4-Week Live Cohort · For Working CSMs

Reclaim 5+ hours a week and run sharper accounts — with AI doing the busywork.

A hands-on, live cohort that teaches working Customer Success Managers to build real AI workflows — account prep, QBR decks, renewal risk, save plays — using Claude and ChatGPT. No theory. You leave every session with an artifact you use at work the next morning.

8 live sessions over 4 weeks
Weekly office hours for your real accounts
Every template included — yours to keep
Capped at 20 seats · first 10 seats get early-bird pricing
The Problem

You already know AI could help. Nobody has shown you how — for your job.

Your week disappears into prep

QBR decks, call prep, meeting notes, follow-up emails, CRM hygiene. The strategic work — the reason you took this job — gets whatever's left over.

Generic AI courses don't transfer

"Prompt engineering 101" doesn't tell you how to prep a renewal conversation, draft an exec-ready QBR narrative, or triage a 40-account portfolio.

The bar is moving

CS teams are being asked to carry more accounts with fewer people. The CSMs who build AI leverage now will set the standard everyone else is measured against.

Fit Check

Who this is for — and who it isn't.

This is a working course for practitioners. Every exercise uses your real book of business (sanitized). If you can't bring real work to class, you won't get the value.

Built for you if you are

  • A working CSM, Senior CSM, or account manager with a live portfolio right now
  • A CS team lead who wants to model AI workflows before rolling them out to the team
  • Comfortable in your CS stack but a beginner-to-intermediate with Claude or ChatGPT
  • Willing to spend 3–4 hours a week for 4 weeks, including live sessions
  • Ready to apply exercises to your actual accounts, not hypotheticals

Not for you if you want

  • Executive "AI strategy" theater — frameworks, vision decks, and no keyboard time
  • A general prompt-engineering course untethered from CS work
  • A tool-buying guide — we use the AI assistant you already have access to
  • Passive video content — this is live, hands-on, and homework is real
  • A magic bullet — AI compresses your busywork; it doesn't do your job
Curriculum

Four weeks. Eight live sessions. A working system by the end.

Each week has two live 60-minute sessions plus office hours. Every session produces a concrete artifact you keep and use immediately.

Week 1

Account Intelligence & Prep Automation

Stop walking into calls cold. Build the machine that briefs you.

Session 1
Your AI Operating Setup + First Account Brief

Set up a safe, repeatable workspace (projects, custom instructions, data-handling rules). Build your first one-page account brief from raw notes, emails, and CRM exports.

Session 2
The 10-Minute Call Prep System

Turn any upcoming meeting into a prep sheet: attendee context, open threads, likely objections, and your three goals — generated in minutes, refined by you.

You leave with:
  • A personal AI workspace configured with your data-safety rules
  • A reusable Account Brief prompt template, tested on 2 of your own accounts
  • A Call Prep One-Pager template that runs in under 10 minutes
Week 2

Customer Communications That Land

QBRs, emails, and follow-ups — drafted in your voice, at exec quality, in a fraction of the time.

Session 3
QBR / EBR Decks From Raw Data

Go from usage exports and meeting notes to a business-review narrative and slide outline: value delivered, gaps, and the ask. Includes the exec-summary pattern that survives a skimming VP.

Session 4
The Email Engine: Voice, Follow-Ups, Hard Messages

Build a style guide the AI writes in — your voice, not robot voice. Then drill the three hardest email types: post-call follow-up, escalation response, and the nudge to a silent stakeholder.

You leave with:
  • A QBR narrative + slide-outline generator fed by your own account data
  • A personal voice/style guide file that makes every AI draft sound like you
  • A tested library of email patterns for follow-ups, escalations, and re-engagement
Week 3

Risk, Renewals & Save Plays

See churn coming earlier, and walk into every renewal with a plan.

Session 5
Health Signals: Reading Risk From What You Already Have

Use AI to mine your notes, tickets, and usage patterns for early risk signals your health score misses — sentiment drift, stakeholder churn, shrinking engagement — and rank your portfolio by real risk.

Session 6
Renewal Prep & the Save-Play Builder

Build a renewal-brief generator: contract context, value story, risk factors, expansion angles. Then construct save plays for your two most at-risk accounts — live, with peer and instructor review.

You leave with:
  • A portfolio risk-review workflow you can run weekly in ~20 minutes
  • A Renewal Brief template covering value story, risks, and expansion angles
  • Two written save plays for your own at-risk accounts, reviewed in session
Week 4

Scale: Your Personal Playbook & Portfolio Operations

Turn four weeks of workflows into a durable system that runs your whole book.

Session 7
Portfolio Operations: The Weekly AI Cadence

Assemble the pieces into a weekly operating rhythm: Monday portfolio triage, daily call prep, Friday pipeline-and-risk review. Design your personal cadence around your real calendar and account load.

Session 8
Your Playbook, Your Prompt Library, Your Next 90 Days

Finalize your personal playbook and prompt library. Present one workflow to the cohort. Leave with a 90-day plan for deepening the system — and the peer group to hold you to it.

You leave with:
  • A complete personal playbook: every workflow from the course, tuned to your accounts
  • An organized prompt library (15+ tested prompts) in a format you can maintain
  • A weekly portfolio-ops cadence and a written 90-day improvement plan
Format

Built around a full-time job.

8Live 60-min sessions, recorded if you miss one
4Weekly office hours — bring your real accounts
15+Templates & prompts, yours to keep forever
20Seat cap, so every student gets direct feedback
Instructor

Taught by a practitioner, not a content creator.

GH

Your instructor

13+ years in healthcare SaaS customer success — carrying enterprise accounts, leading business reviews with health-system executives, and managing CS teams through renewals, escalations, and expansions.

For the past two years, he has rebuilt his own CS practice around AI workflows: account intelligence, meeting prep, executive communications, and portfolio risk reviews — the exact system this cohort teaches. Everything in the curriculum is in daily use on real enterprise accounts.

He teaches the way CSMs actually learn: live reps on real work, direct feedback, and templates you can run the next morning.

Pricing

One price. Everything included.

If the course saves you two hours a week, it pays for itself inside the first month at almost any CSM salary. Most students recover far more.

List Price
$500 / seat
Seats 11–20
  • All 8 live sessions + recordings
  • All 4 office-hours blocks
  • Full template & prompt library
  • Cohort peer community
  • Satisfaction guarantee (below)
Join the waitlist
Satisfaction guarantee: attend the first two live sessions and do the Week 1 exercises. If you don't believe the course will earn back your time and money, email me before Session 3 and I'll refund 100% of your seat — no forms, no hassle. After Session 3, seats are non-refundable so the cohort stays committed.

The cohort is capped at 20 students total so everyone gets direct feedback on their real work. When it's full, it's full — the waitlist is first-come, first-served.

FAQ

Questions CSMs actually ask.

How much time does this take per week?

Plan for 3–4 hours: two 60-minute live sessions, roughly 60–90 minutes of homework (applied to your real accounts, so much of it replaces work you'd do anyway), and optional office hours. Sessions are scheduled for working hours in US time zones and recorded if you have a conflict.

What tools do I need? Does my company have to buy anything?

You need a paid plan of either Claude or ChatGPT (roughly $20/month) — whichever your company allows or you already use. Everything in the course works with both; templates are provided for each. No plugins, no API keys, no engineering support required.

We'll also cover how to work safely with customer data: what to sanitize, what never to paste, and how to align with your company's AI policy.

Are sessions recorded?

Yes. Every live session is recorded and available to the cohort within 24 hours. That said, the live exercises and feedback are where most of the value is — aim to attend live and use recordings as backup.

I'm an experienced CSM but new to AI. Is this too advanced?

No — this is the target student. Session 1 starts from a clean setup. What we don't do is spend four weeks on "what is a prompt": by the end of Week 1 you're producing account briefs from your own data. If you already have advanced AI workflows running across your whole portfolio, you may only need the later weeks — email and ask before buying.

Will this work with my company's customer data policies?

The course is built around a sanitize-first workflow: you work with de-identified or dummy-substituted account data by default, and we cover how to check and follow your employer's AI-use policy in Session 1. You never need to share customer data with the instructor or cohort.

Can I expense this to my employer?

Many students do — most companies have a professional-development or L&D budget that covers exactly this. A receipt suitable for expense reports is provided on purchase. Here's a copy-paste request you can send your manager:

Subject: Professional development request — AI for Customer Success Managers ($400–500) Hi [Manager], I'd like to enroll in "AI for Customer Success Managers," a 4-week live cohort (8 sessions + office hours) that teaches CSMs to use AI for account prep, QBR/EBR creation, renewal risk reviews, and customer communications. Why it's worth it for us: - Practical, not theoretical: every session produces a template I'll use directly on my accounts (call prep briefs, QBR narratives, renewal risk reviews). - Time savings: the workflows target the prep and admin work that currently crowds out strategic account time — a realistic estimate is 5+ hours/week recovered. - Transferable: I'll come back with a documented playbook and prompt library the rest of the team can reuse. Cost: $400 (early-bird) or $500 (list), one-time, seat-capped live cohort. Time commitment is ~3–4 hrs/week for 4 weeks, scheduled around normal work hours, with recordings for conflicts. Can I put this on the professional development budget? Thanks, [Your name]
When does the cohort start?

The first cohort's dates are finalized once enrollment opens — waitlist members get first pick of seats and the early-bird price before anyone else. Joining the waitlist is free and doesn't commit you to anything.

What if I join and it's not for me?

The satisfaction guarantee covers you: attend the first two sessions, do the Week 1 work, and if you're not convinced, email before Session 3 for a full refund. No forms, no questions designed to talk you out of it.

Waitlist

Get first pick of the 20 seats.

Waitlist members hear first when enrollment opens and get first access to the 10 early-bird seats at $400. No spam, no commitment — just the launch email.

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