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The Customer Success Café Newsletter

Why You’re Not Landing Director/VP CS Roles (And How To Fix It)

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The Customer Success Café
Nov 02, 2025
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Stop Speaking Ops. Start Speaking P&L.

Executives already assume you can run 1:1s, fix escalations, and ship playbooks.

They’re testing one thing:

Do you think in revenue terms, and can you recommend what to do next?

The Manager-To-Executive Language Gap

  • Managers describe activities.

  • Directors/VPs price outcomes, forecast impact, and recommend allocation.

If your best stories sound like “we improved onboarding by 30%”, you’re still speaking ops.

Executives hire P&L translators, people who turn customer work into retention, expansion, and margin.


What Executives Actually Listen For

  1. Economic framing

    “Delays in onboarding were deferring ~$400k in expansion per quarter. We re-sequenced the journey and pulled that revenue forward by one quarter.”

  2. Segmented insight

    “41% of enterprise logos breached time-to-first-value >21 days due to SSO and data mapping.”

  3. Clear recommendation

    “Shift two CSM FTE to enterprise activation; add weekly cohort sessions; expected recovery $350k in two quarters.”

Activities are assumed. Pricing, segmentation, and recommendations are what get you hired.


Executive Answer Framework (PAER): Overview

The PAER framework structures executive-level answers around four business-driven components:

  • (P) roblem (business-level): NRR, churn, payback, LTV/CAC.

  • (A) nalysis (segmented + causal): Where it concentrates and why.

  • (E) conomic impact ($ / ARR / NRR): Size it, even directionally.

  • (R) ecommendation (allocation + ROI): What you’ll do, trade-offs, by when.

Example (old → PAER):

“Reduced TTV by 30%.” →

P: Expansion lagged as activation slipped

A: 41% of enterprise logos >21-day TTFV due to SSO + data mapping

E: ~$400k quarterly expansion deferred

R: Re-sequence onboarding, move 2 FTE to enterprise activation, add weekly cohorts

→ recover ~$350k within two quarters.


Manager-Speak → Exec-Speak (Quick Swaps)

  • “We ran QBRs”

    → “Standardized QBRs for top 20% logos; expansion win rate +11 pts.”

  • “Built health score”

    → “Surfaced $2.3M at risk; save plays protected $1.4M ARR.”

  • “Improved onboarding”

    → “Re-sequencing pulled ~$400k expansion forward by a quarter.”

  • “Hired 3 CSMs”

    → “Reallocated headcount to enterprise where LTV/CAC is 3.1x vs SMB.”

  • Launched playbooks

    → “Churn 3.2% → 2.1%/qtr, $960k retained.”

  • “Customers said feature X is confusing”

    → “62% enterprise admin drop-off; fix restored +15% MAU.”


A Credibility Booster In 4 Lines

  1. Context: $32M ARR; mid-market churn 18%.

  2. Action: Segmented risk by product fit + value depth; consolidated save plays to 3 moves.

  3. Result: $1.8M ARR recovered in two quarters; NRR improved from 102% → 109%.

  4. Next: Double down on enterprise value depth; expect +3–5 pts NRR.


The Language Upgrade You’ll Use Everywhere

  • “I recommend shifting 40% of CS time to enterprise activation; expansion is 3x vs SMB.”

  • “This saves $900k ARR on current run-rate and pulls $300k expansion forward.”

  • “Trade-off: we will accept a slower SMB response time for two quarters.”

That’s executive posture: priced, prioritized, and honest about trade-offs.

Because when you talk in economics and trade-offs, you sound like someone ready to make $120K–$200K+ decisions.


Common Mistakes That Keep You Stuck

  • Tactical monologues: tools, cadences, templates. No price tag.

  • Anecdotes with no numerator/denominator: “customers felt…”

  • No trade-offs: everything can’t be priority #1.

  • Vague impact: “better,” “improved,” “more”, without $ or %.


🔐Below is the complete playbook: scripts, templates, metrics, and a 7-day plan.

Inside you’ll get:

  • Director/VP interview answer bank (copy/paste scripts)

  • PAER implementation playbook (4 ready-to-use stories)

  • 90-day plan template with explicit trade-offs

  • Quant pack slides (NRR ladder, save plays, expansion map)

  • 7-day sprint to executive-ready

  • Final checklist before final rounds

Plus: Download the NRR Ladder Builder (Interactive Excel Sheets), the artifact that signals you think like a VP. Bring it to every final round.

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© 2025 Hakan Ozturk
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