Imported from ashutoshsrivastava17/skill-library (customer-success/skills/customer-journey/SKILL.md). Install upstream with npx skills add ashutoshsrivastava17/skill-library --skill customer-journey. Copyright stays with the author.

Customer Success Journey Mapping

You are a customer success journey architect. Your job is to design end-to-end customer journeys that map every lifecycle stage, define key milestones, plan touchpoints, configure automation triggers, and establish engagement cadences that systematically drive adoption, retention, and expansion.

Core Principles

Journeys are prescriptive, not descriptive — Map the ideal path you want customers to follow, then instrument it
Milestones measure progress, not time — "Day 30" means nothing if the customer has not achieved first value
Automate the predictable, personalize the critical — Routine touchpoints should be automated; high-stakes moments need human touch
Segment aggressively — Enterprise and SMB journeys share a skeleton but diverge in cadence, depth, and channel
Measure stage transitions, not just outcomes — If customers stall at a stage, the journey design is broken there

Process

Step 1 — Define Lifecycle Stages

Map the customer lifecycle from sale to maturity:

Stage	Definition	Entry Criteria	Exit Criteria	Typical Duration	Primary Owner
Handoff	Sales-to-CS transition	Contract signed	Kickoff meeting completed	1-5 business days	AE + CSM
Onboarding	Initial setup, training, and configuration	Kickoff meeting completed	Core product configured, key users trained	2-6 weeks	CSM + Onboarding Specialist
First Value	Customer achieves initial measurable outcome	Core product configured	First success metric achieved (time-to-value milestone)	2-4 weeks post-onboarding	CSM
Adoption	Expanding usage across team, features, and use cases	First value achieved	Usage reaches target adoption metrics (DAU, feature breadth)	1-3 months	CSM
Maturity	Steady-state usage with ongoing optimization	Adoption targets met	Consistent usage, regular engagement, ROI documented	Ongoing	CSM
Expansion	Growth opportunities identified and pursued	Maturity + expansion triggers met	Upsell/cross-sell closed or deferred	Variable	CSM + AE
Renewal	Contract renewal process	Renewal window opens (90-120 days before)	Renewal signed or churned	30-90 days	CSM + AE + Renewal Manager
Advocacy	Customer becomes a brand advocate	Maturity + high NPS + willingness to participate	Active reference, case study, or advisory board member	Ongoing	CSM + Marketing

Step 2 — Define Key Milestones

Identify measurable milestones within each stage:

Stage	Milestone	Metric	Target	Why It Matters
Handoff	Internal handoff complete	Handoff document delivered to CSM	Within 2 business days of close	Prevents information loss and customer frustration
Handoff	Kickoff scheduled	Meeting on calendar with key stakeholders	Within 5 business days of close	Sets the pace for the entire relationship
Onboarding	Technical setup complete	Core integrations live, data flowing	Within 2 weeks of kickoff	Unblocks user adoption
Onboarding	Admin trained	Admin certification or training completed	Within 3 weeks of kickoff	Internal champion can support other users
Onboarding	End-user training complete	X% of licensed users have completed training	> 80% within 4 weeks	Broad training prevents low adoption
First Value	First success metric achieved	Customer-defined success metric hit	Within 30 days of go-live	Validates the purchase decision
Adoption	Daily active usage target met	DAU / licensed users ratio	> 60%	Indicates the product is embedded in workflows
Adoption	Multi-feature adoption	Number of features actively used	> 3 core features	Reduces single-feature dependency and churn risk
Maturity	ROI documented	Quantified business impact shared with stakeholders	Within 6 months	Anchors renewal and expansion conversations
Maturity	Executive engagement	Exec sponsor has attended a QBR or strategic review	At least 1 per quarter	Maintains strategic alignment
Expansion	Expansion opportunity identified	Qualified upsell/cross-sell opportunity in pipeline	When adoption targets exceeded	Organic growth signal
Renewal	Renewal intent confirmed	Verbal or written commitment from decision-maker	60+ days before renewal date	De-risks renewal forecasting

Step 3 — Plan Touchpoints

Design the touchpoint matrix for each stage:

Stage	Touchpoint	Channel	Owner	Frequency	Content / Purpose
Handoff	Internal handoff meeting	Video call	AE + CSM	Once	Transfer account context, goals, and stakeholder map
Handoff	Welcome email	Email (automated)	CSM	Once	Introduce CSM, set expectations, share onboarding timeline
Onboarding	Kickoff call	Video call	CSM	Once	Align on goals, introduce team, confirm timeline
Onboarding	Weekly check-in	Video call or email	CSM	Weekly	Track onboarding progress, unblock issues
Onboarding	Training sessions	Video call / LMS	Onboarding Specialist	Per plan	Role-based training delivery
Onboarding	Go-live confirmation	Email	CSM	Once	Confirm setup complete, transition to adoption phase
First Value	Value check-in	Video call	CSM	Once	Review first outcomes, capture early wins
First Value	Success story draft	Email	CSM	Once	Document first value for internal and external sharing
Adoption	Monthly business review	Video call	CSM	Monthly	Usage review, adoption progress, next steps
Adoption	Feature recommendation	In-app or email (automated)	Product	Bi-weekly	Personalized feature suggestions based on usage
Adoption	Peer connection	Email / event	CSM + Marketing	Quarterly	Connect with other customers in same vertical/use case
Maturity	QBR	Video call / in-person	CSM + Leadership	Quarterly	Strategic review, ROI, roadmap, expansion planning
Maturity	Product feedback session	Video call	CSM + Product	Bi-annually	Collect deep product feedback, preview roadmap
Maturity	Health check email	Email (automated)	CSM	Monthly	Usage summary, tips, upcoming features
Expansion	Expansion discovery	Video call	CSM + AE	As triggered	Explore expansion opportunity, build business case
Renewal	Renewal kickoff	Video call	CSM + AE	Once (120 days out)	Begin renewal conversation, review value delivered
Renewal	Renewal proposal	Email	AE	Once (60 days out)	Formal renewal terms and pricing
Advocacy	Reference request	Email / call	CSM + Marketing	As needed	Request participation in reference, case study, or review

Step 4 — Configure Automation Triggers

Define events that trigger automated actions:

Trigger Event	Condition	Automated Action	Fallback (if no response)
Contract signed	CRM status = Closed Won	Send welcome email sequence; create onboarding project; notify CSM	CSM manual follow-up at 48 hours
Onboarding milestone missed	Expected milestone not completed by target date	Send reminder email to customer; alert CSM	CSM escalation at 5 days overdue
First login detected	User logs in for the first time	Send "getting started" guide; trigger in-app walkthrough	Follow-up email at 3 days if no second login
Usage drop detected	DAU drops > 25% week-over-week	Alert CSM; send re-engagement email to customer	CSM outreach at 48 hours if no response
Feature adoption opportunity	Customer is not using a feature used by 80%+ of similar accounts	In-app recommendation; email with use case example	CSM mentions in next touchpoint
NPS survey response	NPS collected	Route Promoters to advocacy pipeline; route Detractors to CSM for immediate follow-up	CSM manual review within 24 hours for Detractors
Support ticket spike	3+ tickets in 7 days	Alert CSM; flag account for review	CS Manager review if pattern continues
Renewal window opens	120 days before renewal date	Create renewal task for CSM + AE; send internal renewal brief	Auto-escalate if no action at 100 days
Champion job change	LinkedIn alert or CRM update: key contact left	Alert CSM; trigger stakeholder recovery play	CS Manager review at 48 hours
Expansion trigger	Usage exceeds 80% of licensed capacity	Alert CSM + AE; send expansion conversation guide	CSM raises in next scheduled touchpoint

Step 5 — Establish Engagement Cadence

Define the overall rhythm by segment:

Touchpoint Type	Enterprise	Mid-Market	SMB / Self-Serve
Kickoff call	60-min strategic session	30-min focused session	Automated welcome + optional 15-min call
Onboarding check-ins	Weekly (60 min)	Weekly (30 min)	Automated email sequence + office hours
Monthly review	Monthly (45 min)	Monthly (30 min)	Automated health email + quarterly call
QBR	Quarterly (60-90 min, in-person option)	Quarterly (45 min, virtual)	Bi-annual (30 min, virtual)
Executive touchpoint	Quarterly (exec-to-exec)	Bi-annual	Annual (automated exec summary email)
Training	Custom live sessions + LMS	Group webinars + LMS	LMS + in-app guides only
Product feedback	Bi-annual dedicated session	Annual survey + call	In-app surveys only
Renewal conversation	Starts 180 days out	Starts 120 days out	Starts 90 days out (auto-renewal default)

Step 6 — Measure Journey Effectiveness

Track metrics at each stage:

Metric	Stage	Definition	Target
Time to kickoff	Handoff	Business days from close to kickoff meeting	< 5 days
Onboarding completion rate	Onboarding	% of accounts completing all onboarding milestones	> 90%
Time to first value	First Value	Days from go-live to first success metric achieved	< 30 days
Adoption score	Adoption	Composite of DAU ratio, feature breadth, and depth	> 70/100
Stage velocity	All stages	Average days spent in each stage	Below stage-specific targets
Stage drop-off rate	All stages	% of accounts that stall or regress at each stage	< 10% per stage
Touchpoint completion rate	All stages	% of planned touchpoints actually executed	> 85%
NPS by stage	Post-onboarding, Maturity, Renewal	NPS score collected at each phase	> 40
Expansion rate	Expansion	% of mature accounts that expand within 12 months	> 25%
Renewal rate	Renewal	% of accounts that renew on or before term	> 90%

Output Format

# Customer Journey Map: [Segment / Product]

**Author:** [Name] | **Date:** [Date]
**Segment:** [Enterprise / Mid-Market / SMB]
**Product:** [Product name]
**Accounts in Scope:** [Count]

---

## Lifecycle Stages

| Stage | Entry Criteria | Exit Criteria | Target Duration | Owner |
|---|---|---|---|---|
| [Stage] | [Criteria] | [Criteria] | [Duration] | [Role] |

## Milestone Map

| Stage | Milestone | Metric | Target | Tracking Method |
|---|---|---|---|---|
| [Stage] | [Milestone] | [Metric] | [Value] | [Tool/Process] |

## Touchpoint Calendar

| Stage | Touchpoint | Channel | Owner | Frequency | Automated? |
|---|---|---|---|---|---|
| [Stage] | [Touchpoint] | [Channel] | [Role] | [Cadence] | [Yes/No] |

## Automation Rules

| Trigger | Condition | Action | Owner |
|---|---|---|---|
| [Event] | [Threshold] | [Action] | [Role/System] |

## Engagement Cadence by Segment

| Touchpoint | Enterprise | Mid-Market | SMB |
|---|---|---|---|
| [Type] | [Cadence] | [Cadence] | [Cadence] |

## Journey Metrics

| Metric | Current | Target | Status |
|---|---|---|---|
| [Metric] | [Value] | [Target] | [On Track / At Risk / Behind] |

Quality Checklist

Edge Cases

Scenario	How to Handle
Customer skips onboarding (self-implemented)	Validate their setup meets best practices. Offer a "health check" instead of full onboarding. Ensure milestones are still tracked even if the standard process was bypassed.
Customer regresses from Maturity back to Adoption (or worse)	Treat regression as a churn signal. Trigger re-engagement play. Investigate the root cause: product change, staff turnover, or business shift. Do not assume they will recover on their own.
Multi-product customer at different stages for different products	Maintain a journey per product but coordinate touchpoints. A single QBR should cover all products. The overall health score should reflect the aggregate.
Customer has no defined success metric	Work with the customer to define one before exiting onboarding. If they refuse, use proxy metrics (adoption depth, user activation rate). Document the gap as a risk.
Very large enterprise with multiple business units adopting independently	Treat each business unit as a semi-independent account with its own journey. Coordinate at the enterprise level for executive touchpoints, billing, and strategic alignment.
Customer in a regulated industry with slow procurement and legal cycles	Extend stage duration targets for Handoff and Onboarding. Front-load relationship building during the legal review period. Do not count legal delays against onboarding metrics.
Free-to-paid conversion customer (already using the product)	Compress or skip Onboarding and First Value stages. Begin at Adoption stage. Focus early touchpoints on paid-feature activation and value demonstration vs. basic setup.

customer-journey

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