About Operator Intelligence
Some partnerships are engineered. This one wasn't.
Quick facts
- Founded
- 2026
- Founders
- Chad Westleigh, Luke Freeman
- Legal name
- Operator Intelligence, LLC
- Based in
- Brentwood, Tennessee
- Offerings
- Agentic Digital Strategy, AI Enablement & Custom Solutions, AI Training & Fluency
- Who we serve
- founders, operators and leadership teams at lean companies (typically $1M–$10M in revenue), DTC brands and select Fortune 1000 teams
- How we work
- a two-week AI readiness assessment, then quick-win pilots in four to six weeks
- Proof
- four case studies
Chad Westleigh and Luke Freeman met by happenstance on vacation in Mexico nearly a decade ago — two entrepreneurs, their wives, and a week of sun and music that had no business producing a business. But somewhere between the conversations about life, building things, and the relentless pull of entrepreneurship, a genuine friendship took root.
They stayed in touch. They kept talking. And the way serious operators tend to do, the conversations kept drifting toward what was next.
Chad Westleigh
Technical Strategy & AI Systems
Chad has spent nearly 20 years at the intersection of digital strategy, data systems, and growth marketing. He was among the original hires at Alex and Ani, joining early and helping build the digital strategy and marketing ecosystem that carried the brand from $4.5 million to $200M+ in revenue between 2010 and 2013 — one of the most dramatic DTC growth stories of the new millennium.
He went on to work with early-stage and hyper-growth brands, and led enterprise-scale deployments including the Adobe Marketing Cloud implementation across North America, APAC, and EMEA for State Street Financial.
He has mentored emerging companies through the NYFTL, spoken internationally on marketing intelligence and strategy, and spent the last two years in applied AI work — designing and deploying AI-powered systems and workflows for brands across industries. He holds an MIT Professional Education certificate in Applied Agentic AI for Organizational Transformation.
Read Chad Westleigh's full profile →
Luke Freeman
Industry Operations & Growth
Luke Freeman is a seasoned entrepreneur, operator, and advisor with over 20 years of experience building and scaling businesses across diverse industries. He has generated more than $500 million in career sales by transforming complex operations into efficient, repeatable systems that drive sustainable growth.
As Founder & CEO of Wizard, Luke has worked with Fortune 500 companies, professional sports teams, major universities, and multi-location brands to develop scalable solutions across product development, branding, and operational execution.
His background includes investments and hands-on experience in consumer products, influencer marketing, live events, cannabis, real estate, and ready-to-drink beverages. In addition to building his own brands, he has coached dozens of entrepreneurs, helping them optimize operations, unlock new revenue opportunities, and build businesses positioned for long-term success or exit.
Through Operator Intelligence, Luke now helps companies leverage AI-driven systems and automation to reduce costs, increase efficiency, and create scalable infrastructure for growth.
Read Luke Freeman's full profile →The spark that became Operator Intelligence.
On a recent call — the kind of catch-up these two have had dozens of times — Chad was talking through the AI work he'd been doing: building real systems, real workflows, real outcomes for brands willing to take it seriously. Not experimentation. Execution.
Luke, who has always had an antenna for where industries are moving before most people see it, was hearing the same question everywhere in his network: How do we actually do this? Not the hype. The application. The implementation. The honest answer to what AI is worth to a real business run by real people.
The gap between that question and a credible answer was obvious. So was the solution.
That's Operator Intelligence
Built for the people actually running businesses.
Chad brings the technical depth, the systems thinking, and the track record of building infrastructure that scales. Luke brings the industry knowledge, the network, and the platform of someone people trust to tell them the truth about what's coming.
Together, they're not pitching a product — they're solving a problem they've each watched compound for years. For the founders, executives, and operators who don't need more noise about AI, but do need a proven path from curiosity to competitive advantage.
Ready to talk about your business?
Tell us where the manual work piles up. We'll show you where AI fits first.
Book a call