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Restaurants · head to head

Upserve vs When I Work

Upserve logo

Upserve

Restaurants

Restaurant management platform with insights

From
$59/month
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

  • Each has a real cost: Upserve offline terminals can only store credit card payment data for 48 hours before requiring internet connection; 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: Upserve covers Cloud POS, 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 Upserve and When I Work actually diverge.

Attributes where Upserve and When I Work differ
AttributeUpserveWhen I Work
Starting price$59/month$2.5/user/month
Pricing modelUnknownsubscription
PlatformsWeb, iPad, Android, Custom POS terminalsWeb, Ios, Android
Founded20132010

Identical on both: free tier (No), 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 Upserve

  • Cloud POS
  • Guest insights
  • Menu intelligence
  • Server performance
  • Reputation management
  • Inventory tracking
  • Xero
  • 7shifts

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.

Upserve

  • 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 Upserve
  • Time clock and timesheet capture for payrollnot Upserve
  • Handling shift swaps, availability and time off requestsnot Upserve

Where each one falls short

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

Upserve

  • Offline terminals can only store credit card payment data for 48 hours before requiring internet connection
  • Customers cannot add tips when the system operates in offline mode
  • $400 monthly penalty for using alternative payment processors instead of Lightspeed
  • No global ability to change menu items across all locations at once, requiring per-location updates
  • Mandatory 2.6% + $0.10 per transaction payment processing fee with Lightspeed

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

Upserve

$59/month
  • Core$59/month
    • Cloud-based point of sale
    • Basic reporting
    • Guest insights
  • Pro$199/month
    • All Core features
    • Inventory management
    • Online ordering

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 Upserve if

  • You need cloud pos.
  • You work on Web, iPad, Android, Custom POS terminals.
  • You also want guest insights.
Upserve 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 Upserve or When I Work better?
Neither clearly leads. Upserve starts at $59/month 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, Upserve or When I Work?
Upserve starts at $59/month and When I Work at $2.5/user/month.
Does Upserve or When I Work run on more platforms?
Upserve runs on Web, iPad, Android, Custom POS terminals. When I Work runs on Web, Ios, Android.
What is Upserve best used for?
Upserve 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 Upserve do that When I Work cannot?
Upserve covers Cloud POS, Guest insights, Menu intelligence, Server performance. 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

Upserve: Does Upserve support offline mode?

Yes. Upserve is a hybrid cloud-based system where reporting data is stored in the cloud but offline mode allows the software to store important data locally on your device in case the internet goes down, allowing transactions to continue.

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
Upserve: What is Upserve's pricing structure?

Upserve offers three plans: Core at $59/month, Pro at $199/month with advanced features like inventory management and loyalty programs, and Pro+ with custom pricing for enterprise customers. Hardware is sold separately.

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
Upserve: Does Upserve offer a free trial?

Yes, Upserve offers a 14-day free trial for new users to test the platform before committing to a paid plan.

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
Upserve: What delivery platforms does Upserve integrate with?

Upserve integrates with DoorDash, Uber Eats, and Grubhub through partner middleware services like Chowly and Deliverect, which provide real-time menu syncing and order management.

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
Upserve: What are the payment processing requirements?

Upserve requires using Lightspeed payment processing at 2.6% + $0.10 per transaction. Using alternative payment processors incurs a $400 monthly fee, making Lightspeed the mandatory choice for most restaurants.

Source
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