Lo Milestone Tracker

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

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:

Step 3: Flag Deviations

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": "62% of team active, trending up"
    },
    {
      "name": "ROI measurement",
      "type": "outcome",
      "target_date": "2026-06-15",
      "status": "not_started",
      "progress_indicator": "Requires customer input -- not yet requested"
    }
  ],
  "overall_velocity": "ahead_of_plan",
  "next_milestone_due": { "name": "80% team adoption", "due": "2026-04-15", "days_remaining": 36 }
}

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

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