Heartland Payroll vs Square Payroll Comparison
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
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…
Square Payroll leads on user satisfaction with a 5.0-star rating across 15 reviews.
Spotsaas Analysis
Heartland PayrollSquare Payroll
The core difference between Heartland Payroll and Square Payroll lies in their target user base and functionality; Heartland is tailored for small to mid-sized businesses with more complex payroll needs, while Square focuses on simplicity for smaller service businesses. Ideal buyers for Heartland are those managing larger teams in industries like retail and healthcare, whereas Square is best suited for small businesses, particularly in the service sector, with simpler payroll requirements.
Who should pick which
- Best for small to mid-sized businesses needing streamlined payroll:
- Strong support for payroll managers and HR directors:
- Automated tax filings and integrated payment processing:
- Ideal for retail, hospitality, and healthcare industries:
- Suitable for companies with 20-500 employees:
- Focus on reducing manual work:
- Best for small to medium service businesses:
- Simple payroll and time tracking features:
- Effortless integration with Square POS:
- Ideal for businesses with hourly or tipped employees:
- Suitable for companies with 1-100 employees:
- Targeted at business owners and payroll managers in service sectors:
Heartland Payroll vs Square Payroll — at a glance
| Feature | Heartland Payroll | Square Payroll |
|---|---|---|
| Rating | 4.6 / 5 | 5.0 / 5 |
| Reviews | 118 | 15 |
| Starting price | Contact for pricing | $34 /User/Month |
| Free trial | No | Yes |
| Free version | No | No |
| Best for | Medium Business, Small Business | Large Enterprises, Medium Business, Small Business |
| Category | Payroll Software | Payroll Software |
| Platforms | SaaS/Web/Cloud | SaaS/Web/Cloud, Mobile - Android, Mobile - iOS |
| API | — | Available |
| Support modes | 24/7 (Live rep) | Business Hours |
| Certifications | — | SOC 2, GDPR |
| Data residency | US | US |
Key differences between Heartland Payroll and Square 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: Heartland Payroll is built for Medium Business and Small Business, while Square Payroll targets Large Enterprises and Medium Business.
- User satisfaction: Square Payroll scores higher with a 5.0-star average.
- Deployment: Heartland Payroll supports SaaS/Web/Cloud; Square Payroll supports SaaS/Web/Cloud, Mobile - Android, Mobile - iOS.
Heartland Payroll vs Square 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
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Heartland Payroll vs Square Payroll: Biggest differences
Start here before you go deeper into features.
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.
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.
Heartland Payroll: Best for small to mid-sized businesses needing streamlined payroll with strong support. Square Payroll: Best for small to medium service businesses needing simple payroll and time tracking.
Description | 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 | 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 |
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Entry Level Pricing |
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Free Trial Availability |
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SpotScoreWhat's this? ↗ | 8.7/10 | 8.8/10 |
User RatingsBased on verified Spotsaas reviews | ||
Best Company Size | 20-50 employees51-500 employees | 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
- 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.
- 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.
Best fit
- 20–500 employees
- Retail, hospitality, healthcare, manufacturing, and small to mid-sized businesses
- Payroll Managers, HR Directors, Finance Officers, Business Owners, and Operations Managers
- 1–100 employees
- Retail, food service, salons, hospitality, and other service-based small businesses
- Business Owners, Payroll Managers, Accountants, Restaurant Managers, and HR Assistants
Reasons buyers look elsewhere
- 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.
- 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.
Software Demo
Demo |
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How do Heartland Payroll and Square Payroll Compare on Features?
Total Features | 12 Features | 13 Features |
|---|---|---|
Unique Features | No unique features | No unique features |
Get Quote | Get Quote |
Compare Heartland Payroll and Square 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 |  |
Heartland Payroll vs Square 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 |
Heartland Payroll vs Square 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 |
Heartland Payroll User Reviews & Rating Comparison
User Ratings | ||
|---|---|---|
Rating Distribution | ||
Spotsaas Editor’s POV generated by AI | 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
| 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
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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 | No screenshots available. |  6 Screenshots |
|---|---|---|
Videos |  2 Videos |  1 Videos |
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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, Heartland Payroll or Square 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 Heartland Payroll and Square Payroll offer a free trial?
- Square Payroll offers a free trial. Heartland Payroll does not.
- What is the starting price of Heartland Payroll vs Square Payroll?
- Heartland Payroll starts at Contact for pricing. Square Payroll starts at $34 /User/Month.
- What are the top alternatives to Heartland Payroll?
- Top alternatives to Heartland Payroll include QuickBooks Payroll, OnPay, Square Payroll, Patriot Payroll, SurePayroll.
- What are the top alternatives to Square Payroll?
- Top alternatives to Square Payroll include OnPay, APS Payroll, Heartland Payroll, QuickBooks Payroll, Justworks.