“What’s Your AI Strategy?” The Most Uncomfortable Question in M&A

Over the past 18 months, there hasn’t been a single M&A conversation we’ve had where this question didn’t come up: “So… what’s your AI strategy?”

For some founders, especially those building in mature vertical SaaS categories, the question feels slightly absurd. Their business has been growing steadily for years. It’s profitable. It’s mission-critical to customers. And it has absolutely nothing to do with large language models or generative agents. So when the buyer leans in and asks about AI, the honest answer often boils down to: “We’re looking into it.”

But in today’s market, that’s not enough.

The problem isn’t that AI is a bad question. It’s that most sellers don’t have a meaningful answer. They scramble to layer in a chatbot or bolt on an AI copilot just to tick the box. Meanwhile, their engineering teams are skeptical, their customer success teams see no immediate benefit, and the AI “strategy” ends up as a slide deck footnote.

From a buyer’s perspective, this rings hollow.

What acquirers really want to hear is not that you’ve integrated ChatGPT into your help desk, but that you understand how AI will reshape your category. They’re not asking if you’re “AI-powered.” They’re asking if you’re future-proof.

We’ve seen this firsthand with founders preparing for exit. The ones who succeed don’t try to fake it. They either show a clear roadmap for how AI will unlock new capabilities, frame their niche as defensible because it’s resistant to AI disruption, or bring in new voices to shape the company’s AI thesis ahead of a sale.

Sometimes the most strategic move isn’t about launching an AI feature. It’s about rethinking how support is handled, how code is shipped, or how customers are onboarded. The value isn’t always in the tech. It’s in the operating leverage.

Buyers want to hear that you’ve thought deeply about where AI helps, where it doesn’t, and where it fundamentally changes your margin structure. That’s the real AI strategy.

Most vertical SaaS companies weren’t born AI-native. That’s fine. But today, having no point of view is a red flag. You don’t need an in-house LLM to have a credible strategy. But you do need a perspective on how your market will shift and what your customers will expect.

Because when the buyer asks again, they’re not probing for hype. They’re testing for vision.

And vision is what gets deals done.