Pilot vs When I Work
A head-to-head comparison to help you pick the right tool
Last updated: April 30, 2026
Pilot
Pilot is a managed accounting service that combines software with a dedicated team of bookkeepers to handle your books each month. Built for startups and small businesses that want accounting done for them.
When I Work
When I Work is an employee scheduling and time tracking platform designed for hourly and shift-based teams. It makes it easy for managers to build schedules, communicate with staff, and track attendance. When I Work is one of the most affordable scheduling tools on the market.
Pros
- ✓Fully managed bookkeeping service
- ✓Dedicated finance experts included
- ✓Built specifically for startups
- ✓Integrates with common startup tools
- ✓Good for venture-backed companies
Cons
- ✗More expensive than DIY software
- ✗Less control over day-to-day bookkeeping
- ✗Not suited for businesses wanting to manage their own books
- ✗US-focused
Pros
- ✓Very affordable pricing starting at just a few dollars per user
- ✓Easy-to-use scheduling with drag-and-drop interface
- ✓Good team messaging and shift swap tools
- ✓Simple time clock with GPS tracking
Cons
- ✗Limited features beyond scheduling and time tracking
- ✗No payroll processing or full HR suite
- ✗Reporting is basic compared to more comprehensive workforce tools
Pilot vs When I Work: Side by Side
| Factor | Pilot | When I Work |
|---|---|---|
| User Rating | N/A | N/A |
| Category | Accounting Software | HR Software |
| Pricing Model | Paid | Paid |
| Starting Price | Contact for pricing | $2.50/user/mo |
| Best For | Startups and small businesses wanting fully managed bookkeeping with a dedicated team rather than DIY software | Small businesses with hourly or shift-based workers |
| Our Pick | — | — |
Pilot Features
- ✓Bookkeeping
- ✓tax preparation
- ✓financial reporting
- ✓dedicated bookkeeper
- ✓cash flow management
- ✓integrations
When I Work Features
- ✓Shift scheduling
- ✓time clock
- ✓team messaging
- ✓attendance tracking
- ✓payroll export
Pricing Comparison
Which Should You Choose?
Choose Pilot if...
- →Startups and small businesses wanting fully managed bookkeeping with a dedicated team rather than DIY software
Our Take
Choose Pilot if startups and small businesses wanting fully managed bookkeeping with a dedicated team rather than diy software. Choose When I Work if small businesses with hourly or shift-based workers.
Best For
Startups and small businesses wanting fully managed bookkeeping with a dedicated team rather than DIY software
Best For
Small businesses with hourly or shift-based workers
Also Consider
If neither Pilot nor When I Work is the right fit, Dext is worth evaluating.
Dext
Bookkeepers, accountants, and businesses with high receipt volumes wanting to eliminate manual data entry
From $15/mo
Frequently Asked Questions
What is the difference between Pilot and When I Work?
Pilot is best for startups and small businesses wanting fully managed bookkeeping with a dedicated team rather than diy software. When I Work is best for small businesses with hourly or shift-based workers.
Which is better, Pilot or When I Work?
Choose Pilot if startups and small businesses wanting fully managed bookkeeping with a dedicated team rather than diy software. Choose When I Work if small businesses with hourly or shift-based workers.
How much does Pilot cost?
Visit Pilot website for current pricing.
How much does When I Work cost?
When I Work starts at $2.50/user/mo. Pricing model: Paid.
Who should use Pilot?
Startups and small businesses wanting fully managed bookkeeping with a dedicated team rather than DIY software
Who should use When I Work?
Small businesses with hourly or shift-based workers