AI Enablement Consultancy for Founders and Operators
Real AI.
Real Operators.
Operator Intelligence is an AI enablement consultancy helping lean companies and DTC brands put AI to work through agentic digital strategy, custom AI solutions and AI training.
Most businesses know AI matters. Few know what to do about it.
The noise is deafening.
Every vendor promises AI will change everything. But for businesses built on relationships, craftsmanship, and human judgment — the path from hype to application isn't clear.
The gap is real.
Most AI pilots never make it to production. Not because the technology doesn't work — but because no one is translating it for the operators who actually run things.
That's where we come in.
Operator Intelligence was built by operators, for operators. We don't sell AI products — we build the bridge from curiosity to competitive advantage.
Three ways we put AI to work
What we do
Not hype. Implementation.
We bring AI from concept to execution for businesses built on people, relationships, and hands-on work.
Featured service
Agentic Digital Strategy
Most digital strategy dies in a deck. We build the strategy, then wire it into a multi-agent system that runs your website, SEO, paid media, email, and CRM against it every day.
Layer 1
Strategy
Human-led positioning, ICP, channel priorities, and the measurement model your growth runs on.
Layer 2
Orchestration
A multi-agent system that holds the strategy as context and watches every channel against it.
Layer 3
Channels
Website, SEO, paid media, email, and CRM instrumented with agents that act, not just report.
Built for businesses that run on people.
A few numbers behind the results we deliver
~20
Years of digital strategy
$200M+
Revenue growth Chad helped scale at Alex and Ani
$500M+
In career sales across ventures
∞
Commitment to real outcomes
Deep Knowledge, Certified.
MIT Professional Education: Applied Agentic AI for Organizational Transformation (certificate)
Our leadership holds certification from MIT's professional program — ensuring our AI strategies are grounded in current research and proven frameworks.
Anthropic AI Fluency: Framework & Foundations (course certificate)
Completed Anthropic's AI Fluency course — covering effective, efficient, ethical, and safe collaboration with AI systems. Foundational frameworks for practical AI adoption across teams and organizations.
Completed Anthropic's Teaching AI Fluency course
Course on teaching AI Fluency in instructor-led settings — for faculty, instructional designers, and teams to integrate AI literacy into training, enablement, and organizational learning programs.
The founders
Built by operators, for operators.
A partnership forged by happenstance and built on complementary expertise — technical depth meets operational mastery.
Chad Westleigh
Technical Strategy & AI Systems
15+ years at the intersection of digital strategy, data systems, and growth marketing. Helped scale Alex and Ani from $4.5M to $200M+. Led Adobe Marketing Cloud deployments across North America, APAC, and EMEA for State Street Financial. MIT Professional Education certificate in Applied Agentic AI.
Luke Freeman
Industry Operations & Growth
20+ years as an operator, entrepreneur, and investor, generating $500M+ in sales by turning complex operations into repeatable systems. Known for strong business acumen and building companies for maximum efficiency and profitability. Now focused on applying AI to automate workflows, increase revenue, and create businesses that truly scale.
ARE YOU AI READY?
Ready when you are.
Whether you're exploring AI for the first time or ready to scale what's working, take our free readiness assessment to find out where you stand — and where AI can take you.