Windward Software
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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!
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
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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
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
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
Transform your business with Windward Software! Our comprehensive solutions are designed to streamline operations, enhance customer experiences, and boost your bottom line. Whether you're in retail, wholesale, or service industries, Windward Software has the tools you need to succeed. Discover the power of efficient business management today!
Book your free demo today: https://hubs.li/Q04hdbB90
05/14/2026
Expanding into multiple retail locations is a major milestone—but it also introduces a new level of complexity. Without the right systems in place, managing inventory across stores can quickly become inefficient, error-prone, and costly.
Inventory control software for multiple locations gives retailers real-time visibility into stock levels, product movement, and availability—across every store, warehouse, and backroom.
Learn more: https://hubs.li/Q04g5YlF0
05/12/2026
Floor planning is a special type of financing offered by lenders. Retail floor planning allows dealers the flexibility to offer the right product mix for customers to choose from. For example, dealerships for automobiles, recreational vehicles, and boats, as well as home goods retailers will turn to floor plan loans to purchase inventory.
Read more: https://hubs.li/Q04g5vw80
When your business runs on disconnected systems, it’s easy for things to slip—double entry, missed details, and reporting that’s always a step behind. The fix isn’t another patchwork tool. It’s an integrated solution that keeps everything connected, so your team can move faster and make decisions with confidence.
That’s exactly what Windward System Five is built for: a single hub where POS, inventory control, purchasing/fulfillment, accounts receivable, and e-commerce/cataloging all work together. You can spend less time reconciling systems and more time running the business.
If you’re ready for simpler workflows and clearer visibility, let’s talk: https://hubs.li/Q04flF-H0
05/06/2026
We’re hiring!
We’re looking for an Intermediate Sales Development Representative (SDR) to help drive new business and connect with prospective customers across our target industries.
This is a great opportunity for someone who enjoys meaningful sales conversations, modern prospecting, and using AI-powered tools to work smarter—not just harder.
If you’re confident in your ability to identify and qualify opportunities, collaborate with marketing and sales, and create real value in early-stage conversations, we’d love to hear from you.
📍 Remote (Canada)
💼 Full-time
Apply here: https://hubs.li/Q04fF99_0
04/23/2026
📣 We’re hiring! Windward Software is looking for a Summer Marketing Intern (Fixed Term) to join our team.
If you’re a self-starter who wants real, hands-on B2B marketing experience (not just “shadowing”), this role gives you the chance to contribute to meaningful projects across market & competitive research, content creation, digital publishing, and marketing operations.
In this internship, you’ll support initiatives like:
✅ Researching markets and competitors to inform campaigns
✅ Helping draft and develop marketing content and assets (blog/email/social + collateral support)
✅ Supporting digital publishing and marketing workflows using modern tools like HubSpot, Canva, and AI-assisted content tools
What you’ll gain: exposure to real campaigns, practical experience with content publishing/marketing operations and portfolio-ready work you can actually share (where appropriate).
📍 Location: Remote within Canada
🗓️ Term: Summer (fixed term)
Interested?
👉 Apply here: https://hubs.li/Q04dh10C0
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Contact the business
Telephone
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 |
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