There’s No Hill to Die On in Customer Success

Do you ever just want to scream at someone, “Get off that hill, you’re gonna hurt yourself!” Or is that just me?

That’s how I feel every time I hear someone say, “I’ll die on that hill.”

Why? Because it’s embarrassing. Truly.

The only hill I’d ever die on is the “there’s no hill to die on” hill.

I’ve built Customer Success five different times at five different companies.

Early stage, late stage, VC-backed, PE-backed, private.

SMB focus. Enterprise focus.

From $3M in ARR to nearly $100M.

And guess what? Customer Success looked different at every single one of them.

Same Discipline, Different Reality

Are there fundamentals that apply across the board? Yes.

Can you copy and paste a playbook from one company to another? No.

But every time I open LinkedIn, I see people in the comments section fighting to prove their way is the way. Trying to convince everyone else that their perspective is the correct one. That their model is the model. That their structure is the structure.

Multiple things can be true at once.

Just because something works for you doesn’t mean it will work for someone else.

And just because something didn’t work for you doesn’t mean it won’t work for someone else.

Context matters.

Company stage matters.

Product maturity matters.

Customer type matters.

Leadership philosophy matters.

Team capability matters.

Different situations call for different motions, systems, and people.

Stop Treating CS Like It’s One-Size-Fits-All

A CSM who thrives in SMB might struggle in enterprise.

An enterprise CSM might be bored out of their mind in SMB.

Maybe CSMs should own the commercial motion.

Maybe they should support it while someone else runs it.

Because… it depends.

That’s the part people don’t love to hear. There is no universal, always-right answer. There is no single structure or model that works everywhere. There is no perfect org chart that can be lifted and dropped into every company.

There are patterns.

There are principles.

There are lessons learned.

But there is no universal truth that applies to every Customer Success organization in every environment.

The Ground Is Shifting Faster Than Ever

If the rise of AI has taught us anything, it’s that things can change fast. Really fast.

Something that feels like an absolute truth today might be outdated tomorrow.

A model that worked beautifully two years ago might be inefficient now.

A role that didn’t make sense last year might be critical next year.

The pace of change alone should make all of us a little less rigid in our thinking.

Instead of planting flags and declaring hills we’re willing to die on, we should be staying curious. Testing ideas. Listening to other perspectives. Being open to the possibility that our experience is valid, but not universal.

The Best Operators Stay Flexible

The strongest Customer Success leaders I know don’t walk into a new company trying to recreate what they did before. They walk in trying to understand what this company needs now.

They ask questions before prescribing answers.

They look at data before copying structure.

They design intentionally instead of defaulting to what worked somewhere else.

They understand that success in one environment doesn’t guarantee success in another.

And they’re willing to change their minds.

So… Is There a Hill?

If there is one hill I might gently stand on, it’s this:

There’s no hill to die on.

Be open-minded.

Be receptive.

Be willing to learn from people whose experiences look different from yours.

That’s how we get better.

That’s how we evolve.

That’s how the entire discipline moves forward.

I’m curious, though.

Is there a hill you used to die on that you’ve since climbed down from?