The Journey: #49 White Gloves Get Dirty

When I started as a CSM back in 2012, I was convinced I had the best job on the planet.

Enterprise accounts. Fortune 500 logos. Big budgets. Big expectations. A whole lot of white glove energy.

And I took that “white glove” part very literally.

I met with my customers weekly or bi-weekly. I ran every call. I coordinated every conversation. If they had feedback for Product, I was the messenger. If they escalated a ticket, I was the firefighter. If they were speaking at our customer event, guess who was front row?

Spoiler: It was me. It was always me.

I actually believed my customers were my customers.

I made sure anyone who needed access went through me. I personalized everything. Every template was rewritten. Every email was tailored. Every experience was bespoke.

I wore those white gloves with pride.

I obsessed over creating the perfect experience, building airtight relationships, and showing up like the world’s most dedicated consultant. In my mind, this was the only way to serve customers of this size and with this level of investment.

And honestly… for a while, it worked.

But then something happened.

I had to scale.

Not in theory. Not in a “someday” way. In a real “there aren’t enough hours in the day, and my calendar is a dumpster fire” way.

The thought of introducing automation and digital experiences terrified me.

What if an email went to the wrong person?

What if a playbook triggered at the wrong time?

What if something broke and I didn’t know?

I kept telling myself it wasn’t worth the risk.

But the truth?

It wasn’t the risk. It was the fear.

Fast forward a few years…

I go from IC to leader and find out the hard way that scaling isn’t optional. It’s not a nice-to-have. It’s a lifeline. It’s a business requirement.

And here’s the twist I never expected: Done right, digital doesn’t dilute the customer experience, it elevates it.

So I rolled up my sleeves and got to work.

Here’s what I did to rebuild the customer journey for scale:

• Redesigned the entire customer journey across segments with a digital-first strategy

Not digital-only. Digital-first. Human where it matters most.

• Layered in human capital only where it added value

We used RACI to define who actually needed to be involved and when.

• Audited the entire tech stack

What did we have? What was duplicative? What was missing? What needed replacing?

• Defined the KPIs that mattered

And ensured we had the systems to measure and manage them without guesswork.

• Built the internal change management plan

Including restructuring the team. Brutal work, but necessary work.

• Communicated the changes to customers

Reset expectations. Explained the “why.” Kept trust intact.

And after doing this a few times across different companies, I learned to look for very predictable red flags that told me it was time to evolve from white glove to hybrid.

Here are the 5 red flags leaders ignore at their own risk:

1. Your CSMs spend more time coordinating than consulting

If they’re acting as project managers instead of strategic advisors, your model is already cracking.

2. Your customers don’t know who to go to for what

If every request funnels to the CSM, congratulations, you are the bottleneck.

3. You can’t measure success consistently across accounts

If every CSM has a different process, template, and workflow, you don’t have a customer journey. You have organized chaos.

4. Your onboarding experience collapses under volume

If adding 5 more customers feels like adding 50, your model isn’t scalable.

5. Your leadership team “hopes” things are happening

If you need to rely on anecdotes instead of data, it’s time to digitize.

The takeaway?

White glove service is not the problem.

The belief that only humans can deliver white glove service is the problem.

Your white gloves will still get dirty.

But scaling the journey ensures they stay intact.

If you want customers to feel supported, guided, informed, and valued, the answer isn’t “more humans everywhere.”

It’s putting humans where they matter most, and letting digital carry the rest.

That’s how you deliver world-class experiences at scale. That’s how you build a business that can grow without breaking. That’s how you move from “my customers” to “our customers.”