Streak vs When I Work
A head-to-head comparison to help you pick the right tool
Last updated: September 14, 2026
Streak is our recommended pick for most teams — solopreneurs and small teams that manage all business communication through gmail.
Try Streak →Read our full Streak review →Streak
Streak is a CRM built directly inside Gmail, allowing users to manage their sales pipeline without ever leaving their inbox. It turns Gmail into a fully functional CRM with pipelines, contact tracking, and email tools. Streak is ideal for solopreneurs and small teams that do all their business communication through Gmail.
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
- ✓Works entirely inside Gmail — zero context switching
- ✓Free plan is genuinely useful for individuals
- ✓Easy to set up in minutes
- ✓Great for solopreneurs and freelancers
Cons
- ✗Only works if your team uses Gmail
- ✗Not suitable for large teams or complex sales processes
- ✗Limited features compared to standalone CRM platforms
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
Streak vs When I Work: Side by Side
| Factor | Streak | When I Work |
|---|---|---|
| User Rating | 4.3/5 ★ | N/A |
| Category | CRM Software | HR Software |
| Pricing Model | Freemium | Paid |
| Starting Price | Free | $2.50/user/mo |
| Best For | Solopreneurs and small teams that manage all business communication through Gmail | Small businesses with hourly or shift-based workers |
| Our Pick | 🏆 Recommended | — |
Streak Features
- ✓Gmail-based pipeline management
- ✓email tracking
- ✓mail merge
- ✓contact management
- ✓workflow automation
- ✓reporting
- ✓collaboration
When I Work Features
- ✓Shift scheduling
- ✓time clock
- ✓team messaging
- ✓attendance tracking
- ✓payroll export
Pricing Comparison
Best Use Cases
Streak
- →Gmail users wanting CRM built into their inbox
- →Small teams managing deals without switching apps
- →Businesses wanting a simple pipeline in Google Workspace
Who Should NOT Use These Tools
Streak is NOT ideal for:
- ✗Teams not using Gmail as their primary email
- ✗Companies needing advanced reporting and forecasting
- ✗Businesses requiring dedicated mobile CRM apps
Integrations
Streak
Gmail, Google Sheets, Google Drive, Zapier, Slack
Our Take
Choose Streak if solopreneurs and small teams that manage all business communication through gmail. Choose When I Work if small businesses with hourly or shift-based workers.
Best For
Solopreneurs and small teams that manage all business communication through Gmail
Best For
Small businesses with hourly or shift-based workers
Also Consider
If neither Streak nor When I Work is the right fit, Monday.com CRM is worth evaluating.
Monday.com CRM
Teams that want CRM and project management combined in one visual platform
From $12/user/mo
Frequently Asked Questions
What is the difference between Streak and When I Work?
Streak is best for solopreneurs and small teams that manage all business communication through gmail. When I Work is best for small businesses with hourly or shift-based workers.
Which is better, Streak or When I Work?
Choose Streak if solopreneurs and small teams that manage all business communication through gmail. Choose When I Work if small businesses with hourly or shift-based workers.
How much does Streak cost?
Streak starts at Free. Pricing model: Freemium.
How much does When I Work cost?
When I Work starts at $2.50/user/mo. Pricing model: Paid.
Who should use Streak?
Solopreneurs and small teams that manage all business communication through Gmail
Who should use When I Work?
Small businesses with hourly or shift-based workers