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Free vs. Paid Shipping Software: Which Really Costs More?

Text in purple saying "what's the real cost of free shipping platforms". A young woman with overalls and tied back caramel brown hair looking at clipboard and holding a pencil near her chin. There's also a small , brown package on the a table beside her, suggesting she is shipping items.

Do I Choose Free or Paid Shipping Software for My Small Business?

You’re a small business owner. You want to make your shipping process more efficient. To save time and money. The solution? Shipping software, obviously! But do you choose free or paid shipping software? Seems like a no brainer. Small business means a smaller budget. And free is always better, right? Well, that’s not necessarily true…

Free shipping software can often lack features, which costs users more time and money. Below, you’ll find a comparison of’s paid Executive Plan vs. Pirate Ship’s free software. And by the end, you’ll be able to answer your questions. Do I choose free or paid shipping software? And which one really costs more?

Paid Shipping Software - Executive Plan


$29 Per Month for Unlimited Shipping (or $22 P/M with yearly billing)

Summary’s Executive Plan is the most affordable and comprehensive software around vs. other paid shipping platforms. For just $29, users can access unlimited shipping, HUGE discounts on UPS and USPS labels, 2-click home pick-up, and way more. And you really don’t need to be a tech geek to use the software!

Slick automations and robust tools for order and inventory management will save SMB’s hours a week on shipping. To add to that, includes simple yet powerful marketing tools. The Rewards and Email tools are ideal for small retailers looking for an easy way to engage customers and grow those profit margins.

Overall, is a true all-rounder that offers way more value than its $29 p/m. And it’s the perfect solution for small business owners looking to scale. Keep reading below for a more detailed breakdown of’s standout features. 👇

Standout Features

Print hugely discounted shipping labels in just 3 clicks and request a home pick-up in 2!

Users of can print heavily discounted UPS and USPS shipping labels in just 3 clicks. That includes up to 77% off UPS!

To add to that, they can even request home pick-ups in just 2 clicks. This way, they can ship from home, avoid post office queues, and cut their shipping time by 90%.

Slick automations, simple layout and powerful order and inventory management features integrates with multiple eCommerce platforms like Spotify, Square, PayPal, Etsy, and more. This means that users can connect their brand and the software will auto import all your customer order info! The result? No more spending hours on end manually entering customer orders.

Plus, the powerful features for order and inventory management make the platform a winner. makes it easy to combine multiple orders into one shipment in just a few clicks. As well as print multiple shipping labels, pack lists and packing sheets at once with batch processing.

Robust and easy-to-use small business tools

There are also awesome add-on small business growth tools on’s Executive Plan. And they’re comprehensive, while not being too techy.

The Email Marketing Tool allows users to set up ready-to-go templates and automated emails. This way, users can keep buyers engaged with personalized messages. And hugely cut their time spent sending emails at the same time.

Meanwhile, the Rewards Tool allows sellers to assign points for purchases and automatically tracks customer progress. A simple “set it and forget it”. Shoppers are twice as likely to buy more products from a brand if they offer a rewards program. So it’s an excellent tool to help grow profits.

Awesome and comprehensive customer support offers quick customer support via live chat, email, and phone that is second to none.

"I just started using, and the support from the help desk and others has been top notch! Thank you!!"
Jaclyn Roeber, SeneGence seller and user

Simple returns management

Processing returns with is super easy. Now, customers want simple and speedy returns - the software really helps you deliver that.

In-house shipping insurance Included

The Executive Plan automatically includes the’s own Delivery Guarantee for each shipment! So if your package is lost, stolen, or broken, will refund you the cost. How cool is that?


  • Simple layout and easy to use

  • Heavy discounts on UPS (up to 77% off!) and USPS labels, as well as cubic discounts

  • Unlimited shipping for just $29/month

  • Request next day pickup from home in just 2 clicks

  • Excellent customer support via live chat, email, and phone

  • Connects with major eCommerce platforms such as Spotify, Square, PayPal, and Etsy

  • Awesome add-on SMB growth tools including email marketing and rewards tool

  • Powerful features for order and inventory management

  • Comprehensive reporting features

  • Quickly print shipping labels in 3 clicks

  • Slick automations that take away the need for manual data entry

  • Order tracking and delivery notifications

  • Ship mobile app for on-the-go order tracking


  • No international shipping (yet)


Free Shipping Software - Pirate Ship


Free… Obviously. 😉


Pirate Ship is a free shipping software for small businesses. And it deserves some kudos - it’s a decent free solution. Users can compare the best available rates, access big discounts on UPS & USPS labels, and arrange home pick-ups. Pirate Ship also has other features like the ability to import orders, address validation, and order tracking. Plus, the software is pretty easy to use.

However, while Pirate Ship does an ok job with the basics, it isn’t as feature rich as Customer service is limited to chat and email. In addition to this, Pirate Ship doesn’t offer tools with add-on value like’s email and rewards tools. And integrations with major platforms like PayPal and Square are missing.

To add to that, customers have reported issues with importing larger orders from spreadsheets or eCommerce stores. Batch buying labels has also proved difficult among Pirate Ship users. Plus, reviews show issues with processing shipping insurance claims.

Standout Features

Free and easy to use, large discounts on shipping rates, and the ability to ship from home

Pirate Ship is free to use with no additional fees. And it offers big discounts on UPS & USPS labels. Users can find the cheapest and fastest shipping rates available and order free home pick-ups.

Automatic address validation, save and auto-complete, and presets for frequently shipped packages

The platform validates addresses, preventing shipping errors when typing in an address. Pirate Ship also remembers previous shipping addresses and suggests addresses when you're typing.

And users can save package presets with their most common shipping settings. This can be handy when you ship a lot of the same product.

Order tracking and ability to schedule when you want tracking emails to be sent

Pirate Ship offers the ability to see tracking updates from UPS and USPS. Users can also schedule tracking emails and notifications to be sent to their customers.

However, this can only be done on the desktop app. Pirate Ship doesn’t offer a mobile tracking app.

Integrated shipping reports

The free software also has reports feature where users can access their shipping and payment history.


  • Free

  • Heavily discounted UPS & USPS Rates

  • Software finds cheapest and fastest shipping rates for you

  • Import orders from spreadsheets or eCommerce store

  • Request home pick-up

  • Handful of eCommerce integration options including Etsy, eBay, and Shopify

  • Automatic address validation & correction


  • No phone support

  • No mobile app for on-the-go order tracking

  • Not as feature rich as paid platforms like

  • Only basic features for order and inventory management

  • Missing tools that add extra value like’s email and rewards tools

  • Customers report problems with importing larger orders

  • Batch buying labels can be difficult

  • Reviews show issues with shipping insurance claims

  • No integrations with major POS such as Square & PayPal

Conclusion - Free Isn’t Always Better and Paid Pays Back

Free shipping software may seem appealing at first. Especially for small business owners. But the cost of the functionality and features you will lose out on is far greater than a monthly subscription cost. They’re ok for starting out, but as soon as orders increase, SMB’s find themselves needing to look elsewhere for a more efficient shipping solution.

On the other hand,’s Executive Plan is perfect for small businesses looking to scale. Compared to free software, the features and support are a lot more comprehensive. There’s also the added value of more customer support options, in-house shipping insurance, and powerful rewards and email tools. At $29 p/m it’s a steal. And the richer features will pay users back way more in time and money.

All in all, is the ideal option for SMB’s for now and for the future.

Test the Waters - Try the Ship.Com Platform for Free Today!

Choosing your go-to shipping software is a big decision. That’s why offers a 14 Day Free Trial with no obligation. As well as access to the top tier subscription. That way, users get the full experience of using the software.

By starting your free trial today, you’ll be able to:

  • Get $15 shipping credit and ship your first package for FREE. 🎉

  • Access the lowest shipping rates (up to 77% off) on the planet and increase your profit margins. 🤑

  • Cut your shipping time by 90% and win back family time by shipping orders in just 3 clicks and scheduling home pick-ups. 🏠 🚚

  • Improve the accuracy of shipments and reduce delivery errors. 👏 🤩

  • Increase customer retention and reduce marketing costs with an easy-to-use rewards tool. ⭐

Take advantage of all these benefits now, for FREE…


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