Your CEO Says “We Need AI.” Start Here

Ep 15: Your CEO Says “We Need AI.” Start Here

Your CEO walks into a meeting and says, “We need AI.” That is the whole brief.

Do you hire an AI engineer? Buy ChatGPT or Claude for the team? Ask your developers to build an agent? Or start somewhere else?

Episode 15 introduces Dear Human in the Loop, our advice series for builders and decision-makers. Oscar Gallo and Matt Wozniak answer four questions they keep hearing from founders, clients, developers, and engineering leaders.

1. Where should a company start with AI?

Start with the work. Map a process your team understands. Find one repetitive task that costs time or creates delays. Test a small change and measure the result.

If your company already pays for Google Workspace or Microsoft 365, begin with the AI tools inside software your team knows. Work on a copy of the document or spreadsheet. Give clear instructions. Check every result.

Takeaway: Start with problems, not prompts.

2. Should your first technical hire be an AI engineer?

Usually, no. An early startup needs someone who can solve the main business problem, move across the product, and learn fast. Product-market fit matters more than model selection.

The exceptions are companies where AI research, model development, or robotics is the product.

Takeaway: Hire for the problem, not the job title everyone is discussing.

3. What if your developers resist AI?

Ask why. Security, privacy, compliance, and code quality are valid concerns. Put controls in place. Then show one useful example on a real task.

Do not measure prompts or force tool use. Give the team time to learn. Improve tickets, acceptance criteria, tests, reviews, and quality gates so both people and agents get better instructions.

Takeaway: Trust beats mandates.

4. Which skills will matter five years from now?

Software engineering fundamentals. System design. Architecture. Product thinking. Communication. Critical thinking. Adaptability.

Specific prompt tricks and model quirks will expire. Your ability to understand a system, explain a decision, review generated code, and reject a bad answer will keep its value.

Takeaway: Learn principles. Tools will change.

Your hosts

• Oscar Gallo: AI Engineer and entrepreneur. I live in the intersection of engineering and businesses.
• Matt Wozniak: Serial Builder and relentless executor. I come from the lens of what works and what doesn't.

Listen now

• Watch on YouTube
• Listen on Spotify

Have a question for a future episode? Send it to Human In the Loop.