Square Payroll
Square Payroll is a full-service payroll software that automates tax filings, employee payments, and benefits management for small businesses using integrated time tracking and point-of-sale data.
Timely
Timely is an AI-powered time tracking software that automatically records everything you work on across your desktop and web applications to eliminate manual timesheets and improve billing accuracy.
Quick Comparison
| Feature | Square Payroll | Timely |
|---|---|---|
| Website | squareup.com | timelyapp.com |
| Pricing Model | Subscription | Subscription |
| Starting Price | Free | $11/month |
| FREE Trial | ✘ No free trial | ✓ 14 days free trial |
| Free Plan | ✘ No free plan | ✘ No free plan |
| Product Demo | ✓ Request demo here | ✓ Request demo here |
| Deployment | ||
| Integrations | ||
| Target Users | ||
| Target Industries | ||
| Customer Count | 0 | 0 |
| Founded Year | 2009 | 2013 |
| Headquarters | San Francisco, USA | Oslo, Norway |
Overview
Square Payroll
Square Payroll simplifies how you pay your team by automating the most complex parts of business ownership. You can pay employees and contractors in just a few clicks, whether they are hourly or salaried. The platform automatically calculates, files, and pays your federal and state payroll taxes, ensuring you stay compliant without manual paperwork. Because it integrates directly with Square POS, your team's hours sync automatically, eliminating the need for manual data entry or messy spreadsheets.
You can manage everything from a single dashboard, including workers' compensation, health insurance, and 401(k) plans. The system supports flexible payment options like Instant Payments, allowing you to send funds to employees the same day they work. Whether you are running a single coffee shop or managing multiple retail locations, you get a straightforward tool that handles the back-office heavy lifting so you can focus on growing your business.
Timely
Timely is an automatic time tracking platform designed to help you capture every billable second without the hassle of manual timers. By using a background application called Memory, it records the time you spend in different documents, meetings, and websites, creating a private timeline of your entire workday. You can then simply drag and drop these activities to log your hours with high precision.
The platform is built for teams and individuals who need to stay focused on their work rather than administrative tasks. It helps you visualize team capacity, track project budgets in real-time, and identify where your time is actually going. Whether you are a freelancer or part of a large agency, you can use these insights to improve your profitability and ensure your clients are billed accurately for every task.
Overview
Square Payroll Features
- Automated Tax Filings Let the software calculate, file, and pay your state and federal payroll taxes automatically to ensure total compliance.
- Time Card Sync Import employee hours directly from Square POS or the Team App to eliminate manual data entry errors.
- Instant Payments Access your funds immediately and pay your team the same day they work using your Square Balance.
- Benefits Integration Offer and manage health insurance, 401(k) plans, and workers' comp directly through your payroll dashboard.
- Contractor Payments Pay your independent contractors via direct deposit and let the system generate and file 1099-NEC forms.
- Employee Mobile App Give your team a dedicated app to track their hours, view pay stubs, and manage their tax forms.
Timely Features
- Automatic Time Capture. Record every app, website, and document you use throughout the day automatically so you never forget a billable hour.
- AI Draft Timesheets. Let the built-in AI categorize your activities and suggest time entries for you to review and approve with one click.
- Project Budget Tracking. Monitor your project spend and progress in real-time to ensure you stay within budget and hit your milestones.
- Team Lead Dashboard. View your entire team's capacity and workload at a glance to prevent burnout and distribute tasks more effectively.
- Private Work Timeline. Keep your recorded data 100% private to you until you choose to share or log it to a project.
- Task Management. Plan your daily tasks and see how your actual time spent compares to your original estimates for better planning.
Pricing Comparison
Square Payroll Pricing
- $5 per person paid monthly
- No monthly base fee
- Direct deposit included
- 1099-NEC generation and filing
- Self-service contractor account
- Everything in Contractor plan, plus:
- $6 per person paid monthly
- Full-service tax filings
- Time card and POS integration
- Health insurance and 401(k) access
- Live phone and chat support
Timely Pricing
- Up to 3 active projects
- Unlimited users
- Automatic time tracking
- AI-drafted timesheets
- Basic reporting
- Integrations with 50+ tools
- Everything in Starter, plus:
- Unlimited active projects
- Project budget tracking
- Team capacity management
- Live project dashboards
- Individual and team reminders
Pros & Cons
Square Payroll
Pros
- Seamless integration with Square Point of Sale
- Automatic tax filing saves hours of manual work
- Simple and transparent per-employee pricing model
- Easy setup process for new business owners
Cons
- Customer support can be difficult to reach
- Limited advanced HR features for large corporations
- Account freezes can occasionally delay payroll processing
Timely
Pros
- Eliminates the need to start and stop manual timers
- Private timeline ensures users feel comfortable with tracking
- Visual interface makes logging hours fast and intuitive
- Accurately captures small tasks that are often forgotten
- Strong integrations with popular tools like Outlook and Slack
Cons
- AI requires a training period to categorize tasks accurately
- Desktop app can occasionally consume significant system resources
- Higher price point compared to basic manual trackers