Operational Intelligence for Retail

Your business,
always on.

Software tells you what happened. Winston tells you what to do about it. Connect your tools, get a 24/7 assistant that learns your business and never stops watching.

Free to start · No credit card · 5 minutes to first insight

W
Winston
Always on
☀️ Morning Briefing — Tuesday

Yesterday: $52,340 across 2 locations (+8% vs avg)

⚠️ Blue Dream at Oakland: 14 units left — hits zero by Thursday at current pace.

👥 3 of your top 10 customers haven't visited in 18+ days. Re-engagement offer ready when you are.
7:02 AM
Yes, send the re-engagement. And reorder Blue Dream — same vendor, same qty as last time.
7:15 AM
Done. Loyalty offer sent to those 3 customers — 15% off, expires in 7 days.

Blue Dream reorder: 48 units from Emerald Farm. PO ready for your approval. 👇
7:15 AM

Connects to the tools you already use

TreezDutchieShopifySquareMetrcQuickBooksSnowflake
The Shift

The front of your business runs on software.
The back runs on Winston.

Your POS handles the sale. Your ecommerce runs the storefront. That won't change. What changes is everything behind the counter — the decisions, the monitoring, the work that falls through the cracks.

Your Software

Transactional. UI-driven. Essential.

  • 🖥️ Ringing up sales at the register
  • 🛒 Processing online orders
  • 📋 Managing manifests and transfers
  • 🌐 Running your storefront

Winston

Conversational. Proactive. Always watching.

  • 👥 "Your top 3 customers haven't visited in 2 weeks"
  • 📉 "Wednesday sales are 35% below average"
  • 📦 "Brand X drops below 20 units by Thursday"
  • 🛡️ "Compliance report due in 3 days — I've pre-filled it"
How It Works

Five minutes from sign-up to first insight.

Self-serve. No engineers. No setup calls. No integrations team.

01

Share your website

Sign in with Google or Microsoft. Drop your URL. Winston detects your business — name, industry, locations, products — in seconds.

02

Connect your tools

Toggle on your POS, compliance system, analytics, and accounting. Or start with a CSV — no commitment required.

03

Pick your channel

Slack, WhatsApp, SMS, Teams — wherever you already are. Winston meets you there.

04

Get your first insight

Winston runs a diagnostic on your data and delivers findings that change decisions — not just numbers you already know.

What Winston Does

It gets smarter every week.

You teach Winston through conversation. It builds a library of skills that compounds over time — making it harder to live without and impossible to replicate.

📊

Morning Briefings

Daily summary of sales, traffic, and anomalies — delivered to your phone before you walk in.

📦

Inventory Intelligence

Velocity-based stockout predictions, slow-mover alerts, and reorder recommendations with one-tap confirmation.

🛡️

Compliance Tracking

Deadline reminders, pre-filled reports, regulatory change alerts. Never miss a filing.

👥

Customer Intelligence

Segmentation, churn detection, and re-engagement recommendations — all from your transaction data.

🎯

Campaigns & Loyalty

AI-drafted campaigns based on behavior. Right segment, right offer, right time.

🧠

Trainable Skills

"Send me a weekend recap every Monday." "Alert my buyer when X drops below 20." Your rules. Winston remembers.

Integrations

Sees across systems that don't talk to each other.

POS + compliance + analytics + accounting in one assistant. No single platform gives you this view.

Treez Dutchie Metrc Blaze Cova Flowhub BioTrack Shopify Square Lightspeed Snowflake QuickBooks Google Analytics Google Sheets Xero

Don't see your tool? Start with a CSV upload. New connectors added monthly.

Pricing

Less than a part-time employee.
Works 24/7. Never calls in sick.

Start free. Scale with value. No contracts.

Free
$0
forever

Connect your systems and see what Winston finds — before you commit to anything.

  • Business diagnostic & website analysis
  • Daily sales summary
  • Basic inventory alerts
  • 1 messaging channel
  • 50 queries / month
  • CSV upload analysis
Get Started
Most Popular
Pro
Custom
per location / month

Your full-time operations analyst. Unlimited access, all connectors, skills you train yourself.

  • Unlimited queries & all channels
  • Full connector library
  • Morning briefings & anomaly detection
  • Customer segmentation & churn alerts
  • Compliance tracking & reminders
  • Custom trainable skills
  • Snowflake / warehouse analytics
Get Started Free →
Enterprise
Custom
volume pricing at 5+ locations

Multi-location operators. Cross-store intelligence and dedicated support.

  • Everything in Pro
  • Multi-location rollups
  • Network benchmarks & market intel
  • Custom skill development
  • Dedicated success manager
  • API access
  • Advanced model access
Talk to Us
Why Operators Stay

Winston gets better every day.
Leaving means starting over.

🧠 Accumulated Context

Winston learns your vendors, seasonal patterns, customer segments, and communication style. Months of knowledge that can't be exported.

⚙️ Custom Skills

Every behavior you teach — "send me X on Mondays," "alert Y when Z happens" — becomes a retained skill. Your library grows with usage.

🔗 Cross-Platform View

POS + accounting + compliance + analytics + loyalty in one assistant. No single vendor provides this. Removing Winston means losing the unified picture.

📈 Network Intelligence

As the network grows, anonymized benchmarks emerge. How you compare to top performers in your market. Impossible to build alone.

Stop checking dashboards.
Start running your business.

Five minutes to connect. Free to start. Smarter every day.

Get Started Free →