The Customer Success Café Newsletter

The Customer Success Café Newsletter

Proof, Not Process: Turn CS Plays Into Promotions

The Customer Success Café's avatar
The Customer Success Café
Nov 09, 2025
∙ Paid

Win first, workflow second.

Most CS teams build playbooks like project plans: kickoff, handoffs, tasks. It looks neat. It doesn’t move revenue.

The only question that matters is: what’s the customer’s first meaningful win, and how fast can you get them there? Everything else is scaffolding.

Below is a no-fluff system you can ship this week.

Use it to protect renewals, create expansion proof, and show leadership you can scale outcomes, not paperwork.


Outcome-Led Playbooks (Not Activity-Led)

Define the first win, then reverse-engineer milestones and actions.

Outcome Layer (one line, measurable)

  • “Marketing sends 80% fewer internal emails by Day 30.”

  • “Support resolves Tier-1 tickets in <2 minutes by Week 3.”

  • “Finance closes books 2 days faster this month.”

Rules: outcome = the customer’s result (%, time saved, errors reduced, revenue protected).

Milestone Layer (3–5 steps that pull the metric)

  1. Access + core setup complete

  2. First workflow live for one team

  3. DAU/WAU crosses X%

  4. “Aha” moment with before/after proof

  5. Outcome met, owner signs off

Action Layer (lean tasks serving milestones)

  • “Install SSO; owner: IT; trigger: countersign”

  • “20-min manager rundown; owner: CSM; trigger: first login”

  • “Import last 30 days; owner: Admin; trigger: API key created”

If an action doesn’t serve a milestone, cut it.


First-Value Sprint In 30 Days

Stop shipping 90-day plans.

Run one sprint to land a win that customers can feel, just like the 30-day anti-churn framework that helps save at-risk accounts.

Cadence

  • Day 0–3: confirm the win, lock access, configure one use case

  • Day 4–10: manager enablement + team activation

  • Day 11–20: usage ramp; remove friction; tighten integrations

  • Day 21–30: measure, document proof, secure written sign-off

Proof Pack

  • 1 baseline vs. current metric

  • 1 annotated screenshot/log

  • 1 stakeholder quote

  • Next 2 expansion plays with value hypothesis


Decision Branches Beat Scripts

Adapt by Size, Maturity, and Risk.

By Size

  • <50 users: CSM-led enablement; async training

  • 50–500: manager-led; cohort training; usage alerts

  • 500: change plan; champions; exec cadence

By Maturity

  • Low: smaller targets; more templates; tighter check-ins

  • High: faster rollout; self-serve; more automation

By Risk

  • No login 7 days → friction sweep + manager call

  • IT block → exec sponsor ping + alt path (CSV)

  • Power user plateau → advanced workflow + value calculator


Automation That Actually Helps

Tie actions to events, not calendars.

This is where customer success lifecycle automation becomes your force multiplier.

  • No login 5 days → task “Friction sweep” + 2-min rescue guide

  • Usage >X% for 7 days → open expansion opp with hypothesis

  • Key feature unused Day 10 → auto-invite to micro-training

  • Stakeholder change → “re-anchor value” sequence


Metrics That Predict Renewal

Track outcomes, not activity completion.

  • Time to First Value (TTFV)

  • Milestone conversion (M1→M2→M3)

  • Breadth of adoption (active/licensed by role)

  • Depth of adoption (critical features/week)

  • Early renewal signals (exec activity, value sign-off, multi-threading)

  • Expansion readiness (# of quantified hypotheses with owners)

Weekly Review:

  • Red = missed milestone + no owner

  • Yellow = friction

  • Green = outcome + next value scoped.


Operating Rhythm That Scales

Fridays (20 min): outcome proofs landed, stalls + one fix, unused step to remove, surprise wins to standardize.

Monthly (45 min): update templates, refresh proof examples, promote 1–2 plays to “standard.”

Your Career Leverage With Executives

Show drops in TTFV, higher Day-30 health, rising expansion from outcome proofs, and capacity wins from automation.

Package it as a quarterly CS Value Report. That’s how you move into staff+ and leadership roles that command $120k-$200k+ compensation.


Pitfalls To Eliminate

  • Activity worship: “100% tasks done” with zero outcome proof

  • 20-page playbooks nobody opens

  • One playbook for SMB and Enterprise

  • Timeline-only automations

  • “We’ll review next quarter”


Ship This Next Week

  • Day 1: pick one segment + one outcome. Write the one-line win.

  • Day 2: map 3–5 milestones. Remove stray actions.

  • Day 3: set 4 event-based automations.

  • Day 4: run a First-Value Sprint with two pilots.

  • Day 5: publish your first Proof Pack; book stakeholder readout.


”Hakan’s newsletter provides tactical examples and resources that can be adopted, rather than just listing buzzwords.” — Carissa Jaji, Senior Director, Client Success @ Ontheside

”The CS Café is incredibly valuable! It gives a view on how and what to do next.” —Lara Barnes, SVP Customer Success


Below are the full templates, scripts, and automation recipes I use with teams to cut TTFV in half. Grab them and ship your first outcome-backed playbook by Friday.


Your Complete Implementation Kit Below (Copy-Ready | Fill-In Template)

Want the executive reporting template that turns your playbook metrics into promotion evidence?

Reply with your current role and I’ll send you the customized version that fits your career stage.

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