Calendly vs Upserve POS vs SumUp vs Square Point of Sale Comparison
Calendly
Starting at $8 /User/Month
- Free Trial
- Individuals
- Freelancers / Consultants
Calendly is free meeting scheduling software that dramatically increases your booking rates with Web-based meetings, while making it easy to book face-to-face time with busy clients. With Calendly, you can book an appoin…
Upserve POS
Starting at $59 /Month
- Large Enterprises
- Medium Business
Introducing Upserve POS, the ultimate restaurant management solution. With its user-friendly interface and advanced features, it helps streamline your business operations and boost productivity. This innovative POS syste…
SumUp
Starting at $0 /month
- Large Enterprises
- Medium Business
SumUp is a trusted financial technology company operating in 32 countries across three continents. We aid small business owners by making it quick, secure, and cost-effective to accept card payments online, in-app, and i…
Square Point of Sale
Starting at Contact for pricing
- Large Enterprises
- Medium Business
Square Point of Sale, the ultimate choice for businesses searching for an easy-to-use POS system. With its user-friendly design, you can effortlessly process transactions, track customer purchases, and collect feedback f…
Calendly leads on user satisfaction with a 4.5-star rating across 1,680 reviews.
Calendly vs Upserve POS vs SumUp vs Square Point of Sale — at a glance
| Feature | Calendly | Upserve POS | SumUp | Square Point of Sale |
|---|---|---|---|---|
| Rating | 4.5 / 5 | 4.2 / 5 | 4.0 / 5 | 4.5 / 5 |
| Reviews | 1,680 | 531 | 4 | 518 |
| Starting price | $8 /User/Month | $59 /Month | $0 /month | Contact for pricing |
| Free trial | Yes | No | No | No |
| Free version | No | No | No | No |
| Best for | Individuals, Freelancers / Consultants, Large Enterprises | Large Enterprises, Medium Business, Small Business | Large Enterprises, Medium Business, Small Business | Large Enterprises, Medium Business, Small Business |
| Category | Appointment Scheduling Software | POS Software | POS Software | POS Software |
| Integrations | — | — | 8+ apps | — |
| Platforms | SaaS/Web/Cloud, Mobile - Android, Mobile - iOS | SaaS/Web/Cloud, Mobile - Android, Mobile - iOS | SaaS/Web/Cloud, Mobile - Android, Mobile - iOS | SaaS/Web/Cloud, Mobile - Android, Mobile - iOS |
| API | Available | Available | Available | Available |
| Support modes | Business Hours, Online | 24/7 (Live rep), Online | Business Hours, Online | Business Hours, Online |
| Certifications | SOC 2, GDPR | — | SOC 2, GDPR | SOC 2, GDPR |
| Data residency | US | Global | Global | US |
Key differences between Calendly and Upserve POS
- Pricing: Calendly starts at $8 /User/Month, while Upserve POS starts at $59 /Month.
- Free trial: Calendly offers a free trial; Upserve POS does not.
- Target audience: Calendly is built for Individuals and Freelancers / Consultants, while Upserve POS targets Large Enterprises and Medium Business.
- User satisfaction: Calendly scores higher with a 4.5-star average.
- Deployment: Calendly supports SaaS/Web/Cloud, Mobile - Android, Mobile - iOS; Upserve POS supports SaaS/Web/Cloud, Mobile - Android, Mobile - iOS.
Compare Calendly vs Upserve POS vs SumUp vs Square Point of Sale — and walk away knowing which one fits.
Which tool fits your team best
Which is actually cheaper for your team size
Where each product wins, per real buyers
Most Appointment Scheduling 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 |
Free PDF comparison
Download this Calendly vs Upserve POS vs SumUp vs Square Point of Sale comparison
Get the full side-by-side as a PDF — these picks plus the top Appointment Scheduling Software tools, with verified ratings, pricing and features.
- Side-by-side on pricing, features & ratings
- Plus the category top 10, scored & ranked
- Emailed to you — no on-screen download
No file downloads on screen — we email it to you. One-click unsubscribe anytime.
Biggest differences
Start here before you go deeper into features.
Best for simple, efficient scheduling with strong calendar integrations.
- You need to streamline meeting bookings and reduce scheduling back-and-forth.
- Your team uses multiple calendar platforms and requires seamless integration.
- You want an easy-to-use tool suitable for freelancers, small businesses, and mid-sized teams.
- You require extensive onboarding support and detailed user training.
- Your organization depends on a large marketplace of third-party app integrations.
Best for restaurants needing fast, intuitive POS with strong customer support.
- You operate a small to medium restaurant, bar, or café seeking streamlined workflows.
- You value quick setup and an easy-to-learn interface for your staff.
- You need reliable offline mode and specialized table marking features.
- You require extensive custom features or advanced POS functionalities.
- You have a very tight budget and need a low-cost POS solution.
Large Enterprises, Medium Business, Small Business
Best for small to mid-sized retail and food businesses needing simple POS.
- You want an easy-to-use POS with quick transaction processing.
- You need integrated inventory management and sales reporting.
- You require mobile device compatibility and hardware like Square Terminal.
- Your business is a large enterprise needing extensive customization.
- You require complex, multi-location inventory management capabilities.
Calendly: Best for simple, efficient scheduling with strong calendar integrations. Upserve POS: Best for restaurants needing fast, intuitive POS with strong customer support.
Description | Calendly is free meeting scheduling software that dramatically increases your booking rates with Web-based meetings, while making it easy to book face-to-face time with busy clients. With ... Read More about Calendly | Introducing Upserve POS, the ultimate restaurant management solution. With its user-friendly interface and advanced features, it helps streamline your business operations and boost ... Read More about Upserve POS | SumUp is a trusted financial technology company operating in 32 countries across three continents. We aid small business owners by making it quick, secure, and cost-effective to accept card ... Read More about SumUp | Square Point of Sale, the ultimate choice for businesses searching for an easy-to-use POS system. With its user-friendly design, you can effortlessly process transactions, track customer ... Read More about Square Point of Sale |
|---|---|---|---|---|
Entry Level Pricing |
|
|
|
|
Free Trial Availability |
|
|
| |
Spotsaas ScoreWhat's this? ↗ | 9.8/10 | 9.1/10 | Not Available | 9.2/10 |
User RatingsBased on verified Spotsaas reviews | ||||
Best Company Size | 1-50 employees51-500 employees | Small BusinessMedium Business | — | 1-50 employees51-500 employees |
Get pricing help | Get pricing help |
Software Demo
Demo |  Calendly has not given any software demo yet If you're the owner of this profile, add your demo.Contact us |
|---|
Need a second opinion?
Get shortlist help from a software advisor
Share your priorities, budget, and team needs, and we’ll help you narrow the options and understand the tradeoffs before you talk to vendors.
- Independent advice — matched to your business
- Understand the tradeoffs before you talk to vendors
- Free 15-min call with a software advisor.
Step 1 of 4
How big is your team?
We tailor recommendations to companies your size.
How do Calendly, Upserve POS, SumUp and Square Point of Sale Compare on Features?
Total Features | 10 Features | 26 Features | 14 Features | 11 Features |
|---|---|---|---|---|
Unique Features | No unique features | No unique features | No unique features | No unique features |
Get Quote | Get Quote |
Compare Calendly, Upserve POS, SumUp and Square Point of Sale 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.
Pricing Option | ||||
|---|---|---|---|---|
Starting From |
|
|
|
|
Pricing Plans |
|
|
| |
Pricing Page |  |  |  |  |
Other Details
Organization Types supported |
|
|
|
|
|---|---|---|---|---|
Platforms Supported |
|
|
|
|
Modes of support |
|
|
|
|
API Support |
|
|
|
|
Get help choosing | Get help choosing |
Security & Compliance
Certifications, data handling, and security controls for IT and compliance evaluators.
SOC 2 | ✓ Yes | — |
|---|---|---|
HIPAA | ✗ No | ✗ No |
GDPR | ✓ Yes | — |
ISO 27001 | ✗ No | — |
Single Sign-On (SSO) | ✓ Yes | — |
Multi-Factor Auth (MFA) | ✓ Yes | — |
Data Encryption | ✓ Yes | — |
Audit Logs | — | — |
Data Residency | 🇺🇸 US | 🌐 Global |
Calendly vs Upserve POS vs SumUp User Reviews & Rating Comparison
User Ratings | 4.5 (based on 518 reviews) | |||
|---|---|---|---|---|
Rating Distribution | ||||
Spotsaas Editor’s POV generated by AI | Buyer sentiment Users generally praise Calendly for its ease of use, efficient scheduling, and strong calendar integrations, though some find onboarding and advanced features limited. What buyers like
Common complaints
| Buyer sentiment Users generally praise Upserve POS for its speed, ease of use, and excellent customer service, though some find it costly and wish for more advanced features. What buyers like
Common complaints
| Buyer sentiment Buyer sentiment is positive across 10049 reviews, with strong overall satisfaction. What buyers like
Common complaints
| Buyer sentiment Buyers generally appreciate Square POS for its ease of use and hardware integration but note limitations in advanced features and pricing clarity. What buyers like
Common complaints
|
Pros and Cons |
|
|
|
|
Positive Reviews | No reviews available for the product | No reviews available for the product | 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 | No reviews available for the product | No reviews available for the product |
Integrations
Integration with other apps | No Integration information available. | No Integration information available. | No Integration information available. |
|---|
List of Customers
Customers | No Customers information available. |  Playa Bowls  Pressbistro  Smoke-shop |  DHL  FLiXBUS | No Customers information available. |
|---|
Media and Screenshots
Screenshots |  1 Screenshots | No screenshots available. |
|---|---|---|
Videos | No videos available. |  3 Videos |
Alternatives
Alternatives |
|---|
Add another option to compare side by side
Search by product name to compare pricing, fit, and buyer feedback in one view.Compare similar software options
Related Blogs and Articles for Pos Software
payment gateway software
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, Calendly or Upserve POS?
- Calendly edges out the other on user ratings (4.5 vs 4.2). That said, the best pick depends on your use case — use the comparison tables above to evaluate each dimension.
- Do Calendly and Upserve POS offer a free trial?
- Calendly offers a free trial. Upserve POS does not.
- What is the starting price of Calendly vs Upserve POS?
- Calendly starts at $8 /User/Month. Upserve POS starts at $59 /Month.
- What are the top alternatives to Calendly?
- Top alternatives to Calendly include Appointy, Acuity Scheduling, Setmore, Microsoft Bookings, Cogsworth.
- What are the top alternatives to Upserve POS?
- Top alternatives to Upserve POS include SumUp, Square Point of Sale, ShopKeep, Lightspeed Retail, SlickPOS.