AI Strategy · Implementation · Enablement

Your company knows AI matters.
You just don't have anyone leading the charge.

The Orlando Group embeds as your fractional Chief AI Officer — bringing the strategy, implementation, and team enablement that turns AI from a buzzword into a competitive advantage.

Schedule a Conversation How it works ↓
Track Record
ClincChief of Staff · $0 → $15M ARR
Kore.aiDir. Product Marketing · $20M → $100M ARR
AmeliaVP Marketing · Nine-figure acquisition
University of MichiganB.S. Computer Science
What We Deliver

Three pillars. One engagement.
Your AI transformation, handled.

01 — Strategy

AI Roadmap & Competitive Intelligence

Monthly executive briefings on how AI is reshaping your industry. Competitor analysis. A clear, prioritized roadmap so you're making moves — not guessing.

02 — Implementation

Workflow Automation & Tool Builds

We identify your highest-ROI processes and automate them — CEO dashboards, CRM integrations, AI agents for lead qualification, reporting, and operations. Real systems, not slide decks.

03 — Enablement

Team Training & Capability Building

Hands-on sessions that make your entire team more productive with AI. We don't just build for you — we teach your people to build for themselves.

Who This Is For

Built for companies doing $5M–$50M+
that want to lead in the AI era.

You know AI matters

Every conference, every competitor, every board meeting is bringing it up. But nobody on your team is leading the charge.

Your team uses ChatGPT for emails

That's where 95% of companies stop. The gap between that and what's actually possible is where the competitive advantage lives.

You're hiring when you could be automating

That $10-20K/month role you're about to fill? There's a good chance an AI system can handle it for a fraction of the cost.

You want to lead in the AI era

our tech team is focused on product and engineering. You need someone dedicated to embedding AI across operations, GTM, and the rest of the business.

About

This isn't a side project.
It's a decade of enterprise AI, applied.

Nick Orlando

Nick Orlando has spent 8+ years inside the companies building enterprise AI — scaling startups from zero to nine-figure outcomes. He's led go-to-market, product, and growth at three of the most recognized names in conversational AI and intelligent automation.

The Orlando Group brings that operational depth to growth-stage companies that need AI leadership without the overhead of a full-time executive hire. We don't just advise — we build, implement, and train your team to operate at a fundamentally higher level.

Based in Metro Detroit. Working with companies worldwide.

8+
Years in enterprise AI
3
AI companies scaled
$100M+
ARR growth driven
9-fig
Exit experience
Get Started

Let's find where AI moves the needle
in your business.

No pitch. No pressure. A focused conversation to understand your operations and show you what's possible.

Schedule a Conversation