SaasRise Mastermind Recap - Jan 14, 2026

The SaasRise Mastermind meetings on January 14, 2026, featured discussions among SaaS CEOs and founders on these topics.

There’s a risk I see over and over again in SaaS companies — especially founder-led ones — and it’s rarely talked about openly until it becomes a real problem.

There are a few moments in building a SaaS company that reliably spike a founder’s heart rate.One is when your largest customer churns unexpectedly. Another is when a core engineer quits mid-roadmap. And right up there near the top of the list is this moment:Your most important account manager or customer success manager announces they’re leaving — and they’re responsible for a massive chunk of your ARR.

This is what we discussed today in the Enterprise SaaS CEO and Founder Mastermind

Most founders assume the gap between a $3M ARR company and a $30M ARR company is product. It usually isn’t. In my experience, the real gap is the marketing system—specifically, whether you’ve figured out a repeatable way to make digital ads profitable, coordinate channels, and become impossible to ignore inside your ICP.

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