When CEOs tell me they have a “product problem,” it frequently traces back to unclear decision-making. Not bad decisions. Just… ambiguous ones. Undefined ones. Slow ones. Competing ones. Here’s what it looks like inside the company: Engineers start work before alignment because decisions arrive halfway through the sprint. Roadmaps get reworked constantly because no one knows who actually owns the final call. Sales and Product escalate the same issue to different execs and get

Everyone is talking about AI. Fewer are talking about the opportunity cost of chasing it blindly. A pattern I’m seeing right now: Teams are rebuilding their roadmaps around AI because it feels mandatory — not because it solves a real customer problem. And here’s the uncomfortable truth: Adding AI features does not turn your product into an AI platform. It just means you now have more features to support. What customers actually want? Better workflows. Faster insights. Fewer c

When your company is small, staying close to customers is easy. You talk to them weekly. You know their workflows. You hear the pain firsthand. But as you scale into hundreds of customers, something happens: You lose proximity. Not because you want to — but because the math no longer works. This is the moment where many companies think they’re still customer/market-led… but the organization is actually flying blind. The solution isn’t more surveys or more one-off calls. It’s

One of the SaaS blogs I read recently made a point that’s quietly shaking the industry: the traditional SaaS exit playbook—the one where you grow to $20–50M ARR and wait for a buyer—isn’t working anymore. For years, that model was predictable. Build a solid B2B SaaS product, hit your growth targets, maintain decent unit economics, and either private equity or a strategic acquirer would show up. It was a well-understood game. That game has changed. In the first half of 2025, o

Every decently-run company tracks technical debt. Fewer track the debt that really limits growth: product debt. Product debt is what happens when features outlive their usefulness but stay anyway. When the product gets cluttered with exceptions, edge cases, and “just one more toggle” requests. It’s what happens when your product no longer reflects your strategy. The symptoms: Customers using 20% of the product but paying for 100%. Internal teams unsure which version is “right

Every CEO has been there: your biggest deal is on the line, and the prospect needs “just one feature. ”You look at the product team and say, “Can we make it happen?” They do — and it works. But a few months later, that feature becomes an orphan, your roadmap’s off track, and the product team’s sprint cadence now follows your top five accounts. You’ve crossed a subtle but dangerous line: your product team has become your sales team. This is one of the most common patterns in

The myth of product innovation is that it starts with brilliant brainstorms. In reality, your best product ideas usually start with your...

AI is everywhere in SaaS right now. But the winners won’t be the fastest to ship flashy AI features. They’ll be the ones who earn trust....

Budget season is here, and for many CEOs—especially those in private equity–backed software companies—the big question isn’t whether to...