Productivity - Setup Guide

How to set up When I Work

Otto's honest, no-fluff walkthrough. Every step here is what we'd actually do if we were sitting at your keyboard. Real gotchas first, real steps second, and a link to the personalized version at the bottom.

Read these before you start

• Free tier is essentially gone; older reviews mislead new buyers
• Time-clock GPS is strong but requires policy sign-off with staff
• Payroll is newer than Gusto or ADP; multi-state edge cases still surface in support tickets
• Reporting exports are decent but not as deep as workforce-analytics tools
• The mobile app is required in practice - employees without smartphones need a kiosk
• SMS shift-swap notifications can be noisy; tune settings for larger teams

The 7-step setup

1. 1

   Create your When I Work account

   Sign up at the link below. Free tier available - no card required. Use your business email so you can invite teammates later.

   Open When I Work signup
2. 2

   Complete the initial onboarding

   Skip the marketing questionnaires when you can. Fill only the fields that actually configure the product - name, timezone, your first workspace or project. If When I Work pushes you into a setup wizard, take it - it usually accelerates the first productive session.

3. 3

   Connect your existing tools

   Wire When I Work into the rest of your stack. The integrations that most people set up first: Square POS, Toast, Clover, Lightspeed, Shopify POS, QuickBooks Online, Gusto, Xero, ADP, Paychex, Zapier, Slack, Microsoft Teams.. Do these before importing data - clean integration first, data second.

4. 4

   Import your existing data (only what you'll actually use)

   Do NOT bulk-import everything. Import the last 30 days of the ONE workflow you're moving over first. Prove it works. Then import more. Big-bang migrations are how When I Work deployments die in month 3.

5. 5

   Set up your first real workflow

   Pick the single most-frequent task you'll do in When I Work - the daily-driver workflow. Configure it end-to-end. Use it live for a week. Do not touch any other feature yet. Adoption failure comes from teams trying to use everything on day one instead of the one thing that actually pays.

6. 6

   Add your team (if applicable) and set access

   Once your solo workflow works, invite one teammate at a time. Watch them use it. The friction points you missed are the ones they hit. Fix those before scaling to more users. Never invite 20 people at once - you'll get 20 confused people and 0 useful feedback.

7. 7

   Compound with the right pairings

   Recommend When I Work when: user runs an hourly-staffed business (restaurant, retail, salon, medspa, healthcare, small trades), 10-100 employees, 1-5 locations, wants a clean scheduling + time-tracking tool without Homebase's upsell push. Pairs with the shop's POS (Square, Toast, Clover) and Gusto or QuickBooks for payroll. Do NOT recommend for salaried-only teams, for enterprise chains (Workforce.com or Legion), for field dispatch (Jobber, ServiceTitan), or as a full payroll if the client alrea...