How I'm leveling up my team's AI skills

Most CEOs are yelling, “Get fluent in AI or get out.”

I’m not here to dunk on that mindset. I actually agree with it.

But fear-based ultimatums don’t help anyone level up.

Here’s how I’m actually helping my team get fluent—without wasting time or burning them out:

We built an AI Fluency Ladder (Level 0–5):

• Level 0: Doesn’t use AI

• Level 1: Uses ChatGPT casually

• Level 2: Uses advanced AI tools (Gemini, Claude, deep research)

• Level 3: Builds agentic workflows (Zapier, Lindy, n8n)

• Level 4: Uses Replit to create full agents

• Level 5: Builds subagents with Cursor + Claude Code + MCPs
  → Like spinning up a team of employees, instantly

Most of our team is at Level 1.

Here’s how we’re leveling up to Level 3:

• Everyone must build one Lindy workflow in 30 days

• Record a Loom video showing it off

• Top 5–6 get featured on a live call

• Winners get Amazon gift cards ($150 / $100 / $50)

• Lindy’s even assigning CS managers to help our team when they get stuck

Next up: Replit agents.
Then: Cursor + Claude Code + MCPs.
(Yes, it’s a ramp—but it’s a deliberate one.)

If you want your team to get AI-fluent, build the culture and remove the blockers.
People don’t need more hype. They need a system that works.

To helping your team scale with AI,
Eric Siu

P.S.

1 - We’re hiring AI-forward performance ad creative strategists, AI-forward SEOs and paid media people, AI short form creators, AI automation interns, and more.. If you’re interested, apply at our Careers page.
2 - We launched ClickFlow to help automate and scale SEO. We’re giving away 25,000 words for free - sign up for the waitlist at the link.
3 - Interested in creating 1:1 personalized LinkedIn ads in minutes instead of weeks? Sign up for the Karrot.ai waitlist.
4 - If you want to grow faster using the power of AI, my agency Single Grain is offering free marketing plans to Leveling Up newsletter subscribers, check it out here.
5 - For more in-depth marketing content, check out my Leveling Up YouTube channel
6 - To help this newsletter improve, fill out this survey
7 - Constant Contact is offering Leveling Up subscribers a free 30 day trial. If you’re interested in an all-in-one platform to manage marketing campaigns across email, text, social, and more check it out at the link.