Pebb vs When I Work: Which Employee App Fits 11–80 Person Teams?

When I Work is a real scheduling product for hourly shops. Build the roster, open shifts, swap, message the crew about the week, and — if you turn time tracking on — punch with GPS or geofencing. Strong for “who works when.”

Pebb is an all-in-one employee app for the floor and the office. You pay per person. Basic is $2.50 per user per month for chat, shifts, clock-in, timesheets, and a directory. Premium is $4 and adds calls, a news feed, PTO, tasks, forms, a wiki, analytics, and SSO. Unlimited Spaces on both plans — a second site is another Space, not another product. Chat is org-wide. No free plan. Full trial, no card. No payroll, LMS, or ATS. GPS is a stamp on clock-in (optional near-branch), not live breadcrumbs. We are not pivoting to “engagement.” This is the daily employee app.

For 11–80 person construction, field, security, warehouse, hospitality, and multi-location teams that outgrew scheduler-plus-WhatsApp. Keep When I Work if scheduling depth, labor forecasting, and payroll/POS export are why you opened the app. This page is for everyone using it as a blunt “employee app.”

Start full trial — no card · Pebb pricing

At a glance

Pick Pebb if you want chat, shifts, GPS clock-in, timesheets, and (on Premium) calls, PTO, tasks, forms, and a wiki billed per person. Spaces unlimited. Chat org-wide. Full trial, no card. No payroll, LMS, ATS, or live GPS breadcrumbs. Offline does not fully work.

Pick When I Work if the hard problem is schedule construction — auto-scheduling, OpenShifts, labor forecasting, multi-week templates — and schedule-adjacent messaging is enough. Stay if payroll/POS integrations around the roster are load-bearing. Pebb does not replace a payroll engine.

Pricing and plans

USD. When I Work figures from wheniwork.com/pricing as of September 2026 (re-check before you sign; their page uses a Time Tracking & Attendance toggle).

Published base tiers (toggle off on the page we reviewed): Essentials $2.50, Pro $5, Premium $8 per user/month.

Essentials lists: unlimited users, auto scheduling, multi-week and multi-location scheduling, templates, forecast tools, in-app team messaging, OpenShifts and shift swapping, help center/live chat, payroll and POS integrations. Pro adds advanced scheduling, rules, role permissions, labor sharing, custom unit forecasting, callout reporting within 24 hours, custom reporting, overlapping OpenShifts, time-zone toggle. Premium adds API key access, webhooks, and SAML/SSO.

Time Tracking & Attendance: official page shows an on/off toggle on every plan. Third-party reports with the toggle on show $4 / $7 / $10 per user. Treat as reported; re-verify on wheniwork.com/pricing. Their FAQ also says plans include time and attendance while the UI presents a toggle.

Trial: 14 days, full access, no credit card (per their pricing FAQ). No permanent free plan. Some secondary reviews say seats bill in blocks of five — UNKNOWN on the public pricing page we fetched.

Pebb: no free plan. Basic $2.50/user. Premium $4/user. Clock-in and timesheets sit on Basic — not a separate attendance SKU. Full trial, no card. See Pebb pricing. Related: Homebase alternative, Deputy alternative, Connecteam alternative.

Ten and twenty-five people

At ten people: When I Work Essentials $25 (reported $40 with TT if $4 holds); Pro $50 (reported $70 with TT). Pebb Basic $25, Premium $40. Same low-tier sticker — gap is product shape.

Setup (25 people) | When I Work (list) | Pebb

Essentials only | $62.50 | Basic $62.50

Essentials + TT (reported $4) | ~$100 | Basic includes clock-in

Pro | $125 | Premium $100

Pro + TT (reported $7) | ~$175 | Premium $100

Premium (+ TT reported $10) | $200 (~$250) | Premium $100

When I Work meters scheduling depth and often an attendance toggle. Pebb meters seats for chat, Spaces, and Premium ops tools at $4.

Pros and cons

Pebb

Pros: Per-user price; second warehouse = a Space. Unlimited Spaces. Chat org-wide; Time Off org-wide on Premium. Tasks, forms, wiki, analytics, SSO on Premium. GPS clock-in ± near-branch on Basic. Open shifts. Full trial, no card.

Cons: No free plan. Not When I Work’s auto-scheduling + labor-forecast center. No payroll, LMS, or ATS. GPS stamp only — not breadcrumbs. Offline does not fully work.

When I Work

Pros: Scheduler-first depth from Essentials (auto scheduling, OpenShifts, templates, forecasting, multi-location). Transparent per-user list from $2.50; Pro/Premium unlock rules, labor sharing, custom reporting, API/SSO. In-app messaging next to the roster; GPS/geofencing clock-ins marketed with time tracking. Payroll/POS integrations (they do not process payroll themselves). 14-day trial, no card.

Cons: Product center is the schedule; messaging is schedule-adjacent — not calls, wiki, or Spaces. Time tracking is a pricing-page toggle; effective $/user may jump (reported to $4 / $7 / $10). No permanent free plan. At 25–80 people, Pro/Premium + attendance can land above Pebb Premium while tasks/wiki/calls stay elsewhere.

Who each is for

Pebb: 11–80 people, frontline plus a small office — construction, field, security, warehouse, multi-location, café/retail floors that need one login for “who’s on,” “clock in,” and “tell the team.” Teams splitting WhatsApp / a schedule tool / a drive. Spaces per site without a second hub or location SKU.

When I Work: Teams whose bottleneck is building and repairing the schedule; hourly ops that want OpenShifts, labor tools, and punch/export next to the roster; operators who bought scheduling depth and payroll/POS sync and do not need wiki, calls, or org-wide rooms.

If hub pricing is the other quote: Pebb vs Connecteam, Connecteam alternative, Connecteam pricing hubs. Compliance scheduler: Pebb vs Deputy, Deputy alternative. Per-location tax: Pebb vs Homebase, Homebase alternative. Verticals: construction, warehouse, security, nonprofit.

Feature by feature

Clock-in and GPS

Winner: When I Work if GPS/geofencing time clock + labor reports around the schedule are the primary desk. Pebb if the punch must sit next to org-wide chat across Spaces.

When I Work markets GPS clock-ins and geofencing with time tracking (confirm on trial which plan/toggle unlocks it). Pebb GPS-stamps the punch with optional near-branch — not live tracking, not telematics. Most multi-gate ops need “they punched at the place” in the same app as chat.

Shift scheduling

Winner: When I Work if auto-scheduling, forecasting, and labor rules are the hard problem. Pebb if people seeing the roster and talking about it across Spaces is the hard problem.

When I Work’s center of gravity is the schedule. Pebb includes shifts and open shifts on Basic and Premium. We will not pretend Pebb is a labor-forecast engine. The closer who never saw the swap is usually a communication failure.

Chat, calls, PTO, tasks, wiki

Winner: Pebb. When I Work messaging is useful schedule chatter — not voice/video, wiki, or Spaces. Pebb chat is org-wide on Basic; Premium adds calls, feed, Time Off, tasks, forms, wiki at $4. No second product to assign a walkthrough checklist.

Payroll and hiring

Winner: Neither as “Pebb payroll.” When I Work if payroll/POS integrations are load-bearing. Neither is your paycheck processor. When I Work integrates/exports (Rippling promotion appears on their pricing page). Pebb timesheets leave the building. No ATS, no LMS.

Spaces vs schedules

Winner: Pebb for multi-site rooms. When I Work for multi-location schedules as the product. A Pebb Space is a room you turn tools on for — not an extra subscription. Chat and Time Off are org-wide.

What a week looks like on Pebb

Monday the GM drops next week’s roster in each site Space; open shifts sit for pickup. Tuesday a lead clocks in with a GPS stamp and optional near-branch check. Wednesday a checklist form lands in the site Space. Thursday Time Off on Premium shows against the roster. Friday timesheets close; chat never left the app, and a Premium DM can call from the thread instead of WhatsApp. No separate attendance tier just to punch.

Setup and switching

Create a workspace. Invite with a link. Space per site or crew. Floor Spaces for shifts/clock-in; Managers Space for leads. Chat is org-wide. Run a week in parallel if needed. Keep When I Work if forecasting or payroll export still own that desk. Trial is the full product. No card.

Who should stay put

Stay if auto-scheduling, OpenShifts, and labor forecasting are why managers live in the tool. Stay if payroll/POS integration is load-bearing and light messaging is enough. Stay if Pro/Premium API, webhooks, or SAML are already wired and communication outside the schedule is solved. Everyone else who bought When I Work as “the employee app” and still runs WhatsApp + a drive for everything that is not a shift — this is the all-in-one version of that job.

FAQ

Is Pebb cheaper than When I Work? At ten people, Essentials and Pebb Basic can match at $25. At twenty-five, Pro/Premium plus reported time-tracking prices often land above Pebb Premium ($100). Re-check When I Work pricing with the attendance toggle in the state you will buy.

Does Pebb have a free plan? No. Basic $2.50/user. Premium $4/user. Full trial, no card. When I Work also has no permanent free plan — 14-day trial, no card.

Does When I Work include time tracking in the $2.50 price? Their page shows a Time Tracking & Attendance toggle. FAQ copy says plans include time and attendance. Third parties report Essentials rising to $4 with the toggle on. Marked UNKNOWN until you confirm in-browser.

Does Pebb do payroll? No. When I Work integrates/exports; it does not process payroll as the paycheck engine. No LMS, no ATS on Pebb.

Do we need Premium? Basic: chat, shifts, clock-in, timesheets, directory. Premium: calls, feed, PTO, tasks, forms, wiki, analytics, SSO.

Does Pebb track people live? No. GPS stamp plus optional near-branch. Not breadcrumbs.

Does Pebb work offline? Not fully. Mobile needs a connection.

How are Spaces different from When I Work locations? Spaces are unlimited rooms on Basic and Premium — not billed storefronts. When I Work multi-location is about schedules and labor sharing.

How fast can we switch? Invite link, Spaces per site, week in parallel. Pricing, then Start full trial — no card.

One app. Not a scheduler plus three other tabs.

Twenty-five people. Chat, shifts, punches, and (on Premium) the ops tools — one seat price.

Start full trial — no card · See pricing