lo-milestone-tracker

name	lo-milestone-tracker
description	Tracks customer progress against defined adoption and lifecycle milestones, flags blockers, and reports on time-to-milestone metrics. Use when asked to track customer milestones, monitor adoption progress, measure time-to-value, build success plans with measurable checkpoints, identify stalled accounts, report on adoption velocity, or when any workflow needs to know whether a customer is on track against their plan. Also triggers for questions about success planning, goal tracking, outcome measurement, or adoption milestones.
license	MIT
metadata	{"author":"Stephen Rogan","version":"1.0.0","pillar":"lifecycle-orchestration","category":"workflow-engine"}

Milestone Tracker

Tracks customer progress against defined adoption and lifecycle milestones. Flags blockers, measures time-to-milestone, and reports on adoption velocity. Operates across the full lifecycle, not just onboarding -- milestones exist from first login through mature expansion.

This is a tracking and alerting skill. It monitors progress against defined checkpoints and surfaces deviations. It does not define the milestones (that is a joint human exercise with the customer) or resolve blockers (that is human judgment).

When to Run

• Continuous: Monitors all accounts with active milestone plans against product analytics and CRM data
• Triggered: When product analytics detects a milestone completion event or when an expected milestone date passes without completion
• On-demand: When a CSM requests milestone status for a specific account

Milestone Framework

Milestone Types

Type	Definition	Example
Activation	First meaningful use of the product	First workflow completed, first report generated
Adoption	Sustained use of core capabilities	80% of team logging in weekly for 4 consecutive weeks
Depth	Advanced feature or use case adoption	Second use case live, API integration active
Outcome	Business result achieved through the product	20% reduction in manual process time, measurable ROI
Expansion	Growth beyond initial scope	New department onboarded, tier upgrade, additional product

Milestone Plans

Each account can have a milestone plan -- a set of defined milestones with target dates and success criteria. Plans can be:

• Template-based: Generated from segment defaults (e.g., all mid-market accounts get the standard adoption plan)
• Custom: Defined collaboratively by the CSM and customer during onboarding or QBR

Core Execution Logic

Step 1: Define or Load Milestone Plan

For each account:

1. Check if a custom milestone plan exists in CRM
2. If yes: load the plan with milestones, target dates, and success criteria
3. If no: apply the segment-default template (see references/milestone-templates.md)
4. Each milestone has: name, type, target date, success criteria (measurable), detection method (how the system knows it happened)

Step 2: Monitor Progress

For each active milestone:

1. Query the appropriate data source for the milestone's detection criteria
2. Classify status: Completed (criteria met), On Track (not yet due, progress visible), At Risk (due within 14 days, no progress), Overdue (past due date, criteria not met), Blocked (CSM has flagged a specific blocker)

Detection methods by milestone type:

Detection Source	Milestones Detected
Product analytics	Activation (first use), Adoption (usage thresholds), Depth (feature usage)
CRM data	Expansion (opportunity stage), custom milestones logged by CSM
Customer confirmation	Outcome milestones (business results -- requires CSM to confirm with customer)

Step 3: Flag Deviations

Condition	Action
Milestone at risk (due in 14 days, no progress)	Alert CSM: "Milestone [X] is due in [N] days with no progress detected"
Milestone overdue (past due, not complete)	Alert CSM + include in overdue report: "Milestone [X] is [N] days overdue"
Milestone completed ahead of schedule	Log completion, notify CSM (positive signal -- may indicate readiness for acceleration)
No milestone progress across the entire plan for 30+ days	Alert CSM: "No milestone progress for [account] in 30 days -- investigate stall"

Step 4: Measure Time-to-Milestone

For completed milestones, track:

• Actual completion date vs. target date (ahead, on time, late)
• Time from prior milestone to this milestone (velocity)
• Comparison to segment benchmark (how fast vs. peers)

Step 5: Generate Milestone Report

Per-account milestone status:

{
  "account_id": "string",
  "plan_type": "custom",
  "milestones": [
    {
      "name": "Core workflow live",
      "type": "activation",
      "target_date": "2026-03-15",
      "status": "completed",
      "completed_date": "2026-03-10",
      "days_ahead": 5
    },
    {
      "name": "80% team adoption",
      "type": "adoption",
      "target_date": "2026-04-15",
      "status": "on_track",
      "progress_indicator": 
    
    
       
       
       
       
       
    
  
   
          

Portfolio milestone report (weekly):

• Milestones completed this week (by account and type)
• Milestones overdue (by account, days overdue, blocker if known)
• Stalled accounts (no progress in 30+ days)
• Time-to-milestone benchmarks (average by type and segment)

Handoff to Human

Decision Point	Context Provided	What the Human Decides
Milestone plan creation	Segment template, customer goals from onboarding	Which milestones to set, what timelines are realistic, how to define success criteria
At-risk milestone	Milestone details, progress data, last touchpoint	Whether to intervene proactively, adjust the timeline, or investigate the blocker
Overdue milestone	Overdue details, account health, engagement data	Whether to push the customer, adjust the plan, escalate, or accept the delay
Stalled account	30-day stall, usage data, last CSM interaction	Root cause investigation -- is this disengagement, a priority shift, or a technical blocker?
Outcome milestone confirmation	Usage data, suggested outcomes	Whether the customer has actually achieved the business result (requires customer conversation)

Confidence and Limitations

• High confidence for activation and adoption milestones detected via product analytics -- measurable and objective
• Medium confidence for progress estimation on milestones not yet due (trending indicators)
• Low confidence for outcome milestones -- business results require customer confirmation, not just usage data
• Cannot detect blockers that exist outside observable data (e.g., customer's internal priority shifted, budget was reallocated)
• Template-based plans may not fit every account. Custom plans require CSM effort to define but produce more meaningful tracking

Dependencies

Required:

• Product analytics (for activation and adoption milestone detection)
• CRM API (milestone plan storage, status tracking)

Strongly recommended:

• lo-onboarding-orchestrator (for onboarding milestone handoff)
• bi-usage-monitor (for progress indicators on usage-based milestones)
• bi-health-score (for health context on stalled accounts)

References

• references/milestone-templates.md -- Segment-default milestone plan templates