What Windward Software Systems Inc. does

Windward Software Systems Inc., founded in 1984 and headquartered in Penticton, British Columbia, develops Windward System Five, an integrated ERP and point-of-sale platform purpose-built for small and mid-sized retailers, rental operators, and service businesses. The platform unifies POS, inventory control, accounting, CRM, multi-store management, franchise operations, and reporting in a single codebase, available as both an installed deployment and a cloud-hosted offering on Microsoft Azure with feature parity. The product portfolio includes more than ten add-on modules covering advanced inventory (zone/aisle/shelf/bin tracking), rentals, multi-currency, multi-department, payroll, health billing (ADP AADL), opportunity tracking, and business intelligence, alongside a growing integration ecosystem connecting Windward to WooCommerce, WebSell, AVB LINQ, XO Logic, Lights America, Orgill, Liquor Connect, MultiCat, Ship Rush, Microsoft Power BI, and multiple payment processors. Windward serves 4,000+ clients across 35 countries in verticals including appliance and home goods, building materials, garden centers, lighting showrooms, liquor retail, auto parts, powersports, and equipment rental, with named customers such as Green's BrandSource, Windsor Plywood, Northwest TIM-BRMart, and Broadway Wine and Spirits. The company distributes through a direct sales-led motion combined with flagship channel partnerships as Gold Provider for BrandSource (US) and MEGA Group (Canada) dealer networks, supplemented by professional services, the Windward Learning Academy training platform, and recurring integration fees. Revenue derives primarily from subscriptions (cloud and maintenance), separately priced add-on modules and integration services with annual recurring fees, and project-based professional services; the company is privately held and operates as a subsidiary of Volaris Group, itself an operating group of Constellation Software Inc.

Name

Windward Software Systems Inc.

Legal name

Windward Software Systems Inc.

Website

https://windwardsoftware.com

Company type

Private

Founded year

1984

Operating status

Operating

Headcount range

101–250 employees

Short description

Windward Software Systems Inc., founded 1984 in Penticton, Canada, provides Windward System Five, an integrated ERP, POS, and inventory platform for 4,000+ SMB retailers, rental operators, and service businesses across 35 countries, distributed via direct sales and BrandSource/MEGA Group dealer channels under Volaris Group ownership.

Ownership category

akta.pro rank

Headquarters

HQ city

Penticton

HQ country

Canada

HQ region

North America

Offices2 records

Markets served

GTM type

B2B

Offering type

Software

Cost components

Personnel, Technology or R&D, Marketing or Sales, Operations

Revenue model

1. Software Subscriptions (Cloud): Windward System Five on Cloud is a subscription-based SaaS model deployed on Microsoft Azure, providing virtual desktop access with lower upfront costs and managed server infrastructure.
2. Add-On Modules: Additional modules including Advanced Inventory Control, Rental Solution, Multi-currency, Departments, Contractor Solution, Health Billing, Payroll, Opportunity Tracking, Windward Intelligence, and Windward SCAN App are priced separately.
3. Integration Services: Third-party integrations with payment processors, Microsoft Power BI, WebSell, WooCommerce, AVB LINQ, Ship Rush, Lights America, XO Logic, Orgill, Liquor Connect, and MultiCat are available as add-on services.
4. Professional Services: Implementation services, training, technical packages (data restart, server migrations, ledger restart, data loads), and role-based packages provided by Windward's professional services team. Plans start at $750.
5. Integration Setup and Maintenance: XO Logic integration: $2,000 setup + $348/yr (cloud) or $626/yr (installed). Lights America integration: $2,000 setup + $948/yr.

Pricing tiers

Go-to-market motion2 records

Distribution channels4 records

Marketing channels8 records

Core offering

Windward Software Systems Inc. develops and sells Windward System Five, an integrated ERP and point-of-sale (POS) software platform for small and mid-sized retailers. The platform combines POS, accounting, inventory control, customer relationship management, and eCommerce into a single solution deployed either on-premise or in the cloud via Microsoft Azure, and is supported by more than 400 add-ons and integrations.

Product overview

Windward Software Systems Inc. offers Windward System Five as a unified ERP and business management platform for SMBs, combining integrated POS, accounting, inventory control, and CRM functionality. The core platform is available in two deployment options: the traditional installed version and the cloud-hosted Windward System Five on Cloud (built on Microsoft Azure). The product ecosystem includes multiple add-on modules such as Advanced Inventory Control (AIC) for warehouse zone/aisle/shelf/bin tracking, Department Solution for multi-location businesses, Rental Solution for equipment rental management, Multi-Currency for international transactions, Health Billing (ADP AADL), Payroll, Opportunity Tracking, and Additional Set of Books. E-commerce capabilities are provided through integrations including Windward Connector for WooCommerce, WebSell, AVB LINQ, XO Logic, and Lights America. Business intelligence is enhanced via Windward Intelligence and Microsoft Power BI integration. The company also provides Professional Services for implementation, training, and ongoing support through the Windward Learning Academy.

Differentiator

Problem solved

Functional benefit

Brands

• Windward System Five: All-in-one ERP and business management software with integrated POS, accounting, and inventory control for retail, rental, and service businesses.
• Windward System Five on Cloud
• WebSell
• Windward Intelligence
• Windward Learning Academy
• System Five Sidekick

Products and services

• Windward System Five Flagship integrated ERP and point-of-sale platform that combines POS, accounting, inventory control, customer management, and back-office functionality for small and mid-sized retailers across multiple specialty verticals.
• Windward System Five on Cloud Cloud-hosted edition of Windward System Five delivered on Microsoft Azure, providing the same integrated ERP and POS functionality as the on-premise version without requiring local servers or manual updates.
• Advanced Inventory Control Add-on module that extends System Five with advanced inventory management capabilities including lot, serial, and assembly tracking beyond the core inventory functionality.
• Rental Solution Add-on module for managing equipment and merchandise rentals, including rental contracts, deposits, availability tracking, and rental-specific pricing.
• Department Solution Add-on module that introduces departmental hierarchy and segmentation inside Windward System Five, allowing retailers to organize and report on operations by department.
• Multi-Currency Add-on module that enables Windward System Five to process and report transactions in multiple currencies for retailers operating across borders.
• Health Billing (ADP AADL) Add-on module that supports Alberta Aids to Daily Living (AADL) health-product billing and claim processing for pharmacies and health-product retailers using Windward System Five.
• Payroll Add-on module providing integrated payroll processing, deductions, tax handling, and reporting inside Windward System Five.
• Opportunity Tracking Add-on module providing CRM-style sales pipeline management and opportunity tracking inside Windward System Five for sales-driven retailers.
• Additional Set of Books Add-on module that allows retailers to maintain additional sets of accounting books within Windward System Five for separate entities, divisions, or reporting structures.
• Windward Intelligence Business-intelligence add-on for Windward System Five that provides dashboards, analytics, and reporting on retail, sales, and operational data.
• System Five Sidekick Companion mobile application that provides on-the-go access to Windward System Five data including inventory lookups, customer information, and reports from a smartphone or tablet.
• WebSell E-commerce Solution E-commerce solution for Windward System Five that syncs online storefronts with the back-office system for inventory, pricing, and customer data.
• Windward Learning Academy Training and certification program for Windward customers, partners, and employees covering the configuration and use of Windward System Five.
• Professional Services Consultative implementation, training, data migration, and customization services delivered alongside Windward System Five to onboard and configure retailers.

Quantifiable outcome

• Trusted by thousands of clients worldwide since 1984
• +1 more outcomes

Named customers13 records

Segments7 records

Ideal customer profiles6 records

Technology focussed Yes

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Integration11 records

Feature14 records

Partnerships

Seven partnerships are on record, tiered flagship and core.

• BrandSource (US)flagshipChannel Partner/ Reseller/ DistributorWindward Software is a Gold Provider Platform for BrandSource US, serving home goods retailers within the BrandSource dealer network with integrated POS and business management solutions.
• MEGA Group (Canada)flagshipChannel Partner/ Reseller/ DistributorWindward Software is a Gold Provider Platform for MEGA Group in Canada, serving home goods retailers within the MEGA Group dealer network.
• AVB LINQcoreTechnology or IntegrationAVB LINQ integration enables BrandSource members to sync catalogs, publish quantities, and fulfill orders from AVB websites directly within Windward System Five.
• WooCommercecoreTechnology or IntegrationWindward Connector for WooCommerce allows retailers to publish inventory to WooCommerce sites and retrieve sales for fulfillment using System Five. Syncs part numbers, descriptions, prices, quantities, and images.
• XO LogiccoreTechnology or IntegrationXO Logic integration syncs customer and product details, downloads orders as estimates/work orders, and provides full product catalog synchronization for lighting showrooms. Pricing: $2,000 setup + $348/yr (cloud) or $626/yr (installed).
• Lights AmericacoreTechnology or IntegrationLights America integration syncs product details, images, and stock levels between Lighting showrooms' websites and Windward System Five. Enables wish list downloads and quick sales. Pricing: $2,000 setup + $948/yr.
• Payment Processors (Multiple Vendors)coreTechnology or IntegrationWindward System Five integrates with multiple payment processors for credit/debit card processing, gift cards, and contactless payments including EMV and tap payments up to $150.

Scale indicators5 records

Recent moves6 records

Expansion highlights6 records

Direct peers

• Lightspeed Commerce: Lightspeed provides cloud-based POS and commerce platforms for retail, restaurant, and golf SMBs globally. It is a direct peer to Windward in retail POS, serving multi-location independent retailers with an integrated POS + eCommerce + payments stack.
• Shopify POS: Shopify's POS offering targets small and mid-market retail and pop-up merchants with integrated payments, inventory, and online store sync. It is a direct peer to Windward's System Five platform for SMB retailers that need omnichannel POS plus back-office.
• Square (Block, Inc.): Square provides integrated POS, payments, and business management software to SMBs across retail and service verticals. It is a direct competitor to Windward in serving small retailers with mobile-first, subscription-priced POS and inventory tooling.
• LS Retail: LS Retail builds POS and ERP software for retail, hospitality, and franchises, layered on Microsoft Dynamics. It overlaps Windward directly in retail and franchise management software for SMB and mid-market chains.
• Revel Systems: Revel Systems provides iPad-based POS and business management software for retail, restaurant, and grocery SMBs. It is a direct peer to Windward in integrated POS plus back-office for multi-location SMB retailers.

Emerging players

• Cin7: Cin7 delivers cloud inventory management and POS-adjacent software for product sellers, with strong integrations to multiple sales channels. It overlaps Windward's inventory control and multi-channel commerce capabilities for SMB and mid-market retailers.

Broad incumbents

• Epicor Software: Epicor offers ERP, retail, and distribution software aimed at mid-market manufacturers and retailers. It is a broad incumbent that competes with Windward in retail ERP, particularly for building materials and lumber dealers.
• Microsoft Dynamics 365 Business Central: Microsoft's cloud ERP for SMBs competes with Windward System Five as an integrated back-office platform. Windward itself hosts on Azure and integrates with Power BI, making Dynamics a partner-adjacent and overlap competitor.
• QuickBooks Point of Sale / Intuit: Intuit's QuickBooks ecosystem dominates SMB accounting and increasingly offers POS and payments add-ons. Windward customers (e.g., Broadway Wine and Spirits) explicitly displace QuickBooks AP, making Intuit a frequent incumbent competitor.
• Oracle NetSuite: NetSuite is a cloud ERP platform serving SMB and mid-market companies with financials, inventory, and CRM. It represents the upper-end incumbent alternative for SMB retailers that outgrow Windward System Five.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat5 records

Key risks6 records

Key highlights7 records

Customer concentration

• LinkedInlinkedin.com/company/windward-software
• Xx.com/windwardsystem5
• Facebookfacebook.com/windwardsoftware

Compliance4 records

Revenue estimate

Valuation estimate

Number of profiles

Profiles4 records

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Windward Software Systems Inc.