Your First 90 Days: How to Launch a Winning AI Strategy

For many executives, the thought of launching an AI strategy feels overwhelming. The technology landscape is changing daily, the risks are real and resources are limited.

But here’s the good news: you don’t have to solve everything in one giant leap. You need a structured 90-day plan that builds alignment, minimizes risk and creates momentum.

Here’s what your first 90 days should look like:

Read: From Theory to Impact: 5 Real AI Use Cases for Mid-Size Companies

Step 1: Align at the Executive Level (Days 1-30)

AI isn’t an IT project – it’s a business initiative. That means your journey must begin with executive alignment. Without executive buy-in, AI adoption becomes scattered and siloed. With it, every project ties directly to business strategy.

What to do in the first month:

• Hold an executive workshop: Get leadership in the same room to discuss AI’s opportunities and risks. Frame the conversation around business outcomes, not only technology.
• Define priorities: Identify two or three areas where AI can make an immediate business impact, such as improving client experience, reducing costs or strengthening cybersecurity.
• Assign an executive sponsor: Every AI initiative needs someone at the leadership table who owns accountability.

Step 2: Assess Your Readiness (Days 1-45)

Before deploying AI, you must understand your starting point. Many mid-size companies discover that their biggest obstacle isn’t the technology – it’s their data. AI depends on accurate, secure and accessible data. Without readiness, AI insights are unreliable and compliance risks multiply.

What to assess:

• Data environment: Where does your data live? Is it clean, accurate and accessible?
• Cybersecurity posture: Do you have the proper protections in place to safely adopt AI?
• Current AI usage: Employees are likely experimenting with AI tools already. Audit shadow AI to understand your baseline.

Read: Does AI Help or Hurt Cybersecurity?

Step 3: Launch Pilot Projects (Days 30-60)

With alignment and readiness in place, it’s time to build momentum through small, high-impact pilots. Quick wins build momentum, executive confidence and employee buy-in. They prove that AI is about more than theory – it’s about delivering results today.

How to design a good pilot:

• Low risk, high visibility: Choose projects that won’t compromise compliance or security but will demonstrate clear business value.
• Clear ROI metrics: Define upfront how you’ll measure success, whether it’s time saved, errors reduced or client satisfaction improved.
• Cross-functional ownership: Include leaders from IT and business units to ensure adoption and accountability.

Step 4: Establish Guardrails (Days 45-75)

As pilots roll out, it’s critical to establish governance. Guardrails don’t slow down innovation – they enable it safely. Without guardrails, AI adoption can quickly become a liability. By setting boundaries early, you avoid costly compliance issues later.

What to implement:

• AI usage policies: Define what employees can and cannot do with AI tools.
• Approval processes: Require oversight before adopting new AI platforms.
• Security training: Educate employees on the risks of uploading sensitive data into public tools.

Step 5: Build Your Roadmap (Days 60-90)

By the end of 90 days, you should have alignment, readiness, a few successful pilots and guardrails in place. Now it’s time to scale. Without a roadmap, companies get stuck in pilot mode. A clear, measurable plan ensures AI becomes a sustainable driver of business success.

What to do next:

• Evaluate pilot outcomes: Which projects delivered ROI? Which need refinement?
• Prioritize initiatives: Decide which AI efforts should expand company-wide.
• Develop a long-term roadmap: Lay out your next phase of projects, tied directly to business goals.
• Communicate widely: Share wins and roadmap plans with the entire organization to build excitement and clarity.

Launch an AI Strategy with Thriveon

Your first 90 days with AI aren’t about solving everything. They’re about creating momentum so you can move from uncertainty to action. AI is here to stay. Your competitors are using it. Your employees expect it. The question is: will you lead with it, or play catch-up?

At Thriveon, we’ve guided mid-size companies in Minnesota and Florida through major technology shifts, from cloud adoption to enterprise-grade cybersecurity. That’s why our role as Fractional CIO is so critical in the first 90 days. We’ve learned that the ones who succeed don’t wait for perfection. They start small, act strategically and scale with purpose.

Request a consultation now.