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Restaurants · head to head

Square for Restaurants vs When I Work

Square for Restaurants logo

Square for Restaurants

Restaurants

Restaurant POS system that works for you

From
Free
Rated
-
Full reviewWebsite
When I Work logo

When I Work

Restaurants

Scheduling and time tracking made simple

From
$2.5/user/month
Rated
-
Full reviewWebsite

The short version

  • Only Square for Restaurants has a free tier, so it costs nothing to try first.
  • Each has a real cost: Square for Restaurants the Square KDS and Square Kiosk apps are not available on the free plan; When I Work aPI key access, webhooks and SAML single sign on require the Premium plan at $8 per user per month
  • They diverge on capability: Square for Restaurants covers Table management, When I Work covers Shift scheduling.
  • Prices and features above were last checked on 30 August 2026.

Where they differ

Only the attributes on which Square for Restaurants and When I Work actually diverge.

Attributes where Square for Restaurants and When I Work differ
AttributeSquare for RestaurantsWhen I Work
Starting priceFree$2.5/user/month
Free tierYesNo
Founded20182010

Identical on both: pricing model (subscription), platforms (Web, Ios, Android), user rating (Not yet rated), category (Restaurants).

What each one covers

Drawn from each product's published feature list. An absence here means we hold no record of it - not that the product lacks it.

Only in Square for Restaurants

  • Table management
  • Menu customization
  • Split checks
  • Offline mode
  • Real-time reporting
  • Kitchen display
  • Caviar
  • DoorDash

Only in When I Work

  • Shift scheduling
  • Time clock
  • Team messaging
  • Availability management
  • Shift swapping
  • Mobile apps
  • ADP
  • Gusto

Both cover

  • QuickBooks
  • Web support
  • Ios support
  • Android support

What people use each for

The jobs each tool is most often brought in to do.

Square for Restaurants

  • Point of Salenot When I Work
  • Order Managementnot When I Work
  • Inventory Controlnot When I Work
  • Staff Schedulingnot When I Work

When I Work

  • Scheduling hourly shift workers across locationsnot Square for Restaurants
  • Time clock and timesheet capture for payrollnot Square for Restaurants
  • Handling shift swaps, availability and time off requestsnot Square for Restaurants

Where each one falls short

Documented limitations, not opinions. Every one is a constraint you would hit in normal use.

Square for Restaurants

  • The Square KDS and Square Kiosk apps are not available on the free plan
  • KDS and Kiosk are billed per device per month on top of the plan, so cost scales with terminals rather than locations
  • Restaurants processing over $250,000 a year are moved to custom pricing rather than the published rates

When I Work

  • API key access, webhooks and SAML single sign on require the Premium plan at $8 per user per month
  • Scheduling rules, role permissions and custom reporting require the Pro plan at $5 per user per month
  • There is no free plan; the trial lasts 14 days
  • Enterprise arrangements are priced by quote with no published rate

Pricing, plan by plan

Square for Restaurants

Free
  • FreeFree
    • POS
    • Menu management
    • Basic reporting
  • Plus$60/month
    • Advanced features
    • Live sales
    • Seat management
  • PremiumFree
    • Custom pricing
    • Dedicated support

When I Work

$2.5/user/month
  • Standard$2.5/user/month
    • Scheduling
    • Messaging
  • Advanced$6/user/month
    • Time clock
    • Labor forecasting

Which should you pick?

Choose Square for Restaurants if

  • You need table management.
  • You want to start without paying.
  • You work on Web, Ios, Android.
  • You also want menu customization.
Square for Restaurants review

Choose When I Work if

  • You need shift scheduling.
  • You work on Web, Ios, Android.
  • You also want time clock.
When I Work review

Questions people ask

Is Square for Restaurants or When I Work better?
Neither clearly leads. Square for Restaurants starts at Free and When I Work at $2.5/user/month, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
Which is cheaper, Square for Restaurants or When I Work?
Square for Restaurants has a free tier; the other does not. Paid plans start at Free for Square for Restaurants and $2.5/user/month for When I Work.
Does Square for Restaurants or When I Work run on more platforms?
Both run on Web, Ios, Android, so platform support will not decide this one for you.
Can I use Square for Restaurants for free?
Yes. Square for Restaurants has a free tier, so you can try it without paying. When I Work starts at $2.5/user/month.
What is Square for Restaurants best used for?
Square for Restaurants is most often used for point of sale, order management, inventory control, staff scheduling. Of those, point of sale and order management are not what When I Work is typically brought in for.
What can Square for Restaurants do that When I Work cannot?
Square for Restaurants covers Table management, Menu customization, Split checks, Offline mode. When I Work covers Shift scheduling, Time clock, Team messaging, Availability management. Both handle QuickBooks, Web support, Ios support, Android support.

Answered from the vendors’ own pages

Square for Restaurants: What are Square's main pricing plans for restaurants?

Square offers a free tier and Square Plus. The Free plan has $0 cost with standard processing fees. Square Plus is described as the best value tier and includes lower card processing rates than the free plan.

Source
When I Work: What is the pricing structure?

Plans start at $2.50 per user per month, billed in user tiers of five, with pricing that scales flexibly with team size.

Source
Square for Restaurants: Does Square have locked-in contracts or can I cancel anytime?

Square explicitly states no hidden fees or locked-in contracts. Customers can cancel or switch anytime. The pay-as-you-go model means you only pay when you take a payment.

Source
When I Work: Are there long-term contracts required?

No long-term contracts, no hidden surprises, and no enterprise-only paywalls. The platform scales as your business grows without binding agreements.

Source
Square for Restaurants: Does Square Plus include a free trial period?

Yes, Square Plus offers a free trial, though the specific trial duration is not clearly displayed on the pricing page.

Source
When I Work: Is there a free trial available?

Try When I Work free for 14 days with full access to all core features. No credit card is required for the trial period.

Source
Square for Restaurants: What features does Square Plus add compared to the free plan?

Square Plus includes all free plan features plus advanced POS tools, a loyalty program, email and text marketing (500 free texts, then 3 cents per text), and staff management tools.

Source
When I Work: Can I adjust or cancel my plan anytime?

You can upgrade, downgrade, or cancel at any time and adjust your plan at any time or use hibernation options during seasonal downtime.

Source
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