Oyster vs Square: Which Should You Choose in 2026?
Choosing between Oyster and Square comes down to understanding what each tool does best. This comparison breaks down the key differences so you can make an informed decision based on your specific needs, not marketing claims.
Short on time? Here's the quick answer
We've tested both tools. Here's who should pick what:
Oyster
Global employment platform
Best for you if:
- • You want the higher-rated option (8.6/10 vs 8.2/10)
Square
Payment processing and POS systems
Best for you if:
- • You want to try before committing
| At a Glance | ||
|---|---|---|
Price | Paid | Free + Paid |
Best For | Finance | Finance |
Rating | 86/100 | 82/100 |
| Feature | Oyster | Square |
|---|---|---|
| Pricing Model | Paid | Freemium |
| Editorial Score | 86 | 82 |
| Community Rating | No ratings yet | No ratings yet |
| Total Reviews | 0 | 0 |
| Community Upvotes | 0 | 0 |
| Categories | Finance | FinanceE-commerce |
Understanding the Differences
Both Oyster and Square solve similar problems, but they approach them differently.Oyster positions itself as "global employment platform" while Squarefocuses on "payment processing and pos systems". These differences matter depending on what you're trying to accomplish.
When to Choose Oyster
Oyster makes sense if you're looking for a comprehensive paid solution. With a score of 86/100, it's our top pick in this comparison.
When to Choose Square
Square is worth considering if you need a flexible option with both free and paid tiers tool.
Who Should Use What?
Bootstrapped or small team?
Square won't cost you anything to start, which is exactly what early-stage teams need.
We'd pick: Square
Growing fast?
Your team doubled last quarter and you need tools that won't break when you add 50 more people. Oyster handles scale better in our testing.
We'd pick: Oyster
Enterprise with complex needs?
You need SSO, compliance certifications, and a support team that picks up the phone. Oyster is built for organizations like yours.
We'd pick: Oyster
Still not sure? Answer these 3 questions
How much can you spend?
Want to test first? Square has a free tier to get you started.
Do you care what other users think?
Both have similar review counts. Read a few before you commit.
Expert opinion or crowd wisdom?
Our team rated Oyster higher (86/100). But the community has upvoted Square more (0 votes). Pick your source of truth.
Key Takeaways
What Oyster Does Better
- Higher overall score (86/100)
- Our recommendation for most use cases
Consider Square If
- You want to start free and scale later
- Its specific features better match your workflow
- You prefer its interface or design approach
The Bottom Line
If we had to pick one, we'd go with Oyster (86/100). But the honest answer is that "better" depends on your situation. Oyster scores higher in our analysis, but Square might be the right choice if its specific strengths align with what you need most. Take advantage of free trials to test both before committing.
Frequently Asked Questions
Is Oyster or Square better?
Based on our analysis, Oyster scores higher with 86/100. Oyster ispaid while Square is freemium. The best choice depends on your specific needs and budget. We recommend testing both with free trials if available.
Can I switch from Oyster to Square easily?
Migration difficulty varies. Check if both tools support data export/import in compatible formats. Some tools offer migration assistance or have integration partners who can help with the transition.
Do Oyster and Square offer free trials?
Most software in this category offers free trials or free tiers. Oyster is paid with potential trial.Square is freemium with a free tier. Visit their websites for current trial offers.