Robert Statsky

Turn an Org Around in 60 Days: B2B SaaS Customer Success

What to do when you’re a new leader on a deadline? Well, let’s consult our business analyst first…

PROMPT:

You have recently joined a B2B SaaS organization as the head of customer success. You need to develop talent, update systems, develop process, and institute change that is going to have positive customer outcomes. As part of this you are responsible for revenue growth, retention, expansion, onboarding, support, and employee development. You will have to save customers. The company is currently working off a spreadsheet and being very reactive instead of thinking ahead proactively on how to develop better clients and advocates. You are not going form 0 to 1, you are going from -10 to 0. How do you get there, where do you start, what does the first 30 days look like? The first 60?

Context: Starting from –10 → 0. You own retention, expansion, onboarding, support, and talent. Goal: stabilize, install operating system, and prove outcomes inside 60 days.

North Star (what “0” looks like)

  • Forecast: 90‑day renewal forecast within ±10%, owner per account.
  • Customers: Every $ account has an active Success Plan + exec sponsor.
  • Ops: Single source of truth, Health Score v1, lifecycle playbooks live.
  • Team: Clear coverage model, weekly rituals, coaching cadence.

Days 0–30: Stabilize & Lay Foundations

Week 1 — Triage & Truth

  1. Account Heatmap (today): ARR | Renewal Date | Stage | Risk (R/Y/G) | Top 3 Risks | Exec Sponsor | CSM | Next Action | Date.
  2. Save Desk (48h): daily 30‑min war‑room on top renewals (<120 days) + reds. One owner, one next step, one date.
  3. Customer Reset: message to all; 1:1 calls with top 20 ARR. Ask: What works? What’s not? What must be true by renewal?
  4. Support Relief Valve: Sev1/2 board w/ ETAs; 24h first‑response SLA; hot lane for renewals <120 days.
  5. Team Scan: 1:1s; book, strengths, risks; pair senior support on top saves.

Outputs by Day 7: Heatmap v1, Save Desk running, critical ticket board, coverage snapshot.

Weeks 2–4 — Foundations You’ll Keep

  1. Segmentation & Coverage: Enterprise / MM / SMB; target ratios (e.g., Ent 1:15–25, MM 1:35–50, SMB pooled).
  2. Lifecycle Playbooks: Onboarding (TTFV goals, milestones, risk gates) → Adoption/Value (monthly checkpoints) → Renewal 120/90/60/30.
  3. Success Plans: 1‑page: Objective → KPI → Use Cases → Owners → Risks → 30/60/90 steps. 100% Ent / 80% MM by Day 30.
  4. Source of Truth: Move off sheets into Airtable/Notion/CRM object; weekly import of usage + support tags.
  5. Health Score v1 (simple): Use (40) • Exec Sponsor (20) • Support friction (15) • Onboarding/Value (15) • Engagement (10). Red <50.
  6. Operating Rhythm: Daily Save Desk; Weekly Renewals forecast + Product sync; Monthly CS Ops read‑out.
  7. Change Comms: Publish CS Turnaround Charter; celebrate 2 quick wins.

30‑Day Targets:

  • Renewal forecast in place; owner + probability per deal.
  • Top 20 at‑risk have save plans; 70%+ ARR with active Success Plans.
  • Health v1 live; first Red→Yellow conversions.
  • Critical ticket backlog ↓30%; 24h first‑response ≥95%.

Days 31–60: Instrument, Scale, Prove

  1. Tooling & Data: Pick CS platform (Gainsight/Totango/Planhat/Catalyst). Phase‑1: Account 360, health, CTAs, playbooks, EBRs. Pipe product telemetry + CRM + support.
  2. Onboarding 2.0: Segment TTFV targets (Ent ≤30d, MM ≤14d, SMB ≤7d). Add risk gates → auto‑CTAs. Ship a Customer Launch Kit.
  3. Value Story / EBR Upgrade: Outcome slide: baseline → current → ROI; exec‑to‑exec EBR for top 25 quarterly.
  4. Expansion Engine: Signals → CTAs (usage, breadth, feature interest, anniversary). Create CS‑Qualified Expansion (CSQE) → Sales. Track $ pipeline from CS.
  5. Churn Reasons & Close‑Loop: Fit / Value / Product / Service / Budget. Assign corrective owner; review bi‑weekly.
  6. Talent & Coaching: Scorecard (coverage, saves, forecast accuracy, EBR quality, NPS/CSAT, expansions). Weekly call reviews; visible ladder.
  7. Voice of Customer: NPS (2‑Q), CSAT/CES at key touchpoints, renewal win/loss; publish Monthly VOC Brief (themes + actions).

60‑Day Targets:

  • Forecast variance ±10–15%; renewals staged 120/90/60/30 with plans.
  • GRR stabilized; early NRR lift from expansion motions.
  • TTFV on target for 70% of new logos.
  • ≥90% accounts scored; Red ARR <15% (all with save plans).
  • EBR: 80% of top 25 completed/scheduled with outcomes.
  • CS platform Phase‑1 live; dashboards for renewals & expansion.

Core Playbooks (condensed)

Renewal 120/90/60/30

  • 120: Validate success plan, align stakeholders, pre‑close risks.
  • 90: Commercial pre‑wire, exec sponsor sync.
  • 60: Draft order form, legal pre‑check, usage/value recap.
  • 30: Close; schedule post‑renewal EBR + expansion discovery.

Save (any Red)

  1. Diagnose (root cause + proof) → 2) Contain (hotfix; exec call <48h) → 3) Prove progress (time‑boxed milestones) → 4) Recovery offer (if needed) → 5) Post‑mortem + prevention.

Health Score v1 (example)

DimensionWeightSignals
Product Use40DAU/WAU vs licenses, breadth by team
Exec Sponsor20named sponsor, access, cadence
Support Friction15Sev count, aging, CSAT
Onboarding/Value15milestones met, TTFV achieved
Engagement10EBRs, meetings kept, survey response
**Red <50Yellow 50–74Green ≥75**

Operating Rhythm

  • Mon: Save Desk + backlog review
  • Tue: Renewals forecast (CS/Sales/Finance)
  • Wed: Product/VOC sync (top 3 themes → owner & ETA)
  • Thu: Coaching (call reviews + playbook drills)
  • Fri: Metrics read‑out + customer win of the week

KPIs & Dashboards (minimum)

  • GRR, NRR, churn/expansion by segment
  • Forecast variance (90‑day), renewal stage coverage
  • TTFV by segment; onboarding risk gates breached
  • Health distribution (% Red ARR), Red→Yellow conversion rate
  • Support: first‑response SLA, backlog aging, Sev trend
  • EBR coverage and CS‑sourced expansion pipeline

Stop Doing (now)

  • Treating all tickets equally → Prioritize by ARR × Renewal proximity × Severity
  • Feature‑tour QBRs → Outcome‑led EBRs
  • Spreadsheet as system → Structured source of truth (Week 3)
  • Random heroics → Playbooks + CTAs logged to system

The above strategy was provided by Chat GPT via that exact prompt. I can say with 100% confidence after doing this for nearly 20 years that with that you can use that information as a very solid foundational starting point for getting your CS house in order. While this is certainly a B2B SaaS CS lens, it could be applied to any role, and I’d strongly encourage anyone to do that.

Back to List