Our People, Our Product

This is a tough business. We are selling software to business owners to help them run their entire companies effectively and efficiently. The purchase of a business management system is critical, and it represents a huge decision for the business owner. And this is where we come in.

Careers at Windward Software

Windward System Five is a fully integrated business management software designed to help businesses around the world, since 1984. Our platform is designed for retail and wholesale companies that sell, service, or rent inventory, though it's our people that make this product come to life. A career at Windward Software brings an abundance of potential, and it contributes to small business owners realizing the potential of their business, through the deployment of practical technology.

We have a diverse team of exceptional people, both at Head Office in Canada and abroad. If you would like to join our team, current opportunities are posted here: https://volarisgroup.wd3.myworkdayjobs.com/Windward

As we maintain a database of resumes for future openings, you’re invited to submit your resume and cover letter after viewing the typical position requirements below.

For all positions at Windward Software, we look for excellent customer service and communication skills, a great work ethic and a natural drive to succeed. While we prefer experience and/or knowledge in the areas of common business practices, accounting principles, inventory control, and point of sale, our in-house training program is designed to provide the training for the right individual.

We foster an environment where we work hard, but we also make sure to have some fun along the way! At Windward Software, work-life balance is important and encouraged.

Compensation and Benefits

At our corporate office in Penticton, we offer:

  • A comprehensive benefit package
  • Lakes, beaches and wineries, all in our backyard! Take your lunch break at beautiful Skaha Beach, literally just a block away
  • We have a huge staff lounge area with gym equipment, pool table and onsite showers
  • Social activities such as golf tournaments, holiday festivities, etc.

International Locations 

Penticton, BC - Canada (Headquarters)

Try out Windward Business
Management Software for yourself!

No credit card required.

Try Windward for Free

Want to know more?

Give us a Call
1 (250) 492-8888


Send Us
A Question


Book a System
Demonstration