Lo onboarding orchestrator

Onboarding Orchestrator

Manages the end-to-end onboarding workflow for new customers. Sequences tasks, triggers milestone-based communications, tracks completion against timeline, and flags delays or blockers for human intervention. Part of the Lifecycle Orchestration pillar -- the highest-volume workflow in most CS organisations.

This is an execution and tracking skill. It runs the onboarding process -- scheduling tasks, sending templated communications, updating CRM fields, and monitoring progress. It hands off to the human at defined decision points: when the customer deviates from the expected path, when a blocker requires judgment, or when the kickoff call needs to be led.

When to Run

• Triggered: When a new deal closes and the handoff from sales is initiated (CRM opportunity stage = Closed Won)
• Continuous: Once activated for an account, runs until the onboarding workflow reaches the "first-value milestone" or is manually closed
• On-demand: When a CSM requests onboarding status or needs to reset/restart an onboarding workflow

Onboarding Workflow Structure

The onboarding workflow is a sequence of phases, each containing tasks with defined triggers, owners, and completion criteria. The skill executes AGENT tasks automatically and surfaces HUMAN tasks with context and deadlines.

Phase 1: Handoff and Setup (Days 0-3)

Task	Operator	Trigger	Completion Criteria
Generate handoff brief from sales data	AGENT	Deal closes	Brief created with deal context, customer expectations, technical requirements, key contacts
Create onboarding project in CRM	AGENT	Deal closes	Project record created with all fields populated, timeline set
Send welcome email to primary contact	AGENT	Handoff brief approved by CSM	Email sent using segment-appropriate template with personalisation
Schedule kickoff call	AGENT	Welcome email sent	Calendar invite sent to customer contacts + CSM + relevant internal stakeholders
Prepare kickoff deck	AGENT	Kickoff call scheduled	Deck generated with account context, agenda, expected outcomes, timeline
Lead kickoff call	HUMAN	Call scheduled	CSM leads the call, sets expectations, confirms goals and timeline

Phase 2: Technical Activation (Days 3-14)

Task	Operator	Trigger	Completion Criteria
Provision account and configure environment	AGENT	Kickoff complete	Account provisioned per technical requirements from handoff brief
Send configuration guide to customer	AGENT	Environment provisioned	Guide sent with step-by-step instructions tailored to customer's use case
Track configuration completion	AGENT	Guide sent	Monitor product analytics for configuration milestones; flag if incomplete after 5 business days
Send check-in email at Day 7	AGENT	Day 7 from kickoff	Templated check-in asking about configuration progress, offering help
Resolve configuration blockers	HUMAN	Blocker flagged by tracking or customer	CSM investigates and resolves -- may involve support, product, or direct guidance

Phase 3: Adoption and First Value (Days 14-45)

Task	Operator	Trigger	Completion Criteria
Track first use-case completion	AGENT	Configuration complete	Monitor product analytics for core workflow execution; flag if no activity after 7 days
Send adoption tips email sequence	AGENT	First login detected	3-email sequence over 14 days: getting started, advanced tips, success stories
Schedule 30-day check-in call	AGENT	Day 25 from kickoff	Calendar invite to primary contact + CSM
Generate 30-day progress report	AGENT	Day 28 from kickoff	Report with usage metrics vs. onboarding plan, adoption milestones hit/missed
Lead 30-day review call	HUMAN	Call scheduled	CSM reviews progress, adjusts adoption plan, identifies expansion of scope
Declare first-value milestone	HUMAN	Evidence of value realisation	CSM confirms the customer has achieved their primary use case. Onboarding complete

Phase 4: Transition to Steady State (Days 45-60)

Task	Operator	Trigger	Completion Criteria
Update account lifecycle stage in CRM	AGENT	First-value declared	Stage changed from "Onboarding" to "Adopted"
Generate onboarding summary	AGENT	Stage change	Summary document: timeline, milestones, blockers encountered, CSM notes
Transition to steady-state check-in cadence	AGENT	Stage change	Onboarding cadence deactivated; steady-state cadence activated via lo-check-in-scheduler
Send onboarding completion email	AGENT	Stage change	Email to customer confirming successful onboarding, introducing ongoing support model

See references/onboarding-templates.md for all email templates and deck formats referenced above.

Delay Detection and Escalation

The skill monitors elapsed time at every task and flags delays:

Delay Condition	Action
Task not completed within expected timeframe + 2 business days	Internal flag to CSM: "Task [X] is overdue by [N] days"
Customer-dependent task stalled for 5+ business days	Automated nudge email to customer (configurable, can be disabled)
Phase not completed within expected timeframe + 5 business days	Escalation flag to CSM + manager: "Onboarding for [account] is behind schedule"
No product activity detected 10+ days post-kickoff	Alert CSM: "No usage detected -- investigate whether technical blocker exists"

Delay detection is automated. Delay resolution is HUMAN -- the CSM decides whether to push, adjust the timeline, or escalate.

Output Format

Onboarding status record (per account):

{
  "account_id": "string",
  "onboarding_start": "2026-03-01",
  "current_phase": "phase_2_technical_activation",
  "days_in_onboarding": 10,
  "expected_completion": "2026-04-15",
  "tasks_completed": 8,
  "tasks_remaining": 7,
  "tasks_overdue": 1,
  "overdue_details": [
    { "task": "Configuration completion", "expected_by": "2026-03-08", "days_overdue": 2, "owner": "customer" }
  ],
  "next_agent_action": { "task": "Send Day 7 check-in email", "scheduled": "2026-03-08" },
  "next_human_action": { "task": "Resolve configuration blocker", "urgency": "this_week" },
  "health_indicators": {
    "product_activity_detected": true,
    "customer_responsive": true,
    "on_track": false,
    "risk_level": "low"
  }
}

Handoff to Human

Decision Point	Context Provided	What the Human Decides
Kickoff call	Handoff brief, deck, customer expectations	How to frame the engagement, which goals to prioritise
Configuration blocker	Blocker details, days stalled, customer communications	Whether to troubleshoot directly, involve support, or adjust scope
30-day review	Progress report, usage data, milestone status	Whether onboarding is on track, whether to adjust the plan
First-value declaration	Usage evidence, customer feedback, adoption metrics	Whether the customer has achieved sufficient value to transition to steady state
Onboarding at risk	Delay escalation data, customer engagement pattern	Whether to extend onboarding, escalate internally, or accept the pace

Confidence and Limitations

• High confidence for task sequencing, scheduling, and tracking -- these are deterministic workflows
• Medium confidence for delay detection -- the system knows tasks are late but not why
• Cannot assess whether the customer is satisfied with the onboarding experience (that requires human interaction)
• Cannot adapt the onboarding plan to customer-specific circumstances without human input (e.g., customer wants to skip Phase 2 because they have internal technical resources)
• Template communications work for standard onboarding. Complex enterprise onboarding may require fully custom communications written by the CSM

Dependencies

Required:

• CRM API (deal data for handoff, project tracking, lifecycle stage management)
• Calendar integration (scheduling kickoff and check-in calls)
• Email integration (sending templated communications)
• Product analytics (tracking configuration completion, first usage, adoption milestones)

Optional:

• lo-handoff-manager (for generating the sales-to-CS handoff brief)
• bi-health-score (for onboarding health indicators)
• lo-milestone-tracker (for detailed milestone tracking beyond the onboarding scope)
• Document generation (for kickoff decks and progress reports)

References

• references/onboarding-templates.md -- Email templates, deck structure, and report formats
• references/segment-variations.md -- How the onboarding workflow adapts by segment (enterprise vs. mid-market vs. SMB)