Shadow Your Top CSM—Save Month Two
The Trap That Tanks Month Two
You just got promoted to Head of CS at a mid-stage startup.
Leadership is excited. Your team is watching.
You’ve got 200+ customers, zero formal structure, and you’re thinking: “I need to overhaul everything. Fast.”
So you start building on Day 1: new health scores, playbooks, dashboards. It feels like progress.
Then month two hits. Renewal rate dips. Your CEO notices. Your best CSM says, “This process doesn’t match how I actually work.” The team resists. Retention slips.
You replaced what was working with theory.
The reality is that if 200+ customers stuck around without formal CS, something is already working. It’s just invisible. It lives in people, not systems.
When you ship process before you understand that invisible system, you slow down, lose credibility, and miss your window to earn trust and budget.
There’s a better sequence.
Week 1 Move in 3 Steps: Shadow, Extract, Encode
Shadow your top CSM for a full week.
Extract the exact moves that keep accounts, surface risk, and create expansion.
Encode those moves into the lightest possible structure.
What to capture
Conversations that actually shift renewal odds.
Leading signals that trigger action (usage cliffs, sponsor change, “silent success,” onboarding stalls, billing issues).
How quiet-but-healthy accounts stay engaged.
Where work gets blocked (authority gaps, unclear success criteria, internal SLAs).
Patterns You’ll Uncover
Results hinge on a few repeatable moves, not 40-page playbooks.
Knowledge sits in people, not systems. Great for now, risky for scale.
“Gut feel” is just unnamed signals. Name them. Share them.
90-Day Sequence That Preserves Momentum
Days 1–7: Observe and write the Signals > Score list (3–5 leading indicators), a Renewal Path outline (T-90/T-60/T-30), and a Weekly Rhythm draft.
Days 8–30: Define 3–4 segments you actually serve.
Write segment health. Ship 3 micro-processes:
Signals checklist,
Renewal Path,
Weekly Rhythm.
Days 31–60: Turn notes into two-page guides, pilot with 2–3 CSMs, coach with call scorecards tied to signals.
Days 61–90: Standardize, record examples, train new hires, and publish a win ledger (signals caught → actions → dollars saved/expanded).
Exec Credibility Without The Theater
You’re not “installing” CS. You’re scaling what already wins, adding only what’s missing.
That’s how you earn budget and trust.
Common Mistakes New CS Leaders Make
Shipping complex health scores before naming real signals
Start with 3–5 leading signals; layer scoring later.Building playbooks nobody follows
Write 2-page guides from your top CSM’s language; pilot with two reps first.Reorganizing before you’ve watched the work
Shadow first; change roles only after you see patterns.Hiring CSMs who optimize for activity, not outcomes
Interview for renewal saves and expansion proof; score outcomes, not tasks.
These mistakes are why the toolkit below matters → it prevents all four with templates, scripts, agendas, and scorecards you can ship this week.
Join The CS Cafe Premium. Get two pages per asset. Copy, paste, run.
30/60/90 Delivery Checklist (Print This)
By Day 7: