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Calculate, Deduct, Deposit: A Square Payroll Review

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Calculate, Deduct, Deposit: A Square Payroll Review

January 2nd, 2024

Every business faces payroll challenges, from Juggling diverse pay structures—commissions, bonuses, and tips to manual tax filling—companies like Square step in to provide flexible and innovative solutions for businesses to overcome any hurdle. Recognized as a user-friendly payroll solution for small to midsize businesses, the company stands out with features like time tracking and seamless integration, added HR benefits, and a comprehensive mobile app.

Discover how Square can transform your business operations. Explore its features, advantages, disadvantages, and prices, ensuring your decisions are well-informed and aligned with your business needs.


Nationwide coverage
Garnishment management
Integrations with third-party applications
On-demand pay & Square Banking
SOC and IRS certifications
Transparent pricing


One plan for employees
Limited employee-type support
Reporting system limitations
Poor fit for large companies
No free trial


Quick Stats

Free Trial
Pricing Option
Per employee
Transparent Pricing
Customer Experience
Trustpilot Score
BBB Rating


Headquartered in San Francisco, Square Inc. was established in 2009 by Jack Dorsey and Jim McKelvey. Initially, the creators envisioned producing and distributing Square POS systems for all types of stores. However, the company has shifted to delivering a comprehensive business technology platform, enabling sellers to seamlessly accept card payments and manage payroll operations. Notably, In 2022, the company attained the ISO 27001 certification, a globally recognized standard for information security management. This certification underscores the company's commitment to maintaining the highest standards in safeguarding information. With an innovative approach to payment processing and business management, they have emerged over the years as a favored choice among small and medium-sized businesses, solidifying their position in the industry.


Square offers several features for businesses, making them a popular choice for efficient payroll management.

Software features

Square's cutting-edge payroll software is equipped with advanced features designed to elevate efficiency and simplify the complexities of payroll management for businesses. 

Time tracking and integration: Their payroll software seamlessly integrates with timecards, tips, and commissions, simplifying the tracking of hours worked and the calculation of payments.

Mobile accessibility: Employees can conveniently clock in and out, track hours, and access their pay stubs using their mobile phones, providing on-the-go accessibility.

Tax filing and compliance management: Square's software automates quarterly and annual tax payments, ensuring compliance with 1099-NEC, 940, 941, 944, W-2, and W-3 forms across all states. With each payroll processing cycle, the software calculates, withholds, and remits payroll taxes to federal and state agencies, saving time and ensuring regulatory adherence.

Team management tools: The software includes team management tools, such as the Square Team app, empowering employees to manage their time, view earnings, and access benefits efficiently.

Other features

Aside from their software, the company offers added versatility, going beyond the basics and offering businesses a little extra in their payroll toolkit.

Adaptable pay structures: Square effortlessly handles intricate pay structures, including multiple pay rates, commissions, bonuses, and tips. This capability provides users with the flexibility needed for diverse compensation models.

Responsive live support: Users can access a live chat feature available on their website during business hours, Monday to Friday, from 6 AM to 6 p.m. PT. These specialists stand ready to assist and guide users through any challenges they may encounter during their payroll processes.

Onboarding assistance: Users benefit from Square's onboarding guidance and customer support services, ensuring a seamless setup process and setting them up for success from the outset.

Comprehensive benefits administration: Square extends its capabilities to cover employer-sponsored and direct-to-employee benefits. This comprehensive approach offers users a holistic solution for effectively managing employee benefits such as health insurance, retirement plans, paid time off, etc.

Payroll enhancers: Square goes beyond basic functionalities, offering users access to additional features such as Cash App and on-demand pay. Moreover, users can enjoy the convenience of free seasonal inactivity, collectively enhancing the overall payroll experience.

Direct deposit or manual check options: Square offers flexibility in payment methods, allowing businesses to pay employees through direct deposit or manual checks based on their preferences.


Square's solutions propel your business a step ahead of the competition, excelling in areas like nationwide coverage, garment management, and integrations, among others, to comprehensively address all your business needs.

Transparent pricing

Square is known for their transparent and straightforward pricing structure. Businesses appreciate the clarity in understanding the costs associated with the payroll service, helping them budget more effectively without unexpected fees or hidden charges.

Nationwide coverage

Square provides nationwide coverage, allowing businesses operating in various states to use the service. This is particularly beneficial for companies with a distributed workforce or those expanding their operations to different regions.

Garnishment management

Square simplifies the complex process of managing wage garnishments. It helps businesses stay compliant with legal requirements by automating the calculation and deduction of garnishments, ensuring accuracy and reducing the risk of errors.

Integrations with third-party applications

Square seamlessly integrates with various software, readily accessible through their dedicated marketplace. This includes seamless integrations with Square partners such as SimplyInsured, QuickBooks Online, Homebase, Next Insurance, and ZipRecruiter.

On-demand pay & Square Banking

Square's On-Demand Pay feature allows eligible team members to access up to 50% of their earned wages, capped at $200 per pay period. This can be done through the Square Team app or online dashboard, with instant payment to Cash App, a linked debit card, or a supported direct deposit bank account.

SOC and IRS certifications

Square holds certifications from reputable organizations, including SOC (Service Organization Control) and the IRS. These certifications testify to the company's commitment to robust security measures, ensuring the protection of sensitive payroll data and full compliance with industry and regulatory standards.

Unique Selling Points

The company distinguishes itself in the market with several unique selling points that provide added convenience and flexibility.

Mobile application

Square offers a mobile application that allows business owners, HR personnel, and employees to access information, make updates, and handle various tasks on the go using their smartphones or tablets. This flexibility aligns with the modern workforce's need for mobility and the ability to manage payroll processes anytime, anywhere.

Added HR benefits

Square offers additional HR services and benefits beyond basic payroll processing. These may include features like employee onboarding, time and attendance tracking, and compliance assistance. By providing a more comprehensive set of HR tools to streamline the broader aspects of workforce management, it becomes a one-stop solution for businesses looking to streamline processes.

Easy cancelation

Square Payroll stands out with its commitment to customer satisfaction, offering an easy cancelation process. The platform understands that business needs may change, and companies may need to adjust their payroll solutions accordingly. The straightforward cancelation process highlights their customer-centric approach.


While Square offers certain advantages, it also has notable drawbacks that require careful consideration.

No free trial

One notable drawback of Square is the absence of a free trial option. Unlike some competitors that offer a trial period for businesses to explore the platform's features and functionality, the company's Payroll lacks this trial, potentially making it challenging for users to assess its suitability for their specific needs before committing to a subscription.

One plan for employees

The company offers a single plan for managing employee payroll. While this simplicity may be suitable for smaller businesses with straightforward needs, it could be limiting for larger enterprises or those with more complex requirements. Companies seeking customization options or scalability might find the singular plan structure restrictive.

Limited employee-type support

Square is designed for businesses filing Form 941 or Form 944 but lacks support for certain employee types, specifically household and agricultural employees. This limitation may pose a significant challenge for companies operating in sectors requiring specialized payroll solutions for these employees.

Reporting system limitations

Users have voiced dissatisfaction with Square's reporting system. A recurring complaint is the lack of functionality that allows users to download and export payroll reports. While reports can be viewed online, the absence of a download option may pose challenges for businesses requiring offline data access or sharing. This limitation could hinder the ease of data analysis and reporting for users.

Poor fit for large companies

Square's pricing structure presents challenges for larger companies as it involves a fixed price and added costs for each employee. This may not align with the volume-based pricing considerations that larger enterprises typically require. As businesses grow, their payroll needs become more intricate, necessitating solutions that offer flexibility in pricing and accommodate the increasing complexity of payroll processes, which Square may not fully provide for larger or rapidly growing enterprises.


Square offers a transparent and affordable pricing model, with a $35 base subscription fee and $6 per employee/contractor paid monthly. This covers unlimited pay runs, automated tax filings, and HR resources. A contractor-only plan is available at $6 per contractor per month. There are no long-term commitments, allowing users to cancel at any time. Their straightforward and competitive pricing makes it an attractive choice for small businesses.

User Experience

Based on user reviews from various platforms, Square has received mixed feedback, reflecting both positive and negative experiences. G2 reviews contribute to Square's overall 4.2-star rating, with users expressing satisfaction over the seamless conversion of time cards into payroll processing and the effectiveness of automated time tracking. Many appreciate the software's capability to alleviate concerns related to tax forms such as W3s, 1099s, quarterly reports, and new hire reports. However, some users note challenges, including a confusing interface, a convoluted setup process, and the inconvenience of manually entering hours for salaried employees. Additionally, the software falls short in allowing the automatic deduction of specific benefits, like select restaurant subscriptions, directly from payroll.

On TrustRadius, where the company holds a 6/10 rating, positive reviews emphasize the software's simplicity and affordability. Users express appreciation for the automatic tax filing feature and constantly praise the support team for their assistance. However, negative feedback on TrustRadius highlights inconveniences such as the unavailability of downloadable payroll reports and the inability to schedule payments, posing challenges for users seeking enhanced functionality.

On Software Advice, the company boasts a 4.7-star rating. Positive reviews commend the software for streamlining processes and eliminating paperwork, attributing the ease of navigation to its user-friendly dashboard. Conversely, negative feedback points out limitations in flexibility and the inability to open closed employee accounts, suggesting areas for improvement.
While customer reviews provide valuable insights, it's crucial to remember that Individual preferences and biases can shape opinions. A comprehensive assessment should also consider the broader reputation of the payroll service.

How Do I Contact Square?

To get in touch with Square, you can contact their customer service teams. For customer support, you can call them at (855) 700-6000, while their sales representatives can be reached at (800) 470-1673. To become a client, you can start the process by filling out the dedicated form on their website. Existing customers can explore additional support options on the Support Center page, connect with the community of sellers, or directly contact support through the website. 
For the latest updates or to engage with the company more casually, check out their social media platforms, including X (Twitter), Facebook, and Instagram. This multi-faceted approach ensures that varied channels are available for effective communication, whether you're seeking assistance, exploring services, or staying connected.


In conclusion, Square is a comprehensive solution for streamlined payroll operations, known for simplicity and innovative features. In 2022, Square solidified its position as an industry leader by obtaining the ISO 27001 certification, showcasing a steadfast commitment to information security. The software's versatile features, including automatic tax filing, mobile accessibility, and team management tools, cater to diverse business needs. While the company excels in nationwide coverage, garnishment management, and integrations, drawbacks include the absence of a free trial and limited plan options. User experiences vary, with positive feedback highlighting simplicity and affordability and noting concerns about report download limitations. Square remains an attractive choice for small businesses, offering competitive pricing and a user-friendly interface.

Empower your decision-making with our comprehensive comparison tool for alternative service providers. Explore our top payroll processing companies through our curated list, ensuring informed choices for your business. Stay ahead of industry trends and insights by delving into the latest specialized articles on our blog.

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