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
Which Should You Choose?
Choose Streak if...
- →Solopreneurs and small teams that manage all business communication through Gmail
- →Gmail users wanting CRM built into their inbox
- →Small teams managing deals without switching apps
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