Square Payroll vs CheckMark Payroll Comparison
Square Payroll
Starting at $34 /User/Month
- Free Trial
- Large Enterprises
- Medium Business
Square Payroll is payroll software for small businesses and sole proprietors, particularly those already running payments or point-of-sale through Square's ecosystem. It automates pay runs, tax filings, and direct deposi…
CheckMark Payroll
Starting at $449
- Free Trial
- Large Enterprises
- Medium Business
CheckMark Payroll is a desktop payroll application for small business owners who want to run payroll in-house without outsourcing. It handles check printing, W-2 generation, and federal tax reports directly from the user…
Square Payroll leads on user satisfaction with a 5.0-star rating across 15 reviews.
Square Payroll vs CheckMark Payroll — at a glance
| Feature | Square Payroll | CheckMark Payroll |
|---|---|---|
| Rating | 5.0 / 5 | 4.2 / 5 |
| Reviews | 15 | 6 |
| Starting price | $34 /User/Month | $449 |
| Free trial | Yes | Yes |
| Free version | No | No |
| Best for | Large Enterprises, Medium Business, Small Business | Large Enterprises, Medium Business, Small Business |
| Category | Payroll Software | Payroll Software |
| Platforms | SaaS/Web/Cloud, Mobile - Android, Mobile - iOS | SaaS/Web/Cloud |
| API | Available | — |
| Support modes | Business Hours | Online |
| Certifications | SOC 2, GDPR | SOC 2 |
| Data residency | US | — |
Key differences between Square Payroll and CheckMark Payroll
- Pricing: Square Payroll starts at $34 /User/Month, while CheckMark Payroll starts at $449.
- User satisfaction: Square Payroll scores higher with a 5.0-star average.
- Deployment: Square Payroll supports SaaS/Web/Cloud, Mobile - Android, Mobile - iOS; CheckMark Payroll supports SaaS/Web/Cloud.
Square Payroll vs CheckMark Payroll — find the better fit before you commit.
Which tool fits your team best
Which is actually cheaper for your team size
Where each product wins, per real buyers
Most Payroll Software tools look identical on paper. This comparison cuts to the differences that matter — pricing structure, team fit, and what real buyers found after signing up.
Biggest differences
Features
Pricing
Buying details
Security
Buyer feedback
Integrations
Product tour
Other options
Talk to an expert Talk to an expert | Talk to an expert Talk to an expert |
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Square Payroll vs CheckMark Payroll: Biggest differences
Start here before you go deeper into features.
Best for small to medium service businesses needing simple payroll and time tracking.
- You run a small to medium business with hourly or tipped employees.
- You want effortless integration with Square POS and existing payroll providers.
- You need a simple, user-friendly payroll system with built-in time tracking.
- You require advanced payroll reporting, customization, or analytics.
- You manage complex pay structures, multiple locations, or international staff.
Large Enterprises, Medium Business, Small Business
Square Payroll typically suits Large Enterprises and Medium Business. CheckMark Payroll tends to fit Large Enterprises and Medium Business better. The right choice depends on your team size, workflow, and whether a free trial matters.
Description | Square Payroll is payroll software for small businesses and sole proprietors, particularly those already running payments or point-of-sale through Square's ecosystem. It automates pay runs, ... Read More about Square Payroll | CheckMark Payroll is a desktop payroll application for small business owners who want to run payroll in-house without outsourcing. It handles check printing, W-2 generation, and federal tax ... Read More about CheckMark Payroll |
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Entry Level Pricing |
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Free Trial Availability | ||
SpotScoreWhat's this? ↗ | 8.8/10 | 8.2/10 |
User RatingsBased on verified Spotsaas reviews | ||
Best Company Size | 1-100 employeesMedium Business | — |
Get pricing help | Get pricing help |
Where each option fits best
See where each product is strongest, which teams it fits, and what causes buyers to keep looking — before you commit.
Based on buyer reviews and verified product data collected by Spotsaas.
Key strengths
- Seamless Integration with Square POS: Syncs easily with Square’s point-of-sale system, making it ideal for hourly or tipped workers in service industries.
- Contractor & Employee Support: Easily pay W-2 employees and 1099 contractors with direct deposit and generate tax forms from a single dashboard.
No key benefits available yet.
Best fit
- 1–100 employees
- Retail, food service, salons, hospitality, and other service-based small businesses
- Business Owners, Payroll Managers, Accountants, Restaurant Managers, and HR Assistants
No best-fit guidance available yet.
Reasons buyers look elsewhere
- Businesses already using Square for POS may seek deeper payroll integrations or industry-specific HR features.
- Employers needing more advanced reporting, analytics, or benefits management might explore broader HR platforms.
- Companies managing multi-state or international employees could require tools with expanded compliance capabilities.
No alternatives guidance available yet.
Software Demo
Demo |
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How do Square Payroll and CheckMark Payroll Compare on Features?
Total Features | 13 Features | 8 Features |
|---|---|---|
Unique Features | No unique features | No unique features |
Get Quote | Get Quote |
Compare Square Payroll and CheckMark Payroll on pricing
Review starting price, plan structure, and free-trial access side by side so you can see which option fits your budget and buying process.
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Square Payroll vs CheckMark Payroll: Other Details
Organization Types supported |
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Platforms Supported |
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API Support |
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Get help choosing | Get help choosing |
Square Payroll vs CheckMark Payroll Security & Compliance
Certifications, data handling, and security controls for IT and compliance evaluators.
SOC 2 | ✓ Yes | ✓ Yes |
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HIPAA | ✗ No | ✗ No |
GDPR | ✓ Yes | — |
Single Sign-On (SSO) | ✓ Yes | — |
Multi-Factor Auth (MFA) | ✓ Yes | — |
Data Encryption | ✓ Yes | ✓ Yes |
Audit Logs | ✓ Yes | — |
Data Residency | 🇺🇸 US | — |
Square Payroll User Reviews & Rating Comparison
User Ratings | ||
|---|---|---|
Rating Distribution | ||
Spotsaas Editor’s POV generated by AI | Buyer sentiment Users appreciate Square Payroll's ease of use, integration capabilities, and time-saving automation, though some desire more advanced features for larger or more complex businesses. What buyers like
Common complaints
| Buyer sentiment Buyer sentiment is positive across 6 reviews, with strong overall satisfaction. What buyers like
Common complaints
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Pros and Cons |
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Positive Reviews | No reviews available for the product | No reviews available for the product |
Media and Screenshots
Screenshots |  6 Screenshots | No screenshots available. |
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Videos |  1 Videos |  1 Videos |
Top Alternatives to Square Payroll and CheckMark Payroll in 2026
Alternatives |
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Disclaimer: This research has been collated from a variety of authoritative sources. We welcome your feedback at [email protected].
Frequently asked questions
- Which is better, Square Payroll or CheckMark Payroll?
- Square Payroll edges out the other on user ratings (5.0 vs 4.2). That said, the best pick depends on your use case — use the comparison tables above to evaluate each dimension.
- Do Square Payroll and CheckMark Payroll offer a free trial?
- Yes, both Square Payroll and CheckMark Payroll offer a free trial.
- What is the starting price of Square Payroll vs CheckMark Payroll?
- Square Payroll starts at $34 /User/Month. CheckMark Payroll starts at $449.
- What are the top alternatives to Square Payroll?
- Top alternatives to Square Payroll include OnPay, APS Payroll, Heartland Payroll, QuickBooks Payroll, Justworks.
- What are the top alternatives to CheckMark Payroll?
- Top alternatives to CheckMark Payroll include Heartland Payroll, OnPay, Square Payroll, Microkeeper, APS Payroll.