When 95% of AI Pilots Fail, What Can Customer Success Leaders Learn?
A recent study from MIT revealed a shocking number: 95% of generative AI pilots inside companies are failing. That means most businesses experimenting with AI aren’t seeing the results they hoped for.
But the important part is that companies aren’t giving up.
Instead, they’re moving toward a new type of system called agentic AI. Unlike the black-box models many of us worry about, these AI agents are designed to be accountable, supervised, and reliable.
And one startup, Maisa AI, just raised $25M to lead this shift.
Why This Matters for You
If you’re in Customer Success, you might be wondering: Why should I care about another AI funding announcement?
Here’s why:
Our world is moving from pilots to production.
Just like your customers expect more than “proof of concepts,” companies now expect AI to move beyond experiments into reliable, scalable solutions. If you want to see how AI is already reshaping CS roles, check out my post on AI transforming Customer Success into a strategic asset.Trust is the new differentiator.
Maisa is betting that enterprises care less about shiny demos and more about accountability, transparency, and auditability. That’s the same shift happening in Customer Success: customers don’t just want outcomes—they want outcomes they can trust. I shared a similar lesson when breaking down how to prevent $1M in churn.Process over output.
Instead of spitting out one-off answers, Maisa’s system maps out every step of the process. That’s a huge lesson for CS teams: if you want to keep executive-level buy-in, you need to show how you’re driving results, not just that results happened. I call this the backbone of executive engagement tactics.
What Customer Success Leaders Can Take Away
Move beyond hype. The AI noise is loud, but what your customers want is reliability. How can you apply the same principle in your success programs? If you’re exploring this path, my AI Customer Success Guide is a great starting point.
Build visible processes. Customers gain confidence when they can see the “chain of work” you’ve built for them. Think of your QBRs, health scores, and playbooks as your own version of AI transparency. A practical framework to do this is in my transform Quarterly Business Reviews guide.
Position yourself as a guide. As companies adopt accountable AI, they’ll need trusted advisors to help integrate it into their customer-facing operations. That’s a major opportunity for CS leaders who want to play a bigger role in digital transformation. If you want to sharpen that positioning, start with my post on getting invited into executive meetings.
Final Thoughts
The AI market is shifting—from flashy experiments to accountable systems. Maisa’s $25M raise is proof that enterprises want trust, process, and auditability.
That’s the same language we need to bring into every boardroom conversation about Customer Success.
Because in the end, whether it’s AI or CS, success isn’t about the tool—it’s about showing your work, earning trust, and delivering outcomes that scale.
👉 My take: If you’re leading a CS team today, start thinking about how to make your processes as transparent as Maisa’s “digital workers.” That’s how you protect revenue, deepen trust, and get invited into the boardroom.