Charlie Cubillas · South Florida

I make AI work in the real world.

Fifteen-plus years in enterprise sales and go-to-market — most recently as VP of Growth at an AI company, where the outbound engine I built and ran myself opened doors at Comcast, Vodafone, L'Oréal, Akamai, Redwood Bank, and Edward Jones. Now I coach small businesses and entrepreneurs to run the same playbook: AI that's set up properly, does real work, and belongs to you.

Coaching · Small businesses & entrepreneurs Builds · Agents · Automation · Websites
Charlie Cubillas
Tools I work in daily
Claude ChatGPT Kimi MiniMax
What I do

Four things, done properly.

Two people working together at a wood table with laptop and notebooks
Working sessions — your accounts, your screen
01

AI coaching

One-on-one with small business owners and entrepreneurs, in your accounts, on your real work. We set up AI around how your business actually runs — your busywork, your tools, your SOPs — and you learn by driving, not watching.

Laptop displaying a finished document on a plant-lined desk
You leave with something running
02

Courses with deliverables

Every engagement ends with one or two working tangibles: a live website, a working agent, automated social media, or lead generation. You leave with running tools you own — not homework.

See pricing →
Desktop monitor showing a live analytics dashboard on a bright desk with plants
Built, run, and maintained for you
03

Managed AI services

For businesses that want the results without becoming the expert: I build the systems, run them, and keep them maintained and improving — through my company, Cubillas Technology Group.

Tablet showing traffic and pipeline dashboards beside a coffee cup on dark wood
Outbound, follow-up, research — automated
04

Sales workflow automation

My home turf. Outbound engines, follow-up drafting, lead research, proposal and SOW generation, CRM hygiene — the same automation I've built and run in my own sales seats for a decade.

Track record

I sell for a living. The AI is how I keep up.

Data SafeguardVP, Growth

Led enterprise go-to-market at an AI data-privacy company. The tools, strategy, and workflows were mine end-to-end — an AI-driven outbound engine that booked meetings with Comcast, Vodafone, L'Oréal, Akamai, Redwood Bank, and Edward Jones.

VacoPartner · Associate Director

4× President's Club — peaked at #2 of 500+ producers. Sold and managed services for Alphabet, Netflix, TikTok, Meta, Sony PlayStation, eBay, Salesforce, and Verizon, with deals from $500K to $3M ARR.

Cre8 TeamsCo-Founder

Built a nearshore recruiting and managed-services delivery center in the Dominican Republic from zero — 50+ agents in year one, $5M+ annual revenue by year two, ISO 27001 / GDPR / CCPA-compliant delivery.

ttg · SOL DigitalVP · Director, BD

Led sales at a staffing and nearshore managed-services firm, where I built robotic process automation in Microsoft Power Automate and Power Apps — proposal and SOW generation, internal ops flows — then ran full-cycle enterprise sales at SOL Digital.

Cubillas Technology GroupFounder

My build lab and services company: a multi-agent operations platform, an LLM gateway routing local and cloud models, and websites, agents, and automations delivered to South Florida small businesses.

Hayes LocumsConsultant

Today I also run a physician-staffing desk — where AI helps me manage my workload and automates my outbound and follow-up. It's the daily proof that this stuff works when it's set up right.

Contact

Let's talk about what you're trying to build.

Whether it's your first AI setup, an automation, or figuring out where to start, I'm happy to have a straight conversation about it — no pressure, no pitch.