Earlier this week, I spent time in San Francisco with customer success and post sales leaders from across the ecosystem. Conversations at events like these are useful because patterns surface quickly. Different companies. Different stages. Same problems.
At the same time, over the last few months, I have been thinking deeply about why customer success feels harder than it should for so many teams. So, when I presented some of my thoughts at the event, they resonated deeply with the attendees.
Headcount stays flat while expectations rise. Leaders assumed AI will absorb the load. The best CSMs are stretched thin, carrying accounts and context in their heads. Escalations become the default operating model. Dashboards increase, but decisions slow down.
They are system problems.
Customer success breaks when it is treated as a team that reacts, rather than a system that operates. Hero CSMs become single points of failure. Knowledge stays trapped with individuals. Every edge case requires a manager. Alignment meetings replace ownership. The organization stays busy but outcomes do not improve.
What actually scales customer success is much simpler, and much harder.
Clear signals that demand action instead of noise. Defined decision rights so trade-offs happen fast and at the right level. Repeatable motions tied to lifecycle moments, not individual style. Incentives that reward the behaviors you want, not the activity you can measure.
These are operating choices. Tools come later.
AI deployment is a good example of this. It does not fix customer success. It amplifies whatever structure already exists. A broken system with AI just creates faster chaos. A designed system creates leverage.
If you are leading customer success or post sales today, the real work is not hiring harder or buying better software. It is stepping back and designing the system your team operates in. When the system works, people can do their best work. When it does not, no amount of heroics will save you.
For those interested, I am sharing the presentation that I made for the event.
Customer Success is a System, Not a Team (Expand, San Francisco)
System perspective vital. AI impact needs thoughtful framing.