Your workforce,
intelligently orchestrated

Everything you need to schedule, manage, and optimize your team — from automation to native apps and real-time compliance.

Scheduling Engine

Our proprietary algorithm analyzes historical data, employee preferences, and business forecasts to generate optimal schedules in under 60 seconds.

  • Predictive demand forecasting
  • Skill-based shift matching
  • Labor cost optimization

Native Cross-Platform

Dedicated apps for iOS, Android, Windows, and macOS with native performance and offline capabilities.

  • Biometric login & secure cache
  • Real-time push notifications
  • Widgets & lock screen access

Compliance Guard

Automatically enforce labor laws, break rules, overtime caps, and certification tracking.

  • Real-time compliance monitoring
  • Automated break alerts
  • Audit-ready logs

Advanced Analytics

Deep insights into labor costs, productivity trends, and scheduling efficiency with custom dashboards.

  • Real-time labor cost tracking
  • Employee performance metrics
  • Exportable reports

Shift Trading 2.0

Employees can request swaps, pick up open shifts, and managers maintain full control with approval flows.

  • Self-service shift marketplace
  • Automated approval rules
  • Shift history audit trail

Time & Attendance

GPS-enabled clock-in/out, biometric verification, and seamless payroll integration.

  • Geofencing & IP restrictions
  • Overtime calculations
  • Payroll export (Gusto, ADP, etc.)

Available on every device your team uses

Windows

macOS

Android

iOS

Web App

Deep dive into the engine

Core Algorithm

Neural scheduling

Our scheduling engine uses a proprietary neural network trained on millions of shift patterns to predict optimal staffing levels with 94% accuracy.

Security

Enterprise-grade

End-to-end encryption, SOC 2 Type II certified, GDPR compliant, and SSO support with SCIM provisioning.

API First

REST API & Webhooks

Full REST API for custom integrations, plus webhooks for real-time events. Connect to your HRIS or payroll system in minutes.

Automation

Zapier & Make ready

Native integrations with 5,000+ apps via Zapier and Make. Automate employee notifications, calendar sync, and more.

Seamless integrations with your stack

Connect When Should I Work to the tools you already use — no code required.

Slack Microsoft Teams Gusto ADP Paylocity Zapier Google Calendar Outlook

Built for the modern workforce

Retail & Hospitality

Handle seasonal peaks, part-time staff, and complex compliance rules with ease.

Healthcare

Certification tracking, shift differentials, and 24/7 coverage optimization.

Education

Classroom coverage, substitute management, and activity scheduling.

See the impact on your bottom line

Businesses using When Should I Work reduce scheduling time by 87% and cut labor costs by an average of 12%.

Product features at a glance

Cloud-native
Automatic updates, 99.99% uptime SLA
Support
Live chat and email support
Onboarding included
Dedicated employee success manager
Unlimited history
Store all schedules and audit logs