Customer Success Plan Skill

Customer Success Plan Skill

This skill produces a joint customer success plan — a living document shared between the CSM and the customer that aligns on outcomes, milestones, and mutual commitments. Output is ready to co-author with the customer in a kickoff call or QBR.

Required Inputs

Ask the user for these if not provided:

• Account name and industry
• Product / plan purchased
• Key stakeholders — customer champion and economic buyer
• Customer's stated business goals — why did they buy? What problem are they solving?
• Contract term and renewal date
• Current onboarding stage (new customer / expanding / post-QBR / pre-renewal)
• Seats / licenses / usage purchased
• Any known risks — adoption gaps, champion uncertainty, competing priorities

Output Structure

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Customer Success Plan: [Account Name]

Product: [Product name / plan tier] Contract term: [Start date → Renewal date] CSM: [Name] Customer champion: [Name, Title] Customer executive sponsor: [Name, Title — if known] Last updated: [Date] Status: [Active / Under review / Completed]

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1. Partnership Objectives

What does success look like for [Account Name] at contract end?

[Write 2–3 sentences describing the customer's core objective in plain English — what they are trying to achieve in their business, not what features they are using.]

Primary business goal: [e.g. Reduce time-to-hire by 30% across engineering teams] Secondary goal: [e.g. Consolidate three legacy tools into one platform, saving £X/year] Success statement (customer's words): "[Direct quote from champion about what success looks like — ask for this in kickoff]"

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2. Success Metrics

Define how both parties will measure success. Agreed in the kickoff call and tracked in QBRs.

Metric	Baseline (today)	Target	By when	Data source
[e.g. Seat utilisation]	[X%]	[≥ 80%]	[Month 3]	[Product analytics]
[e.g. Time to hire]	[X days]	[< Y days]	[Month 6]	[Customer's ATS]
[e.g. Reports produced/month]	[X]	[≥ Y]	[Month 3]	[Product analytics]
[e.g. NPS]	[X]	[≥ 8]	[Month 6]	[Quarterly survey]

Leading indicators (early signs the plan is on track):

• [e.g. 5+ users log in within the first 2 weeks]
• [e.g. First workflow automated within 30 days]
• [e.g. Champion presents the tool to their team by end of Month 1]

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3. Milestone Roadmap

Break the success journey into phases with clear milestones and owners:

Phase 1: Onboard (Month 1)

Milestone	Owner	Due date	Status
Admin setup complete (SSO, permissions, data integration)	[IT contact]	[Date]	[ ]
All purchased seats activated and users invited	[Champion]	[Date]	[ ]
Core workflow [X] configured and tested	[CSM + Champion]	[Date]	[ ]
First training session delivered (all teams)	[CSM]	[Date]	[ ]
Kickoff call completed and success plan co-signed	[CSM + Champion]	[Date]	[ ]

Phase 2: Adopt (Months 2–3)

Milestone	Owner	Due date	Status
[Core feature] in active daily use by ≥ X users	[Champion]	[Date]	[ ]
First business outcome achieved and documented	[Champion + CSM]	[Date]	[ ]
30-day check-in completed	[CSM]	[Date]	[ ]
[Power user workflow] enabled for advanced users	[CSM]	[Date]	[ ]

Phase 3: Value (Months 4–6)

Milestone	Owner	Due date	Status
QBR 1 delivered — ROI evidence presented	[CSM + AE]	[Date]	[ ]
Success metric [X] hit target	[Champion]	[Date]	[ ]
Expansion use case identified and introduced	[AE]	[Date]	[ ]
Reference call or case study agreed	[Champion]	[Date]	[ ]

Phase 4: Renew & Expand (Months 7–12)

Milestone	Owner	Due date	Status
QBR 2 delivered — renewal conversation started	[CSM + AE]	[Date]	[ ]
Renewal proposal sent	[AE]	[Date]	[ ]
Expansion or flat renewal signed	[AE]	[Date]	[ ]

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4. Mutual Commitments

Success plans work when both parties commit. Document what each side will do:

[Vendor] commits to:

• Dedicated CSM available [X days/week / by email within 24 hours]
• Monthly [call / check-in / async update] with champion
• QBR every [90 days] with executive summary and ROI report
• Priority support for [Account] — response SLA of [X hours] for P1 issues
• Roadmap preview for relevant upcoming features
• [Any other specific commitment made in sales cycle]

[Account Name] commits to:

• Champion available for [30-min monthly] check-in
• Users complete onboarding training by [date]
• Feedback on product experience shared monthly (async or sync)
• Executive sponsor participates in QBR 1 and renewal discussion
• Provide outcome data to CSM quarterly for ROI tracking

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5. Stakeholder Engagement Plan

Stakeholder	Role	Engagement frequency	Format	Owner
[Champion]	Day-to-day owner	Weekly (async) + Monthly (call)	Slack / Email + Zoom	CSM
[Economic buyer]	Budget holder	Quarterly	QBR (in-person or video)	CSM + AE
[IT contact]	Integration owner	As needed	Email	CSM
[End users]	Active users	Training only	Group session	CSM

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6. Risk & Mitigation

Risk	Likelihood	Impact	Mitigation plan
Low adoption in first 30 days	[M]	[H]	CSM hosts live onboarding; champion sends internal comms day 1
Champion changes role	[L]	[H]	Multi-thread: introduce CSM to 2 additional stakeholders by Month 2
Budget pressure at renewal	[M]	[H]	Build ROI case monthly; document value continuously
Competing priorities delay rollout	[H]	[M]	Agree minimum viable adoption path with champion; don't require perfection to declare value

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7. Communication Plan

Communication	Audience	Frequency	Format	Owner
Health update	Champion	Monthly	Email summary (3 bullets: what's good, what needs attention, one ask)	CSM
QBR	Champion + Exec	Quarterly	45-min video call with slide deck	CSM + AE
Product updates	Champion	As released	Release notes email	CSM
Support status	Champion	When open tickets exist	Email / Slack	Support + CSM

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8. Escalation Path

If the success plan falls off track:

Trigger	Action	Owner	Timeline
Health drops to Amber	Internal review + champion call within 5 days	CSM	Immediate
Health drops to Red	CS leadership + AE looped in; escalation brief drafted	CS Manager	Within 24 hours
Champion is unresponsive for >10 days	AE attempts exec sponsor contact	AE	After CSM attempt fails
Adoption <40% at Month 3	Emergency enablement session + revised milestone plan	CSM	Within 1 week of flag

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Deeper Materials

This skill ships with support files — use them when they are available:

• references/outcome-contracting.md — Outcome Contracting: Success Plans That Bind Both Sides. Apply it while producing the output; it carries the calibration and judgment calls the method summary above compresses.
• templates/success-plan.md — a fill-in version of the deliverable with the quality gates inline. Offer it when the user wants to work the document themselves rather than have it generated.

Scoring Rubric (0–40)

Score any output of this skill before handing it over; 32+ is ship-quality.

Dimension	0	5	10
Outcome orientation	All metrics are vendor-controlled product-usage numbers	Customer business metrics present but missing baselines, targets, or data sources	Customer business outcomes with baseline, target, date, and data source — plus leading indicators
Ownership & dates	Owners blank, "CS team", or dates left TBD	Owners named on the vendor side only; customer-side milestones unowned	Every milestone has a named owner on the correct side of the table and a confirmed date
Mutuality	Reads as the vendor's internal to-do list	Customer commitments listed but vague or clearly not agreed	Both sides carry concrete commitments; executive sponsor has a named engagement role; shareable as written
Risk realism	No risk register	Generic risks; champion departure and low adoption missing	Includes champion departure and low adoption with mitigations, owners, and escalation triggers

Quality Checks

• Success metrics are the customer's metrics — not just product usage metrics
• Milestones have specific owners and due dates — not "TBD"
• Mutual commitments section is genuinely mutual — not just what the vendor will do
• Risk register includes champion departure and low adoption
• Plan is written to be shared with the customer — no internal-only commentary in this document
• Executive sponsor is identified and has an engagement role

Anti-Patterns

• Do not define success metrics that the vendor controls — metrics must reflect the customer's business outcomes
• Do not set milestone dates without customer confirmation — unilateral timelines undermine joint ownership
• Do not create a plan the customer hasn't agreed to — it must be mutual, not a CSM's internal plan
• Do not leave ownership fields blank or assigned to "CS team" — every action needs a named owner
• Do not confuse product adoption milestones with customer business outcomes — both are needed but are not the same

Example Trigger Phrases

• "Build a success plan for [Account Name] who just signed"
• "Create a joint success plan for our new enterprise customer"
• "Write a 6-month customer success roadmap for [Company]"
• "I need a mutual action plan for our QBR with [Account]"
• "Generate a customer success plan for an at-risk account"