Stop playing with AI. Start using it to run your business.

We deploy secure, private commercial-grade AI agents for Chicago’s busiest founders, brokers, and agency owners. No coding required - just pure leverage.

SECURE YOUR SPOT How It Works
Deployments available in Chicagoland (In-Person) & Worldwide (Remote)

Your time is worth $500/hr.
Why are you spending it reading how-to's?

True Privacy

Unlike Cloud AI, OpenClaw runs on your hardware or private server. Your client data, emails, and innovative ideas never leave your control.

Executive Leverage

Automate email triage, calendar management, and follow-ups. It’s like hiring a Chief of Staff who works 24/7/365 for a one-time setup fee.

Chicago-Style Service

We don't just send you a link. We offer white-glove, in-person setup and training right here in Chicago. We’re real people, not a faceless SaaS.

The Difference Between "It Works" and "It's Secure".

Common deployments leave your keys exposed. We lock the doors.

Feature
Windy City Claw ✅ Windy City Claw ✅
Standard Freelancer / DIY ❌ Them ❌
Network Visibility
Invisible (Tailscale Mesh)
Exposed (Public IP / Port 22)
File System
Sandboxed (Scoped Access)
Root Access (Dangerous)
Authentication
Hardware Pairing Required
Password / Weak Auth
Vulnerability Audit
"nmap Clean" (0 Open Ports)
Multiple Attack Vectors
Currently accepting 3 new clients per month.

THE STARTER

Your first AI employee.

$1,497 One-time
  • Full remote setup (2-3 sessions)
  • Email & Calendar Integration
  • Security Hardening (Tailscale)
  • 1 Custom Workflow Automation
  • 30 Days Slack/Email Support
Best For: Solo founders and independent consultants.
BOOK STARTER SETUP
Most Popular

THE EXECUTIVE SUITE

Your AI Chief of Staff.

$2,997 One-time
  • Everything in Starter
  • In-Person (Chicago) or Remote Setup
  • Hardware Setup (Mac Mini) or VPS
  • Up to 3 Custom Automations
  • 60 Days Priority Slack Support
Best For: Real estate brokers and boutique agency owners.
BOOK EXECUTIVE SETUP

THE FULL BUILD

Your AI department.

$4,997 One-time
  • Everything in Executive Suite
  • Complete API Integrations (CRM, Lead Gen)
  • Advanced Autonomous Workflows
  • Comprehensive Team Training
  • 90 Days Dedicated Engineering Support
Best For: Established businesses needing fully custom AI automation.
APPLY FOR FULL BUILD

Optional: Ongoing "Peace of Mind" Support

Need us to stick around? Add a Managed Care plan after setup.

Care Lite

$199/mo
  • Email support (48hr response)
  • Monthly drift monitoring
  • OpenClaw version updates
  • 1 hr included support per month

Care Pro

$499/mo
  • Slack support (24hr response)
  • Weekly monitoring & proactive fixes
  • Workflow optimization
  • 3 hrs included support per month
  • Quarterly strategy call

Not sure which tier you need?

Let's figure it out in 15 minutes

How It Works

1

Book Your Slot

Choose your tier and schedule your setup sessions.

2

The Deployment

We install, secure, and configure your AI agent tailored to your workflow.

3

The Handoff

We train you on how to delegate tasks effectively.

4

Go Live

You get your time back immediately.

FAQ

Absolutely not. That's why we exist. Once we set it up, you interact with your agent just like you would an employee via email, Slack, or chat. If you can send an email, you can use Windy City Claw.

OpenClaw is designed for privacy. Unlike ChatGPT, where your data trains their models, this runs in your own private environment. The Executive Suite and Full Build include our specific "Security Hardening" protocol used by enterprise clients.

Out of the box, it can manage your calendar, draft email replies, categorize your inbox, and answer questions based on your documents. With our custom workflows (Executive Suite / Full Build), we can teach it to qualify leads, draft contracts, or summarize daily news.

ChatGPT is a chatbot. OpenClaw is an *agent*. It has access to your tools (Calendar, Email, Slack) and can *do* things, not just talk about them. It operates autonomously in the background.

All tiers come with support periods. After that, we offer optional "Managed Care" plans starting at $199/mo to keep your agent updated and running smoothly, but they are completely optional.

The Executive Suite is perfect for teams who need an AI Chief of Staff to manage communications, scheduling, and standard workflows. The Full Build is an end-to-end custom deployment, integrating deeply with your proprietary APIs, CRM, and offering significantly more dedicated engineering support to train your team.

Not necessarily. All setup tiers include an initial support period to get you running smoothly. Managed Care is for founders who don't want to think about maintenance, updates, or future optimizations ever again. It's an optional IT department for your AI.

Yes. Many clients start with The Starter or Executive Suite and upgrade their integrations or add Managed Care once they realize how much leverage they've gained.

From One Founder to Another

"Hi, I’m Dave. I’m not a massive agency. I’m a Chicago-based builder who fell in love with how OpenClaw gave me my life back. I realized that while the tech is incredible, the setup is a barrier for the people who need it most: business owners. I started Windy City Claw to bridge that gap. My goal isn't to sell you software; it's to give you leverage."