Best Of small business shipping software comparison

Best Shipping Software for Small Business in 2026

Discover the top shipping software platforms that can save your small business time and money. We compare pricing, features, and ease of use.

By Top Shipping Service Team Published January 24, 2026 Updated February 9, 2026

Why Small Businesses Need Shipping Software

If you're still manually creating shipping labels through carrier websites, you're wasting valuable time and money. Modern shipping software can save small businesses 20-50% on shipping costs through discounted carrier rates, while automating the entire label creation and tracking process.

In this guide, we'll compare the top shipping software platforms specifically from a small business perspective, focusing on ease of use, affordability, and the features that matter most when you're shipping under 1,000 packages per month.

Our Top 5 Picks

1. Pirate Ship - Best Free Option

Pirate Ship is the clear winner for small businesses on a tight budget. It's 100% free with no monthly fees, no per-label charges, and no markup on carrier rates. You get the cheapest possible USPS and UPS rates with zero overhead.

Best for: Businesses shipping under 200 packages/month who primarily use USPS and UPS.

2. Shippo - Best Pay-Per-Label

Shippo's free plan charges just $0.05 per label with no monthly minimum. This makes it perfect for businesses with variable shipping volumes. You also get access to up to 90% off USPS rates and a clean, intuitive interface.

Best for: Startups and businesses with variable or growing shipping volumes.

3. ShipStation - Best for Growth

ShipStation's Starter plan at $9.99/month provides 50 shipments and access to their powerful platform. As your business grows, you can seamlessly upgrade to handle thousands of shipments with automation and multi-channel support.

Best for: Businesses planning to scale and needing advanced features like automation rules.

4. Easyship - Best for International

If you ship internationally, Easyship is worth considering. They pre-calculate duties and taxes, offer 250+ courier solutions, and provide transparent landed cost calculations.

Best for: Businesses with significant international shipping needs.

5. ShipBob - Best for Outsourced Fulfillment

If you'd rather not handle shipping at all, ShipBob provides full third-party fulfillment. They store your inventory and handle the entire pick, pack, and ship process.

Best for: Businesses shipping 200+ orders/month who want to outsource logistics.

How to Choose

Consider these factors when selecting shipping software:

  1. Volume: How many packages do you ship per month?
  2. Budget: Can you afford a monthly subscription, or do you need free/pay-per-use?
  3. Carriers: Do you need just USPS/UPS, or also FedEx and DHL?
  4. Sales Channels: Do you sell on multiple platforms (Shopify, Amazon, eBay)?
  5. Automation: Do you need rules to automate carrier selection and label printing?

The Bottom Line

For most small businesses just getting started, Pirate Ship is the best choice - it's free, simple, and offers the cheapest rates. As your business grows past 200-500 shipments per month and you need more features, consider upgrading to Shippo or ShipStation.