Windward's guided path to getting more from System Five. Instead of a static list of services, everything here is organized around where your business is right now — starting out, tightening daily operations, leveling up a role, or transforming the system itself — so it's always clear what to do next.
Every business on System Five is somewhere on a journey. Answer one question and we'll show you what's next — or skip straight to the full catalog.
How do you currently manage inventory counts?
How often do your system counts not match what's actually on the shelf or lot?
Which of these sound familiar?
Select all that apply
How are reorder decisions made today?
How confident are you in your current inventory numbers?
How many locations does your business operate?
Which of these describe your invoicing or accounting today?
Select all that apply
Which of these come up for your team day to day?
Select all that apply
Any of these on the horizon for your business?
Select all that apply
In your own words, what's the one operational headache costing you the most time or money right now?
Optional
Where should we send your results?
Answer a few questions, or skip straight to the catalog, and you'll see exactly what's next — not forty services to sort through on your own.
Every stage is staffed by Windward's own Professional Services team — people who've done this hundreds of times on System Five, not a generic help desk.
Start Strong, Optimize, Master, or Transform — most businesses move through more than one stage over time, and the same program follows you the whole way.
New to System Five? Choose an implementation package or a flexible hour block to get set up right, then keep momentum going after go-live.
A monthly plan that keeps new users learning, builds good habits early, and gets your team full value from day one.
A guided rebuild of your dataset — clean customer, supplier, and inventory data imported, with history kept available for lookup.
Nobody should learn System Five by trial and error. A Windward expert gives your new team member a guided overview of the software, then goes deep on the one area…
Tighten inventory, ordering, and reporting so the system runs the way your business actually operates.
A monthly touchpoint with a Windward expert keeps System Five optimized, secure, and matched to how you work.
We review how your team actually uses System Five, find what's costing you, and show you a better way.
Beyond System Five's built-in reports, we coach you to build your own — so you see exactly where revenue comes from.
We set up barcoding your way and show your team how to scan with confidence, from receiving to checkout.
Best practices to make the right adjustments and keep your inventory value and ledger in sync.
We guide you through your sales trends and set high/low order points so the stock you need is always there.
Reconciliation techniques that catch small mistakes early, so your financial reporting is accurate when it matters most.
We put System Five's calendar to work coordinating drivers, technicians, and sales staff around your day.
We set up System Five's Fixed Assets module around your needs, so you can track value and depreciation with confidence.
A guided review of your System Five environment to uncover hidden data issues and put simple best practices in place.
Optional reports that plug into your Windward Intelligence package to reveal the patterns behind your numbers.
A focused masterclass bringing reorder points, demand, and margin together into one framework your team keeps for good.
Businesses change, and workflows set up years ago quietly stop fitting. A Windward expert reviews how your team is using System Five today, weighs it against your…
Lighting retail has its own quirks: room staging, layered invoices, tag-along kits, contractor allowances. You pick the five topics that matter most, and a System…
Role-based coaching for every seat — from the counter to the back office.
We teach your team to manage the full service side of your business in System Five, start to finish.
We coach your team on the best practices — labels, barcoding, location management — that bring real efficiency to the floor.
Front-line efficiencies at point of sale, smooth end-of-day cash-out, gift cards, and a touchscreen setup that speeds every order.
Deep command of System Five's financial tools, so your books stay clean, current, and trustworthy.
We refine your usage, streamline workflows, and improve the day-to-day experience on a system built around you.
Training fades fast without follow-through. We work alongside your team to apply the concepts from your Masterclass, tuning configurations, building workflows…
Migrations, restarts, and custom builds for businesses ready for a bigger change.
Our technical team assesses, updates, and migrates your full System Five environment, scheduled to keep impact small.
A ledger restart that gives the new owner a clean start while preserving the seller's data for history, tax, and outstanding AR/AP.
We guide your team through preparing the accounting module properly — clean trial balance, accurate AR/AP, reporting you can rely on.
Our Business Analysts assess your specific challenge — whether it's a quick efficiency win or a full custom development project — and route you to the right Specialist and the right plan.
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