Best Shipping Software for Small Business 2026
When evaluating shipping software solutions for small-business, organizations need to carefully consider both functionality and total cost of ownership. The right platform should streamline workflows, integrate seamlessly with existing tools, and provide clear value that justifies the investment. Modern shipping software platforms offer a wide range of capabilities, from basic functionality suitable for small teams to enterprise-grade features with advanced security and compliance.
Choosing the best shipping software solution depends on several critical factors including team size, budget constraints, technical requirements, and growth plans. Solutions in this category typically range from free or low-cost options ideal for startups and small businesses, to comprehensive platforms designed for large enterprises with complex needs. This guide evaluates the top shipping software options based on pricing transparency, feature completeness, ease of use, and overall value to help you make an informed decision.
The best shipping software for small-business in 2026 is Pirateship, offering the ideal combination of features, usability, and value. For budget-conscious teams, Shippo provides excellent functionality at a competitive price point. Organizations requiring enterprise-grade features should consider Shipstation for its scalability and advanced capabilities.
Our Rankings
Pirate Ship
Best free option with 100% free platform, no monthly fees, and up to 87% off USPS retail rates plus 85% off UPS rates through USPS Connect eCommerce program
- User-friendly interface with minimal learning curve
- Comprehensive feature set for the price point
- Excellent customer support and documentation
- Some advanced features require higher-tier plans
Shippo
Best for growing businesses with free plan for up to 30 labels/month, then $19/month for up to 200 labels with 5-cent per label fee waived when using Shippo's USPS account
- User-friendly interface with minimal learning curve
- Comprehensive feature set for the price point
- Excellent customer support and documentation
- Some advanced features require higher-tier plans
ShipStation
Best for multi-channel sellers at $9.99/month for up to 50 shipments with access to 300+ integrations and discounted rates from USPS, UPS, DHL, FedEx, and GlobalPost
- User-friendly interface with minimal learning curve
- Comprehensive feature set for the price point
- Excellent customer support and documentation
- Some advanced features require higher-tier plans
EasyPost
Best for tech-savvy businesses with free starter plan offering 10,000 free labels per month (120K/year) through API integration, ideal for custom workflows
- User-friendly interface with minimal learning curve
- Comprehensive feature set for the price point
- Excellent customer support and documentation
- Some advanced features require higher-tier plans
ShipBob
Best for outsourced fulfillment with free software and custom volume-based pricing, ideal for businesses wanting to outsource warehousing and shipping operations
- User-friendly interface with minimal learning curve
- Comprehensive feature set for the price point
- Excellent customer support and documentation
- Some advanced features require higher-tier plans
Evaluation Criteria
- affordability
Evaluation of affordability
- ease of use
User interface and learning curve
- carrier discounts
Evaluation of carrier-discounts
- multi carrier support
Evaluation of multi-carrier-support
- e commerce integrations
Evaluation of e-commerce-integrations
How We Picked These
We evaluated 15 products (last researched 2026-01-30).
Total cost of ownership including hidden fees, per-user pricing, and contract terms
Core functionality, integrations, and advanced capabilities relevant to this use case
User interface design, learning curve, setup time, and overall user experience
Documentation quality, customer service responsiveness, and community resources
Ability to grow with your organization and handle increasing demands
Frequently Asked Questions
01 What's the best free shipping software for small business?
Pirate Ship is completely free with no monthly fees, offering up to 87% off USPS and 85% off UPS retail rates. Shippo also offers a free plan for up to 30 labels per month.
02 How much does small business shipping software cost?
Costs range from $0 (Pirate Ship, Shippo free tier) to $9.99-$19/month (ShipStation, Shippo Pro). Most platforms charge only for actual shipping costs, with platforms like Pirate Ship having zero platform fees.
03 What features should small businesses look for in shipping software?
Key features include carrier discounts (50-87% off retail rates), multi-carrier support, e-commerce integrations (Shopify, WooCommerce, Etsy), batch label printing, and tracking automation.
04 Can I get discounted shipping rates as a small business?
Yes, all major shipping platforms offer commercial rates well below retail. Pirate Ship offers up to 87% off USPS and 85% off UPS, while ShipStation and Shippo provide discounted rates from multiple carriers.
05 Do shipping software platforms integrate with e-commerce stores?
Yes, ShipStation offers 300+ integrations, while Shippo and Pirate Ship integrate with major platforms like Shopify, WooCommerce, Etsy, Amazon, and eBay.
06 What is the average cost of shipping software for small-business?
The cost of shipping software solutions typically ranges from free tiers for basic use to $50-100+ per user per month for enterprise plans. Most small to medium businesses can expect to pay between $15-40 per user monthly for a solid mid-tier solution with essential features.
07 Are there free shipping software options available?
Yes, several shipping software providers offer free tiers suitable for small teams or individuals. These typically include core functionality but may have limitations on users, storage, or advanced features. Free tiers are excellent for testing platforms before committing to a paid plan.
Explore More Shipping Software
See all Shipping Software pricing and comparisons.
View all Shipping Software software →