Square Payroll vs Heartland 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…
Heartland Payroll
Starting at Contact for pricing
- Medium Business
- Small Business
Heartland Payroll is a payroll management software for small and medium sized companies. It handles all your payroll processing requirements such as bi-weekly, monthly or yearly paychecks, cost accounting and tracking of…
Square Payroll leads on user satisfaction with a 5.0-star rating across 15 reviews.
Spotsaas Analysis
Square PayrollHeartland Payroll
The core difference between Square Payroll and Heartland Payroll lies in their target employee range and integration capabilities; Square Payroll is tailored for small to medium service businesses with a focus on simplicity and integration with Square POS, while Heartland Payroll offers robust support and automation for small to mid-sized businesses across various industries. Ideal buyers for Square Payroll are business owners and managers in service sectors with 1-100 employees, whereas Heartland Payroll is best suited for payroll managers and HR directors in businesses with 20-500 employees.
- Best for small to medium service businesses - Ideal for businesses with hourly or tipped employees - Seamless integration with Square POS - Simple payroll and time tracking features - Suitable for various service-based industries - Priced at $34
- Best for small to mid-sized businesses - Strong support and streamlined payroll processes - Automated tax filings included - Integrated payment processing capabilities - Suitable for diverse industries like healthcare and manufacturing - Company size range of 20-500 employees
Square Payroll vs Heartland Payroll — at a glance
| Feature | Square Payroll | Heartland Payroll |
|---|---|---|
| Rating | 5.0 / 5 | 4.6 / 5 |
| Reviews | 15 | 118 |
| Starting price | $34 /User/Month | Contact for pricing |
| Free trial | Yes | No |
| Free version | No | No |
| Best for | Large Enterprises, Medium Business, Small Business | 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 | 24/7 (Live rep) |
| Certifications | SOC 2, GDPR | — |
| Data residency | US | US |
Key differences between Square Payroll and Heartland Payroll
- Pricing: Square Payroll starts at $34 /User/Month. Heartland Payroll pricing is not publicly listed.
- Free trial: Square Payroll offers a free trial; Heartland Payroll does not.
- Target audience: Square Payroll is built for Large Enterprises and Medium Business, while Heartland Payroll targets Medium Business and Small Business.
- User satisfaction: Square Payroll scores higher with a 5.0-star average.
- Deployment: Square Payroll supports SaaS/Web/Cloud, Mobile - Android, Mobile - iOS; Heartland Payroll supports SaaS/Web/Cloud.
Square Payroll vs Heartland Payroll — find the better fit before you commit.
Which tool fits your team best
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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
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Square Payroll vs Heartland 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.
Best for small to mid-sized businesses needing streamlined payroll with strong support.
- You run a retail, hospitality, or healthcare business with 20-500 employees.
- You want automated tax filings and integrated payment processing to reduce manual work.
- You value responsive, knowledgeable payroll specialists for personalized customer support.
- Your company is a large enterprise with complex payroll needs requiring high customization.
- You need a highly customizable payroll entry and reporting system beyond standard options.
Square Payroll: Best for small to medium service businesses needing simple payroll and time tracking. Heartland Payroll: Best for small to mid-sized businesses needing streamlined payroll with strong support.
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 | Heartland Payroll is a payroll management software for small and medium sized companies. It handles all your payroll processing requirements such as bi-weekly, monthly or yearly paychecks, ... Read More about Heartland Payroll |
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Entry Level Pricing |
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Free Trial Availability |
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SpotScoreWhat's this? ↗ | 8.8/10 | 8.7/10 |
User RatingsBased on verified Spotsaas reviews | ||
Best Company Size | 1-100 employeesMedium Business | 20-50 employees51-500 employees |
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.
- Integrated Payments & Payroll: Combines payroll with Heartland's payment processing, simplifying employee compensation and business transactions.
- Compliance & Tax Filing: Automates federal, state, and local tax filings, helping reduce compliance risks and administrative workload.
- User-Friendly Platform: Designed to simplify payroll with easy-to-use dashboards, direct deposit options, and responsive customer support.
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
- 20–500 employees
- Retail, hospitality, healthcare, manufacturing, and small to mid-sized businesses
- Payroll Managers, HR Directors, Finance Officers, Business Owners, and Operations Managers
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.
- Businesses seeking deeper integration between payment processing and payroll may explore other all-in-one providers.
- Companies requiring advanced HR management, benefits administration, or time tracking may consider broader HCM platforms.
- Firms with multi-state or complex compliance needs might look for payroll solutions specializing in regulatory support.
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How do Square Payroll and Heartland Payroll Compare on Features?
Total Features | 13 Features | 12 Features |
|---|---|---|
Unique Features | No unique features | No unique features |
Get Quote | Get Quote |
Compare Square Payroll and Heartland 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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Pricing Page |  | Pricing information not available |
Square Payroll vs Heartland Payroll: Other Details
Organization Types supported |
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Platforms Supported |
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Modes of support |
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API Support |
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Get help choosing | Get help choosing |
Square Payroll vs Heartland Payroll Security & Compliance
Certifications, data handling, and security controls for IT and compliance evaluators.
SOC 2 | ✓ Yes | — |
|---|---|---|
HIPAA | ✗ No | ✗ No |
GDPR | ✓ Yes | — |
Single Sign-On (SSO) | ✓ Yes | — |
Multi-Factor Auth (MFA) | ✓ Yes | — |
Data Encryption | ✓ Yes | — |
Audit Logs | ✓ Yes | — |
Data Residency | 🇺🇸 US | 🇺🇸 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 Users appreciate the user-friendly platform and strong customer service but note onboarding challenges and portal access issues. 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 |
| Negative 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 |  2 Videos |
Top Alternatives to Square Payroll and Heartland 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 Heartland Payroll?
- Square Payroll edges out the other on user ratings (5.0 vs 4.6). That said, the best pick depends on your use case — use the comparison tables above to evaluate each dimension.
- Do Square Payroll and Heartland Payroll offer a free trial?
- Square Payroll offers a free trial. Heartland Payroll does not.
- What is the starting price of Square Payroll vs Heartland Payroll?
- Square Payroll starts at $34 /User/Month. Heartland Payroll starts at Contact for pricing.
- 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 Heartland Payroll?
- Top alternatives to Heartland Payroll include QuickBooks Payroll, OnPay, Square Payroll, Patriot Payroll, SurePayroll.