Customer Success is harder than it needs to be. Not because of bad people. Not because of bad intentions. Because the profession was built on three structural failures that nobody talks about — and they've been compounding against every CS team since the beginning.
I've been in this space since before Customer Success had capital letters. I've trained tens of thousands of CSMs, worked with thousands of companies, and spent fifteen years evangelizing what CS can do for a business when it's done right.
And the whole time, these three failures have been working against us.
Structural Failure 1: The Broken Premise
Customer Success management is built around getting customers to do things they don't want to do, can't do, and even if they do them, probably won't do well enough to get the outcome they need.
Read that again.
We have built an entire profession — the operations, the org structures, the workflows, the playbooks, the QBRs, the health scores — all of it oriented around trying to get customers to take actions they have no real desire to take.
Train them. Guide them. Beg them. And then when they finally do the thing, hope they do it well enough to actually get the result they came for.
That's the broken premise. That's the foundation Customer Success is built on.
It's kind of wild when you say it out loud.
Structural Failure 2: Wrong Work With the Best People
The people I've met in Customer Success are some of the most driven, dedicated professionals I've ever encountered. Smart, empathetic, commercially aware. The kind of people any company would be lucky to have in any role.
And we have them doing administrative work.
Updating CRM fields. Preparing for calls. Writing follow-up emails. Building decks nobody reads. Documenting things that should document themselves. Pulling data from three different systems to answer a question the system should already know the answer to.
Humans are best at one thing in CS: building the relationship. Understanding what a customer actually needs. Reading between the lines. Being the trusted advisor who makes a call instead of sending an email when they sense something is wrong.
We're asking our best people to do everything except that.
Structural Failure 3: The Tools Have Boxed Us In
CS teams have been constrained by their tools since the beginning. Not because the tools are bad — most of them are genuinely good at what they do. The problem is the assumption baked into all of them.
Every CS platform comes with a worldview. A schema. A set of data structures, workflows, and operating assumptions about how CS should work. And to use the tool, you conform to that worldview.
They call it implementing best practices.
Here's the thing: every CS tool has their own set of best practices. And they're all different. Which means best practices isn't a standard. It's just their standard. And you've been bending your operation to meet it for years.
The Compounding Problem
These three failures don't exist in isolation. They compound.
The broken premise means your CSMs are spending their energy trying to get customers to do things those customers don't want to do. That's exhausting, inefficient work. The wrong work failure takes those same CSMs and piles administrative tasks on top of that already-inefficient motion. And the tool lock-in constrains both — the CSM can't even do the work the way it should be done because the tool doesn't support it.
Every week the loop runs again. The CSM is busy, constrained, and fighting against a premise that was never quite right to begin with.
Why Agentic Workflows Change Everything
Agentic workflows break all three failures at once.
The broken premise — that we need customers to do things they don't want to do — gets addressed when agents can eat that complexity. Instead of training customers to complete a technical setup step, you build an agent that does it for them. Instead of begging customers to fill out a survey before an onboarding call, you build an agent that pulls the information you need from the sources you already have.
The wrong work problem gets addressed when agents handle the administrative layer. The CRM updates itself. The call prep happens automatically. The follow-up drafts itself. Your CSMs show up to the relationship, not to the paperwork.
And the tool lock-in gets addressed because the agentic layer sits above all of your tools, not inside any of them. Your CS platform, your CRM, your product data, your call recordings — they all become nodes in a workflow you control instead of a schema you conform to.
For the first time in fifteen years of doing this, the tools fit us. Not the other way around.
That's what makes this moment different. And that's why I'm more excited about Customer Success right now than I've been in a very long time.
