Navigating the Enterprise Evolution

Critical Enterprise CS Challenges and How to Conquer Them

Author

Tomas
March 25th, 2025

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Featured Article

We’re continuing with our series on enterprise-level growth and adaptation. And it’s about time we took a really realistic look at where you’re probably at with your customer success strategy. 

Let me take a guess…You don’t exactly have a clear CS strategy in place.

It’s ok. Enterprise CS often ends up really fragmented and confused. Too much going on, too many opportunities, not enough focus on the stuff that really matters. 

But the thing is – if you just keep sweeping those issues into the corners instead of wiping them clean, you’re gonna start getting dust bunnies.

It’s time for some hard truths. 

About where I see enterprise CS teams go wrong – and how you can do it differently.

🔥 Truth #1: Your CS is turning into a junk drawer.

Where do you put all the random things you need that don’t clearly belong anywhere else? 

Every enterprise has the odd rubber band ball looking for a home. And my guess is that your CS team is becoming the go-to dumping ground for it. 

Here’s what that might look like:

  • Major scope creep. The team is taking on tasks outside their job description.

  • Advisors to sales reps. CSMs are picking up things like upsell quotas and sales leftovers.

  • Buggy software that can’t keep up.

  • All reaction, no action. Your CSMs are fighting fires all day, and it’s not leaving much time for proactive strategic work.

So how do you fix it?

Define some damn boundaries.

  • Slash the 4-page responsibility list. If it’s not tied to customer outcomes, delegate it out.

  • Decouple CS from sales comp. Quota-carrying CSMs = conflicted priorities. Pay for adoption, not expansion.

🔥 Truth #2: You’re setting up CSMs for failure.

Sorry to break it to you. But if your CS team isn’t thriving – it’s probably not their fault.

Operational debt tends to fall onto CSMs. The symptoms:

  • Unrealistic account loads: 30–200 accounts per CSM? That’s call center math, not enterprise success.

  • Stone-age tech: “Manual menial tasks” eat 60% of their week. Where’s the automation?

  • Getting ghosted from other teams: Do your CSMs say things like ““Getting timelines from Product is like pulling teeth”? You’ve got a cross-functional breakdown happening.

If these sound familiar then it’s time to take a really hard look at your operational structure.

  • Cap accounts at 15–20 max. Any more and you’re basically turning your CSMs into transactional babysitters.

  • Automate the busywork. Could you engineer a centralized dashboard and save your people 10 hours a week? Start getting creative and build something around your unique team.

  • Force collaboration between CS and Product teams. No more “we’ll fix it next quarter.” Get them synched and supporting each other.

🔥 Truth #3: You’re measuring the wrong $#!T

“Customers don’t want a drill. They want a hole.” PMs know this phrase, but it applies here too.

Don’t make the rookie mistake of conflating activity with impact.

Stop thinking this way…

  • Outputs ≠ outcomes: 100 QBRs mean nothing if adoption flatlines.

  • Happiness ≠ success: “Happy” customers will still churn if they’re not hitting goals.

  • Features ≠ value: Adoption doesn’t automatically translate to better business outcomes.

And start thinking this way…

  • What are our track lead indicators? Think about your time-to-value ratio, ROI realization, and how your KPIs directly relate to business goals.

  • Are we building the right reputation? Customers don’t want a yes-man. Offer challenge where it adds value and honesty where it builds trust. 

🛠️ The fix is simpler than you think

If these are all sounding familiar – it’s ok. Growing pains are normal. 

And the good news is that clearing them up doesn’t mean you have to start from scratch.

Keep it focused. Keep it simple.

  1. Give your CS team clarity: Clear out the junk drawer habits and give your CSMs role descriptions and boundaries.

  2. Protect your CSMs: Keep the workload realistic, invest in automation, and strengthen cross-functional support and communication. 

  3. Outcomes > optics: If it doesn’t tie to a customer’s business goal, stop doing it. Make sure your leadership team understands this too.

Smooth out your CS team – and your customers will feel the difference. Let it all turn to chaos and they’ll feel that too.

Get real with yourself. And then set up a system that will actually turn out results.

— Tomas


P.S. Human connection isn't just nice to have—it's essential when stakes are high. The best customer service blends technology with real human empathy. I share more thoughts on balancing automation and the human touch on LinkedIn.

Tomas

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