I spoke to 40+ CSMs and CS Executives: Here Is What I Learned
P.S. I’ve included below 3 ways that Jesse Itzler (founder of Marquis Jet, later acquired by NetJets) built lasting customer relationships
Over the past year, I’ve had 40+ conversations with customer success leaders across the SaaS industry. Some were heads of CS at mid-market & enterprise companies. Others were frontline CSMs juggling hundreds of accounts. Despite the range of roles and company sizes, the same theme kept resurfacing:
Even with all the data, tools, and tech we have today, most CSMs are still a step behind churn. They're reactive not proactive.
Most of these teams aren’t lacking information. In fact, nearly everyone I spoke with said they already have the data—product usage, support activity, stakeholder sentiment. But it’s scattered across three or more platforms, buried in dashboards, or surfaced too late to act on. It’s not that they don’t know what’s happening—it’s that they don’t know in time. Patterns get missed. Risk signals go unseen. And by the time someone realizes a customer is drifting, it’s already too late.
Even when CSMs do catch signs of risk, the next steps often aren’t clear. Most tools can show you a health score or flag sentiment changes—but they rarely tell you why. Is the risk being driven by a dip in usage? A backlog of support tickets? A missed QBR? Knowing who’s at risk is easy. Understanding what’s driving that risk—and what to do about it—is what really matters.
And it’s not for lack of effort. CSMs are overextended. The average rep I spoke to manages between 75 and 200 accounts. That’s a staggering load—especially with the amount of fragmented data, limited automation, and growing pressure to hit retention and expansion goals. These aren't reps dropping the ball—they're doing everything they can in a system that’s set up to keep them reactive.
The kicker? Most teams aren’t asking for more dashboards. In fact, some of the most seasoned leaders told me they’re overwhelmed by dashboards. What they need isn’t more noise. It’s clarity. It’s precision. It’s insight delivered into the flow of work—not tucked away behind a half dozen sub-pages. They want better decisions—not more raw data.
Three Uncommon Ways to Deepen Customer Relationships (That Actually Work)
One of the best pieces of advice I’ve heard about retention came from Jesse Itzler, the entrepreneur behind Marquis Jet. He’s obsessive about customer relationships—and built a multimillion-dollar business largely by treating people better than anyone else in his space. His strategies aren’t flashy or expensive—but they work.
1. Handwritten Letters
“Handwritten letters break through the clutter.” Sometimes it’s hard to get through assistants or stay at the top of a champion’s inbox. Everybody reads a handwritten letter. Make it a point to write 10 a day—over the course of a year, that’s more than 3,000 personal, memorable touch points you’ve had with customers.
Be the letter guy.
2. Compliment, Congratulate, and Console
“Business can be transactional, but relationships can’t.”
When you build deep, meaningful relationships with your customers, you reap the benefits in the moments that really matter.
Here’s an example:
“Jimmy, it’s Jesse. I heard your son got into Duke University. If my kids got into Duke, I’d be on cloud nine. I’m on cloud nine for you, your son, and your whole family.”
Authentically compliment, congratulate, or console them on something that genuinely matters to them. Especially when no one else is doing it… they’ll never forget it.
3. Do the Unexpected
While everyone in your industry plays a nine-inning game, you play ten. Do things no one expects. Everyone expects you to return emails and follow up after meetings. Take it a step further. Send a personal note after a small win. Show up when it’s not about business. Surprise them with genuine thoughtfulness. That’s what builds long-term trust.
Final Thought
Reducing churn starts with better systems and smarter data—but long-term retention lives in relationships. Insight and automation can help you see who’s slipping, but how you show up after that is what sets you apart.
Write the letter. Make the unexpected call. Celebrate something no one else noticed.
That’s how loyalty is built—quietly, consistently, and personally.