Windward Software

Windward Software Windward Software develops integrated business management solutions to help companies grow & thrive.

Established in 1984, Windward Software's integrated business management software solutions are used by over 4,000 clients across 35 countries. At Windward, we help you run your business instead of just reporting on it!

10/28/2026

We're excited to welcome Nash Hanna to the Windward Software Systems team as our Marketing Specialist! 🎉

Nash is looking forward to exploring a brand-new space and learning from all of our great teams while making real contributions with his digital media skills. Welcome aboard, Nash!

Black Friday is a month away. The registers you have today are the registers you'll have that weekend.Before the rush, a...
10/27/2026

Black Friday is a month away. The registers you have today are the registers you'll have that weekend.

Before the rush, a quick checklist for independent retailers:

→ Are your top sellers stocked deep enough, and do you actually know which ones they are?
→ Can a new seasonal hire run a sale on day one?
→ Are your holiday prices and promos set before the doors open?
→ When it's over, how fast can you see what sold, what didn't, and what to reorder?

System Five keeps each of these at the counter, so you don't scramble to fix them in November.

See how independent retailers prep for peak season → https://hubs.li/Q04CcCZn0

Windward System Five brings big box quality software features to your business…Integrated point of sale:Ring-in sales wi...
10/26/2026

Windward System Five brings big box quality software features to your business…

Integrated point of sale:
Ring-in sales with ease as System Five allows you to scan a barcode and take payment in whatever form you and your customer want. Switching between estimates, work orders, cash or card sales and credits on the fly without re-entering a thing.

Real-time inventory control:
See what’s on hand, what’s committed to work orders and layaways, and what’s available to sell. System Five also features automated min/max levels and reorder suggestions based on sales volume and lead times to help you avoid stockouts and overstock.

Customer management (CRM):
Users can add customers mid-sale and see their full purchase history at a glance and build mailing lists from real buying behavior, such as everyone who spent more than $500 last year.

And more! All located in one platform on System Five.

Book a demo https://hubs.li/Q04Ccpmr0 to see what Windward Software can do for you and your specific business today.

That computer in the back office still works. That's the problem.When technology loses support, it keeps running, but it...
10/23/2026

That computer in the back office still works. That's the problem.

When technology loses support, it keeps running, but it stops getting security fixes. And with AI, attackers can now turn a known weakness into a working attack in hours, not weeks.

Our latest post covers:
- What "unsupported" really means for your operating systems, software and devices
- Where outdated tech hides in a typical store
- Why security is a job for your whole team, not just IT
- How System Five on Cloud takes updates, backups and monitoring off your plate

Read it here: https://hubs.li/Q04Ccn7-0

Tired of slow health billing or fixing invoice splits from scratch? Windward System Five Health Billing helps you author...
10/21/2026

Tired of slow health billing or fixing invoice splits from scratch? Windward System Five Health Billing helps you authorize full invoices in one step, correct split errors without starting over, and bill single items to multiple payees—exactly the way your funders require. Ready for efficiency at your billing desk? Reach out to see how these tools can work for your operation. Read More: https://hubs.li/Q04BZj450

10/21/2026

Welcome to, Joel Reyes, our new Sales Development Representative! 🎉

Joel is looking forward to creating long-lasting working relationships, where he can grow, sharpen his skills and contribute to Windward in an impactful way. We're excited to have you Joel!

We're hiring! ⛵Windward Software needs a Development Manager to lead Maintenance & Delivery for System Five, the softwar...
09/23/2026

We're hiring! ⛵
Windward Software needs a Development Manager to lead Maintenance & Delivery for System Five, the software independent retailers run every day.

You'll lead a team of six developers, own every production release, make the calls on tooling and upgrade paths, and help the team build and test with AI.

📍 Penticton, BC · Remote available
👉 Apply: https://hubs.li/Q04y9PdM0

Know someone who'd be great at this? Share this post with them.

09/23/2026

The wind was always in the name. Now it's in the mark.
Windward is the side the wind comes from — the side that moves you forward. Today our brand finally looks like it.
The new mark is a W drawn as a sail at full wind, with the streams that fill it. It's the signature of a company built to give independent retailers and service businesses momentum: one system, real numbers, and software that keeps up as you grow.
Fill your sails.
See the new look → https://hubs.li/Q04y9NDV0

Windward Software is committed to helping your business by providing professional services when you need them. Our profe...
05/27/2026

Windward Software is committed to helping your business by providing professional services when you need them.

Our professional services team wants to help you get the most out of your ERP - Windward System Five.

Learn more: https://hubs.li/Q04hd4yB0

Spring weekends are make-or-break moments for garden centers. When checkout lines stall, revenue walks out the door—lite...
05/25/2026

Spring weekends are make-or-break moments for garden centers. When checkout lines stall, revenue walks out the door—literally. Linebusting is one of the most effective ways garden centers protect sales during peak season by keeping customers moving quickly through checkout.

Getting customers through the checkout line quickly can mean all the difference.

Read more here: https://hubs.li/Q04hzlYq0

Address

3547 Skaha Lake Road
Penticton, BC
V2A7K2

Opening Hours

Monday 6:30am - 5pm
Tuesday 9am - 5pm
Wednesday 9am - 5pm
Thursday 9am - 5pm
Friday 9am - 5pm

Telephone

+18006635750

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