Why I'm starting a newsletter for Client Success Managers

Hey, it's Diego.

This is the very first CSM Council Newsletter, so before we get into playbooks and scripts, I want to tell you why I'm writing it.

Short version: coaches keep asking me the same question, and I'm tired of not having a better answer.

Here's the longer version. 👇

I used to be a chef

Before any of this, I worked in kitchens. Ten to twelve hour days, on my feet, in the heat, every weekend gone.

I hated it. Not the cooking, the life around it.

So I changed careers and moved into remote work. It was one of the best decisions I've made. I work with smart people, I solve real problems, and I don't smell like a fryer when I get home.

I'm telling you this because a lot of you are where I was. Maybe you're in a job you don't love and client success looks like a way out. Maybe you already made the jump and now you want to get really good at it. Either way, I've been on both sides of that switch.

What I do now

Today I run an agency called Scale With Fulfillment. I work as a fractional COO inside coaching offers, some of them doing million-dollar months, and I run their fulfillment.

That means I hire Client Success Managers constantly. I've done more CSM interviews over the past five years than I can count.

And here's what I learned: good CSMs are really hard to find.

Not because people aren't smart or hardworking. Most of the candidates I meet are both. They're stuck for other reasons:

• They do support, not results. Their day is inbox and check-ins. They never get to the part of the job where you actually change someone's outcome.
• Nobody trained them on renewals and upsells. That's where a CSM creates the most value, and where commission often lives, if the company offers it. Most avoid it because it feels like sales.
• They can't prove what they can do. Smaller offers rarely give you a chance to show your skills. So you end up competing on price.

Meanwhile, coaches keep messaging me: "Diego, do you know a good CSM?" Friends, clients, people I met once at an event.

For a while I just passed along whoever I'd worked with. But there were never enough names, and the coaches who ask usually don't have time to train someone from scratch.

So I started thinking: what if there was one place where CSMs could actually learn the job properly, practice the hard conversations, and connect with people further along?

That's CSM Council. And this newsletter is the part anyone can read.

What you'll get from me

Two emails a week. Short, practical, built to use the same day.

Every Tuesday: a playbook. One skill, broken down step by step. Onboarding calls, check-ins, renewal conversations, spotting upgrade moments, reporting to a founder. With scripts and message templates you can copy.

Every Friday: a scenario. A situation every CSM hits sooner or later. A client asks for a refund on day 9. Someone goes silent for two weeks. A high-ego client pushes back on everything. I'll walk you through how I'd handle it, what to say, and what to avoid.

No fluff, no motivational quotes. Just the stuff I wish someone had handed me, and the stuff I look for when I hire.

Who this is for

Two kinds of people.

Working CSMs who want to become S-Tier. You already have clients. You're good at the day-to-day. Now you want to handle refund calls without sweating, lead renewals with confidence, and be the CSM a coach would never want to lose.

People new to client success. Maybe you're coming from hospitality, teaching, fitness or sales, like I came from a kitchen. You already have more of the skills than you think. You just need to learn how coaching offers work and how to talk to clients inside them.

If you're one of those two, you're in the right place.

Try this this week: Write down the one client conversation you dread most. The refund request, the "I'm not seeing results" message, the upgrade talk you keep putting off. Hit reply and tell me what it is. I read every answer, and the most common ones become Friday scenarios.

One more thing. I'm not going to promise you a job or a number on your paycheck. What I can promise is that every newsletter will make you a little better at the work. Do that for a few months and people start to notice.

Talk soon, Diego

P.S. If you want to go deeper than email, with the full playbooks, frameworks and a community of CSMs to learn from, here's what the CSM Council community looks like.