adds to the bill, where per-user pricing works and where it loses ground at scale, how When I Work compares to Deputy, Homebase and 7shifts on price, and how to use the 14-day trial to choose a plan.

Written by Maya PatelFact-checked by ChandrasmitaReviewed Jun 11, 2026Last updated Sep 25, 2026

Use this When I Work pricing page to understand what buyers actually pay, what changes the cost, and what to verify before procurement.

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Trial: 14-day free trial, no credit card.

When I Work pricing overview: what the published plans cost and the per-team math

At $2.50 per user per month, When I Work Essentials is among the cheapest paid scheduling platforms available. A 30-person restaurant pays $75 per month for a purpose-built scheduling tool with a well-rated mobile app, and a 50-person retail operation pays $125. Few competitors match this for scheduling alone: Deputy's cheapest plan is $5 per user billed annually, Homebase's paid plans start at $24 per location billed annually, and Connecteam starts at $29 per month for up to 30 users billed annually.

Time tracking is the main upgrade trigger, and it is an add-on rather than a plan. If you need employees to clock in and out through When I Work, add $1.50 per user on Essentials or $2 per user on Pro and Premium. That makes Essentials with time tracking $4 per user and Pro with time tracking $7 per user. At $7, Pro costs more than Deputy Core at $6.50 per user billed annually, which includes time clocking and auto-scheduling. Past that point you are paying for When I Work's clean interface and mobile app rather than feature depth.

The per-user pricing scales linearly with no published volume discounts. A 200-person team on Pro with time tracking pays $1,400 per month. At that scale, platforms with more capabilities come into range: Deputy Core costs $1,300 per month for 200 users billed annually, and Homebase All-in-One costs $120 per location per month on monthly billing, which can be much cheaper for businesses with large teams per site. When I Work's price advantage erodes as team size grows. The sweet spot is 10 to 75 employees.

There are no per-location fees, which helps multi-location businesses. A 5-location restaurant group with 15 employees per location pays $4 x 75 = $300 per month on Essentials with time tracking, or $525 on Pro with time tracking. Homebase paid plans for 5 locations cost $150 to $600 per month on monthly billing ($120 to $480 billed annually). The per-user model favors businesses with fewer employees per location; the per-location model favors businesses with many employees per location.

When I Work plans and prices, verified Sep 2026
Plan	Price	Billing unit	What's included
Essentials	$2.50 per user/mo	per user per month	Auto scheduling, multi-week and multi-location scheduling, team messaging and integrations.
Pro	$5 per user/mo	per user per month	Adds advanced scheduling, scheduling rules, custom reporting and role permissions.
Premium	$8 per user/mo	per user per month	Adds API key access, webhooks and SAML/SSO.
Time & attendance add-on	+$1.50 per user/mo (Essentials); +$2 per user/mo (Pro, Premium)	per user per month	Clock-in and out, timesheets and attendance tracking.
Enterprise	Custom quote	per contract	Workforce management pricing for large organizations.

What When I Work costs for 10, 50 and 200 employees

When I Work estimated monthly cost by company size
Plan	10 employees	50 employees	200 employees
Essentials	$25/mo	$125/mo	$500/mo
Pro	$50/mo	$250/mo	$1,000/mo
Premium	$80/mo	$400/mo	$1,600/mo

Monthly cost in USD before tax, add-ons and implementation fees. “n/a” means the plan does not serve that headcount or the vendor does not publish a figure for it.

Prices verified Sep 2026. Sources: When I Work pricing page, OnTheClock: When I Work review (Feb 2026), add-on prices.

How to evaluate When I Work pricing before you talk to sales

When I Work pricing should be evaluated in the context of team size, operating complexity, and the commercial metric that makes cost rise over time.

Buyers should use this page to understand more than the headline price. The real decision usually depends on implementation scope, support level, add-on exposure, and whether the pricing model still makes sense once the team grows.

Clarify whether cost scales by employee count, recruiter seats, payroll runs, locations, or another metric.
Confirm what implementation, premium support, compliance, or service add-ons do to total spend.
Model pricing against the actual team size and operating complexity expected over the next 12 months.

When I Work plan breakdown: Essentials at $2.50 vs Pro at $5 vs Premium at $8

Start the 14-day trial with the time tracking add-on switched on, even if you think scheduling alone is enough. Testing the time clock costs nothing during the trial and helps you decide whether the add-on is worth $1.50 to $2 per user. If your POS system or an existing tool already handles clock-in well, leave the add-on off when you buy.

Choose Essentials if you need solid scheduling and messaging at the lowest price. Choose Pro if you need scheduling rules, role permissions or custom reports. Choose Premium only if you need API access, webhooks or SSO. Add time tracking to any plan if you want scheduling and clock-in in one platform.

When I Work Essentials — scheduling at $2.50/user/month

Essentials includes the core scheduling workflow: auto scheduling, multi-week and multi-location schedules, shift swapping, open shifts, availability and time-off requests, templates and team messaging, plus integrations. It does not include time tracking unless you add it for $1.50 per user. At $2.50 per user, a 50-person team pays $125 per month for a clean, purpose-built scheduling tool that employees actually use, or $200 with time tracking. This is the plan for businesses that mainly need schedule management.

When I Work Pro and Premium — $5 and $8 per user/month, plus the time tracking add-on

Pro at $5 per user adds advanced scheduling, scheduling rules, custom reporting and role permissions. Premium at $8 per user adds API key access, webhooks and SAML/SSO. Time tracking and attendance (clock-in, timesheets, attendance reports) cost another $2 per user on either plan. A 50-person team pays $350 per month on Pro with time tracking, or $500 on Premium with time tracking. Most small businesses will not need Premium unless IT requires SSO.

When I Work cost considerations: linear scaling, missing features, and total solution math

Linear per-user scaling with no volume discounts makes When I Work expensive at 150+ employees

The per-user pricing is simple but unforgiving at scale, and the time tracking add-on is easy to miss. A 200-person team on Pro with time tracking pays $1,400 per month with no volume breaks. At that level, Deputy Core ($1,300 per month for 200 users billed annually, time clock included) and Homebase (per-location pricing with unlimited employees) become competitive or cheaper while offering more capability. Model your cost at 12 and 24 months, since pricing that works at 30 employees may not work at 150.

No break compliance creates risk for businesses in regulated states

When I Work does not track or enforce meal and rest break requirements the way dedicated compliance tools do. For businesses in California, Oregon, Washington and other jurisdictions with complex break laws, this gap creates compliance exposure. The savings from a lower per-user price can be wiped out by a single break compliance violation. Deputy includes labor law compliance tools on its $5 Lite plan and advanced compliance on the $6.50 Core plan (annual rates). Factor compliance risk into your total cost comparison.

Adding separate tools for payroll, HR, and hiring increases total stack cost

When I Work is exclusively scheduling and time tracking. If you need payroll, HR, hiring, or training capabilities, you are buying additional tools — Gusto for payroll, BambooHR for HR, etc. The combined monthly cost of When I Work plus separate tools may exceed what Homebase or Connecteam charge for an all-in-one platform. Calculate your total tool stack cost, not just the scheduling tool cost.

How When I Work pricing compares to Deputy, Homebase, and 7shifts

When I Work vs Deputy on pricing and feature depth

When I Work Essentials at $2.50 per user is cheaper than Deputy Lite at $5 per user billed annually. Once you add time tracking, When I Work Pro costs $7 per user versus $6.50 for Deputy Core, which includes auto-scheduling, demand forecasting, labor budgets and advanced compliance. When I Work offers a simpler interface and a well-liked mobile app. For businesses that need operational depth, Deputy delivers more for the money. For businesses that value simplicity, When I Work's interface may be worth the trade-off.

When I Work vs Homebase on pricing models

When I Work charges per user ($2.50, $5 or $8, plus time tracking). Homebase charges per location (free Basic for up to 10 employees, then $30 to $120 per location per month, or $24 to $96 billed annually). For a 50-person team at 2 locations, When I Work Pro with time tracking costs $350 per month while Homebase Essentials costs $60 per month ($48 billed annually). Homebase is much cheaper for businesses with many employees per location, and its free plan covers basic scheduling and time tracking for very small teams. When I Work wins on scheduling interface and mobile app.

When I Work vs 7shifts for restaurants

7shifts is built for restaurants, with tip management, labor compliance and POS integration. Its paid plans start at $39.99 per location per month billed annually ($44.99 monthly) for Essentials. For a single-location restaurant with 30 employees, When I Work Essentials with time tracking costs $120 per month and Pro with time tracking $210, versus $39.99 for 7shifts Essentials. 7shifts is much cheaper per location and includes restaurant-specific features, so for food service businesses it is usually the better value.

When I Work pricing buyer checklist: choosing a plan, time tracking and trial strategy

Start the 14-day trial with time tracking on to test scheduling and the time clock together

The trial includes full access. Switch on the time tracking add-on so you can evaluate the whole platform. If you decide the time clock is unnecessary, leave the add-on off when you buy. You cannot evaluate what you have not tried.

Compare total solution cost, not just scheduling tool cost

If you need When I Work plus Gusto for payroll plus BambooHR for HR, add up all subscriptions. Compare the total against Homebase, which includes scheduling, time tracking, hiring, HR basics, and optional payroll in one platform.

Test shift swapping with real employees during the trial

Have at least two employees swap a shift during the trial to verify the workflow matches your approval preferences. Shift swapping is one of When I Work's most valued features — validate it works for your team.

Check break compliance requirements for your operating states

If you operate in California, Oregon, Washington, or NYC, When I Work's lack of break tracking creates compliance risk. Verify whether this gap is acceptable or whether you need Deputy's break compliance tools.

Model the per-user cost at your projected team size in 12 months

The pricing that is affordable at 30 employees may be expensive at 100+. Calculate your projected cost and compare against per-location alternatives that become more economical at larger team sizes.

Frequently asked questions about When I Work pricing

When I Work pricing is simple and among the most affordable in the scheduling category. Essentials at $2.50 per user is hard to beat for businesses that only need scheduling. Once you add time tracking ($1.50 to $2 per user), Pro at $7 per user all-in costs more than Deputy Core, which offers more depth. The platform's value is strongest for teams of 10 to 75 hourly workers where simplicity, mobile app quality and low cost matter most. Above 100 employees, linear pricing and thinner compliance and labor analytics make When I Work less competitive against platforms that offer more per dollar.

Frequently asked questions

How much does When I Work cost for a 50-person team?

For 50 users, Essentials costs $125 per month ($2.50 x 50), Pro $250 ($5 x 50) and Premium $400 ($8 x 50). Time tracking is an add-on: $1.50 per user on Essentials and $2 per user on Pro and Premium, which brings the totals to $200, $350 and $500. All plans are billed per user with no per-location charges. A 14-day free trial is available with no credit card required.

Does When I Work have a free plan?

No. When I Work does not offer a free plan. Essentials starts at $2.50 per user per month, Pro at $5 and Premium at $8. A 14-day free trial is available. For free scheduling, Homebase offers a Basic plan at no cost with scheduling and time tracking for one location with up to 10 employees.

What is the difference between When I Work Essentials, Pro and Premium?

Essentials ($2.50 per user) includes auto scheduling, multi-week and multi-location scheduling, team messaging and integrations. Pro ($5 per user) adds advanced scheduling, scheduling rules, custom reporting and role permissions. Premium ($8 per user) adds API access, webhooks and SAML/SSO. Time tracking and attendance are not included in any plan; they cost an extra $1.50 per user on Essentials or $2 per user on Pro and Premium.

Is When I Work cheaper than Deputy?

When I Work Essentials at $2.50 per user is cheaper than Deputy's cheapest plan, Lite, at $5 per user billed annually. With time tracking added, Essentials is $4 per user and Pro is $7 per user, which puts Pro above Deputy Core at $6.50 per user billed annually. Deputy Core includes time clocking, auto-scheduling and demand forecasting in that price. When I Work is cheaper for basic scheduling; Deputy usually delivers more per dollar once you need scheduling plus time tracking.

Does When I Work offer volume discounts for large teams?

When I Work does not publish volume discounts. The per-user pricing scales linearly: a 200-person team on Pro with time tracking pays $1,400 per month with no apparent break. For large teams, per-location pricing such as Homebase ($30 to $120 per location per month, or $24 to $96 billed annually, with unlimited employees) may be cheaper depending on your employee-to-location ratio.

Is the When I Work 14-day trial enough to evaluate the platform?

Yes. The 14-day trial gives full access and is generous for a scheduling tool. Turn on the time tracking add-on during the trial so you can test scheduling and the time clock together. Build one complete weekly schedule, have employees download the mobile app, test shift swapping with two employees, and run the time clock for at least one full week. You will know within 14 days whether the platform fits your operations.

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