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Understanding Milestones

Milestones (also called phases) are sequential stages in your customer onboarding journey. They provide structure, set expectations, and enable progress tracking. [SCREENSHOT: Timeline view showing multiple milestones in sequence] Caption: Milestones give customers a clear roadmap from kickoff to go-live

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Anatomy of a Milestone

Each milestone has several components:

Name & Sequence

Descriptive name and order in the journey

Duration Estimate

Expected days to complete this phase

Dual Descriptions

What CSM team does vs what customer does

Actions

Specific tasks that happen during this phase

Status

pending, in_progress, completed, blocked

Exit Criteria

What must be done before moving to next phase

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Milestone Structure Best Practices

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1. Use 3-7 Milestones

Too few (1-2):
  • Not enough granularity
  • Hard to track progress
  • Customers feel lost
Just right (3-7):
  • Clear phase boundaries
  • Trackable progress
  • Manageable scope
Too many (10+):
  • Over-complicated
  • Phase fatigue
  • Administrative overhead
Start with 3-5 milestones for your first template. Add more only if there are natural breakpoints.

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2. Sequential, Not Parallel

Milestones should follow a linear path: 
Kickoff → Setup → Testing → Training → Launch
Not: 
        ├── Setup Track 1
Kickoff ├── Setup Track 2 → Testing → Launch
        └── Setup Track 3
If you have parallel work streams, use multiple actions within a single milestone rather than parallel milestones.

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3. Clear Entry and Exit Criteria

Each milestone should have: Entry Criteria (what must be true to start):
  • Previous milestone completed
  • Required inputs received
  • Stakeholders aligned
Exit Criteria (what must be true to complete):
  • All actions done
  • Deliverables approved
  • Customer ready for next phase
[SCREENSHOT: Milestone with entry/exit criteria displayed] Caption: Clear criteria help CSMs know when to progress

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Common Milestone Structures

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Simple SaaS (4-6 weeks)

1. Kickoff (Week 1)
   - Welcome & orientation
   - Gather requirements
   - Set expectations

2. Configuration (Weeks 2-3)
   - Platform setup
   - Data import
   - Integrations configured

3. Training (Week 4)
   - Admin training
   - User training
   - Documentation provided

4. Launch (Weeks 5-6)
   - Soft launch
   - Full rollout
   - Post-launch support

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Enterprise Implementation (12-16 weeks)

1. Project Kickoff (Weeks 1-2)
   - Stakeholder alignment
   - Project charter
   - Communication plan

2. Discovery & Requirements (Weeks 3-4)
   - Current state analysis
   - Requirement gathering
   - Solution design

3. Technical Setup (Weeks 5-7)
   - Infrastructure provisioning
   - Integration development
   - Security configuration

4. Data Migration (Weeks 8-9)
   - Data cleansing
   - Migration scripts
   - Validation testing

5. UAT & Testing (Weeks 10-11)
   - Test scenario execution
   - Bug fixes
   - Performance tuning

6. Training & Enablement (Week 12)
   - Train-the-trainer
   - End user training
   - Documentation

7. Staged Rollout (Weeks 13-15)
   - Pilot group
   - Department rollouts
   - Full company rollout

8. Stabilization (Week 16)
   - Post-launch support
   - Issue resolution
   - Optimization

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Self-Serve Activation (2-3 weeks)

1. Getting Started (Days 1-3)
   - Account setup
   - First use case
   - Quick win

2. Expansion (Days 4-7)
   - Additional features
   - Team invites
   - Integrations

3. Full Adoption (Days 8-21)
   - Advanced features
   - Workflow optimization
   - Success metrics

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Dual Perspective: CSM vs Customer

Every milestone should clearly show what both sides are doing.

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CSM Perspective (“What we’re doing”)

Behind-the-scenes work customers don’t see:
  • Platform configuration
  • Integration setup
  • Account provisioning
  • Internal coordination
Getting ready for customer interactions:
  • Preparing materials
  • Scheduling resources
  • Pre-work completion
  • Quality checks
Customer-facing activities:
  • Training sessions
  • Review meetings
  • Documentation delivery
  • Support provision
Ensuring quality and readiness:
  • Testing functionality
  • Reviewing submissions
  • Validating configurations
  • Approving go-live

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Customer Perspective (“What you’re doing”)

What customers need to give you:
  • Requirements documents
  • Technical specifications
  • Access credentials
  • Business context
Choices customers must make:
  • Configuration preferences
  • Feature selections
  • Timeline approvals
  • Stakeholder sign-off
Training and knowledge transfer:
  • Attending sessions
  • Completing homework
  • Reviewing documentation
  • Practicing scenarios
Validation activities:
  • UAT participation
  • Feedback provision
  • Bug reporting
  • Acceptance criteria review
[SCREENSHOT: Side-by-side milestone description showing both perspectives] Caption: Dual descriptions align expectations on both sides

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Milestone Duration Estimation

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Factors Affecting Duration

Higher complexity = longer duration
  • Number of integrations
  • Custom development needed
  • Data migration volume
  • Stakeholder count
  • Technical architecture complexity

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Setting Realistic Durations

Base estimates on historical data: 
Look at your last 10 implementations:
- Kickoff: 5-7 days average
- Technical Setup: 14-21 days average
- Training: 7-10 days average
- Launch: 5-7 days average

Use median, not best-case!
Customers will hold you to your estimates. Better to under-promise and over-deliver than the reverse.

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Milestone Status Management

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Status Types

StatusMeaningWhen to Use
PendingNot started yetFuture milestones
In ProgressCurrently activeCurrent phase
CompletedAll doneFinished phases
BlockedStuck on issueRequires intervention

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Transitioning Between Statuses

1

Starting a Milestone

Trigger: Previous milestone completeActions:
  1. Verify previous milestone exit criteria met
  2. Confirm customer readiness
  3. Click “Start Milestone”
  4. Thread triggers milestone_start actions
  5. Notify customer of phase transition
[SCREENSHOT: Start milestone button and confirmation]
2

Progressing Through Milestone

During the phase:
  • Execute triggered actions
  • Monitor customer responses
  • Track completion percentage
  • Address blockers as they arise
  • Communicate progress
Status remains “In Progress”
3

Completing a Milestone

Trigger: All actions done + exit criteria metActions:
  1. Verify all actions completed
  2. Confirm exit criteria satisfied
  3. Get customer confirmation if needed
  4. Click “Mark Complete”
  5. Next milestone auto-starts (optional)
[SCREENSHOT: Complete milestone with completion checklist]
4

Blocking a Milestone

Trigger: Issue preventing progressActions:
  1. Click “Mark as Blocked”
  2. Add blocker description
  3. Assign owner to resolve
  4. Set expected resolution date
  5. Communicate to customer
[SCREENSHOT: Blocked milestone with blocker details]
Customers see blocked status in their portal. Be transparent about blockers and resolution plans.

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Advanced Milestone Techniques

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Conditional Milestones

For complex scenarios where path varies by customer: Example: Enterprise vs SMB 
All Customers:
├── Kickoff
└── Discovery

Then branches:
├── [Enterprise] → Architecture Design → Custom Development → UAT
└── [SMB] → Standard Setup → Quick Training → Launch
Currently, conditional milestones require creating separate templates. Multi-path support in a single template is on the roadmap!

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Milestone Groups

Organize related milestones into groups: 
Phase 1: Foundation (Weeks 1-4)
├── Kickoff
└── Requirements

Phase 2: Build (Weeks 5-10)
├── Development
├── Integration
└── Testing

Phase 3: Launch (Weeks 11-12)
├── Training
└── Go-Live
[SCREENSHOT: Grouped milestones in timeline view] Caption: Milestone groups provide high-level structure

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Parallel Actions Within Milestones

If multiple work streams happen simultaneously: Don’t create parallel milestones. Instead: 
Milestone: Technical Setup (Weeks 2-4)

Actions (can happen in parallel):
├── Platform Configuration (Track 1)
├── Integration Development (Track 2)
├── Data Migration Prep (Track 3)
└── Security Review (Track 4)
Use action delays to sequence when needed, but all within one milestone.

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Milestone Best Practices Summary

Keep It Simple

3-7 milestones, clear boundaries

Dual Perspectives

Show both CSM and customer work

Realistic Durations

Base on historical data, not hopes

Clear Criteria

Entry and exit criteria for each phase

Sequential Flow

Linear progression, not parallel

Meaningful Names

Descriptive, customer-friendly names

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Next Steps

Action Types

Learn about the five action types in detail

Best Practices

See proven milestone structures that work

Creating Templates

Build your first complete template

Implementation Tab

Manage milestone progress in accounts