Windward System Five - 2026 Pricing, Features, Reviews & Alternatives

Windward System Five is a complete business management platform built for independent retailers, wholesalers, service businesses, equipment rental operations, and specialty stores. It brings point of sale, inventory control, purchasing, CRM, and accounting into one connected system — replacing the patchwork of disconnected tools with a single source of truth.

Most independents are running on a stack of disconnected apps: a basic POS, a separate accounting package, spreadsheets for inventory, another system for customer data. The result is duplicate entry, reconciliation headaches, and reporting that's always weeks behind reality. Windward System Five consolidates these into one integrated platform where the front counter, back office, and books share the same data in real time.

Point of Sale Ring sales quickly with a configurable POS built for real retail. Accept multiple payment types, process returns and exchanges, and manage layaways, gift cards, loyalty programs, special orders, and quotes. Multi-location stores get real-time inventory, customer history, and pricing across every store. Built-in support for serialized items, matrix products (size/color/style), kits, and assemblies handles complex catalogs without workarounds.

Inventory Control Track inventory by SKU, serial, lot, or matrix across single or multiple locations. Manage purchase orders, receiving, supplier price lists, transfers, reorder points, and physical counts. Inventory updates in real time as sales, returns, and adjustments happen — and connects directly to accounting, eliminating the reconciliation work that comes with siloed systems.

Equipment Rental For rental and mixed rental/retail operations, System Five manages rental contracts, reservations, returns, deposits, late fees, and damage charges alongside parts and service. Track every unit by serial number, location, and rental status, with support for short- and long-term contracts and recurring billing.

Liquor & Specialty Retail Liquor, wine, and beverage retailers get purpose-built tools: case breaks, mix-and-match cases, multi-pack pricing, bottle deposits, and inventory by vintage or supplier — single store or multi-location.

Accounting Run general ledger, accounts receivable, accounts payable, and bank reconciliation directly from operational activity. Every transaction posts to the books automatically — eliminating month-end cleanup and giving owners real-time visibility into profitability and cash position.

CRM & Customer Management Build repeat business with complete customer history at the counter — past purchases, preferences, special orders, account balances, and contact details. Drive loyalty programs and targeted promotions from the same data running your sales and accounting.

Windward Intelligence The built-in KPI dashboard puts the metrics that matter in front of owners and managers in real time: sales by store, staff, item, and customer; margins by category; inventory turn; dead stock; rental utilization; and customer trends. Stop waiting for end-of-month reports to find out what's happening — act on data the same day.

Configurable to Fit Your Business Independent businesses run differently from chains, and from each other. Windward System Five is highly configurable — adjust the chart of accounts, customize POS screens, set pricing rules, define user permissions, and tailor reporting to match how your business actually operates.

Personalized Onboarding, Training, and Support Every customer gets hands-on onboarding, training, and ongoing live support from a team that knows the software inside out. No ticket queues, no offshore call centers — real people who help you get the most out of the platform.

Independent retailers, wholesalers, service businesses, equipment rental operations, and specialty stores choose Windward System Five to run their operations from one trusted platform. Discover what an integrated business management system can do for yours.