Feature Story
Every time I started a new CS leadership role, I ran the same play.
Within the first week, I mapped my customer base into tiers. Not fancy tiers. Just: who is at risk, who is high revenue, who is renewing soon, and who do we actually have a real relationship with at the executive level?
Then I started reaching out. Personally. I didn’t have the CSM do it, I didn’t have them join me. Just me and our customers.
The email I sent was simple. I'm new, you're important, I want to hear directly from you. I didn’t have a crazy agenda, no slides to walk through, just a 30-minute conversation.
And people said yes. In fact, most of them did and they were excited to hear from me.
Here's what I learned in those meetings that no dashboard ever told me: our product wasn't meeting a key need for a segment of our book. Our CS team had great relationships with the wrong people at half our accounts. And several customers were quietly shopping alternatives because we'd never thought to ask if they'd renew.
I ran this same playbook at three different companies and every time I did it changed my strategy within the first 90 days.
Executing this program allowed me to uncover risk, opportunity and gained me and the company brownie point with a lot of our companies.
Running this program I made sure I was asking consistent questions, documenting the answers, recording the calls, and manually analyzing what I heard. Back then I had no AI so it was just me a spreadsheet and a lot of coffee (and some tea).
See you all have tools I didn't have. You can synthesize 30 customer conversations in minutes. You can spot themes across a book of business before you've finished your second month. You can walk into an executive meeting with a customer narrative that would have taken me an entire quarter to build. So there is no excuse not to do this.
And yet, most new CS leaders still aren't doing this.
The Takeaway: The first 90 days of a new CS leadership role are the most valuable market research opportunity you will ever have. Customers will tell you things they won't tell your team. Use your newness intentionally, because you only get it once.
AI IN CS
This is exactly where AI should be doing the heavy lifting.
The program I ran manually took real time. Prepping for each meeting meant digging through CRM notes, ticket history, and NPS scores one account at a time. Synthesizing themes across 30+ conversations meant building my own coding system in a spreadsheet. It worked, but it was slow.
Today, you can prompt your AI tool to pull a pre-meeting brief on any account in under two minutes. You can drop your call transcripts into a doc and ask Claude or ChatGPT to surface the top five recurring themes across your entire first wave of meetings. You can use AI to draft your follow-up emails, flag sentiment shifts, and build the synthesis deck you'll present to your exec team at day 90.
The strategic play is the same as it always was. The manual work is gone. And YES, I am jealous.
If you're running this program right now and you're still doing the synthesis by hand, you're leaving hours on the table. Build a simple prompt library for your meeting prep, transcript analysis, and post-program summary. The insight is yours, but let the AI do the extraction.
THE RESOURCE
This week's resource is the full playbook behind what I described above.
It includes:
A quick-start week-by-week timeline for days 1 through 120
Tone calibration guidance by account health (you should open a red account conversation very differently than a green one)
The exact follow-up sequence for non-responders
A meeting agenda with specific questions including the renewal question I ask every single time
An account tracker template you can use in a spreadsheet or your CSP
This is the full playbook. Use it in your first 90 days or send it to a new leader who needs it.
FROM MY WORLD
Quick updates … Events, podcasts, awards, news, etc.
EPS #7: It’s not them. It’s You. Why Execs Aren’t Showing Up and What to Do.
How to rearchitect your business review process to host conversations your customers find valuable.
The Spy Turned CCO at People.ai featuring Natalie Wolf
Listen to Natalie’s path to the C-suite and her advice on ownership, courage, and owning your own playbook.
CCO SUMMIT SILICON VALLEY
Chief Customer Officer Summit Silicon Valley: April 15th
Join me and tons of leading CCOs and those shaping the future of customer-centric strategy for a day of unrivaled networking, learning, and discussion.
ATLCS SUMMIT
I’m the Keynote Speaker at the ATLCS Summit: April 23rd
Summit is the premier gathering for CS thought-leadership in the Southeast. An interactive, one-day event built for customer practitioners and leaders.
POLL
When you started your last CS leadership role, how did you approach your first 90 days with customers?
A FINAL NOTE
CLOSING WITH KRISTI
Newness is not a weakness. It's a permission slip.
Use it to get access to the rooms your team hasn't been in. Use it to ask the questions that feel too direct once you've been around long enough to know better. Use it to build a customer narrative that actually reflects reality, not what your CRM says.
And when that window closes, and it will close, you'll have a foundation that the rest of your first year gets built on.
You only get to be new once. Make it count.
See you next week,
Customer Success. Revenue Follows.