The Journey: #21 The Early Arrival

I’ll never forget one of my earliest wake-up calls in Customer Success.

We were onboarding a string of new customers who were wildly unprepared and it wasn’t their fault, well not really.

They had been promised the moon. Shocker.

Things like:

"Your CSM is basically an extension of your team."

"Don’t worry if you don’t have that, your CSM will build it for you."

And my personal favorite: "No worries, it’s their job."

So there we were, overextended, under-resourced, and starting relationships on a shaky foundation of overpromises and unspoken expectations.

I went to my manager and made what I thought was a logical suggestion, let’s bring Customer Success into the sales process.

Let us meet the prospect.

Let us set realistic expectations.

Let us share how we actually partner with customers.

A few days later, I got the feedback.

“The sales team feels like it’ll slow things down. That CS might overshare and scare prospects. That you're too technical. And… you don’t align with their schedule.”

Ouch. And… also? Not wrong.

I had seen that happen before, even with the best of intentions.

But I didn’t let that shut the door.

Instead, I found a few sales reps I had a great relationship with and said:

Let’s try it, but let’s do it right.

We aligned on three outcomes:

1. Increase deal velocity

2. Set clear expectations

3. Build trust and credibility with the prospect

So we rolled up our sleeves and answered four key questions:

1. Who should be involved from CS?

Not everyone. Just our most experienced, strategic CSMs who were certified in the sales-assist motion. I started as one of them.

2. What role would they play?

Expectation-setter. Product translator. Strategic expert. We let the customer’s needs dictate our role — not our job title.

3. How would we engage?

1:1 virtual meetings after the verbal commit, but before contracts were signed. Occasionally, in person.

4. When should CS show up?

When the deal was verbal but not yet closed.

This helped the AE stay engaged during procurement limbo and added another layer of value.

And it worked. The results spoke for themselves.

• A 7% increase in closed-won deals when CS was attached

• Faster onboarding

• Better-prepared customers

And trust that started before day one

The takeaway?

Bringing CS in early doesn’t create risk, it eliminates it.

But only if you do it with intention, collaboration, and clarity.

You don’t need to crash the deal party.

You just need an invite and a purpose.

What to try this week:

If your CS team isn’t involved pre-sale, start small.

1. Identify a few strategic deals

2. Partner with a few open-minded AEs

3. Outline the goal of your involvement

4. Measure the results

Earn the right to scale. And start talking about the impact Customer Success has on net new revenue and logo acquisition.