International
  • USA
  • Canada
  • Australia
  • Philippines
  • International
1 (250) 492-8888 sales@windwardsoftware.com Help Center
Windward Software: Business Management Software
  • Home
  • Feature Tour
  • Industry Types
    • Choose your industry col 1
      • Home Goods
      • Building Materials
    • Choose your industry col 2
      • Rental Industry
      • Wheels & Motors
    • Choose your industry col 3
      • Other Retailers
      • Explore All Business Types
  • Resources
    • Help Center
    • Professional Services
    • System Five Add-Ons
    • Training Events & User Conferences
    • Third-Party Integrations
    • Payment Processors
    • Maintenance Contracts
    • Shop for POS Hardware
    • Industry Partners
  • Company
    • About Us
    • Careers
    • Blog
    • Events
    • Contact Us
    • Customers & Testimonials
    • FAQs
    • Site Search
  • Home
  • Feature Tour
  • Industry Types
    • Choose your industry col 1
      • Home Goods
      • Building Materials
    • Choose your industry col 2
      • Rental Industry
      • Wheels & Motors
    • Choose your industry col 3
      • Other Retailers
      • Explore All Business Types
  • Resources
    • Help Center
    • Professional Services
    • System Five Add-Ons
    • Training Events & User Conferences
    • Third-Party Integrations
    • Payment Processors
    • Maintenance Contracts
    • Shop for POS Hardware
    • Industry Partners
  • Company
    • About Us
    • Careers
    • Blog
    • Events
    • Contact Us
    • Customers & Testimonials
    • FAQs
    • Site Search

Build Your Career at Windward Software

We're always looking for people who care about solving real problems for real businesses. At Windward, you won’t get lost in layers, you’ll make a meaningful impact from day one.
 
JOIN OUR TEAM
man-and-woman-having-a-talk-in-office-2026-01-09-06-38-29-utc

Why Work at Windward?

We focus on people first — our customers, our teammates, and our communities. When you join us, you’re joining a team that supports each other, celebrates success, and works together to build software that makes a difference.

We offer competitive compensation, flexibility, and a work environment where you can grow your skills and your career. You’ll work with people who genuinely want you to succeed.

What You Can Expect

A culture built on our core values:

Take care of each other

Seek to understand and solve problems with innovation

Deliberately learn and continuously improve

See Current Positions

Copyright © 1984-2026 Windward Software Systems Inc. All Rights Reserved.

Privacy Policy