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Chapter 09 of 11

30-60-90 Day Customer Training Rollout Plan

Use this rollout plan to move from scattered resources to a structured customer training program.

Days 1-30: Diagnose and Prioritize

Goal: Identify the highest-impact training opportunities.

Actions

  • Interview customer success, support, product, sales, and implementation teams.
  • Review top customer questions and support tickets.
  • Identify the customer lifecycle stages with the most friction.
  • Define target audiences and roles.
  • Audit existing training content.
  • Choose 3-5 business outcomes to support.
  • Prioritize the first learning path.

Deliverables

  • Customer training audience map
  • Content inventory
  • Top friction points list
  • First curriculum outline
  • Measurement plan
  • Ownership model

30-Day Success Criteria

By day 30, you should know:

  • Who the training is for
  • What problem it solves
  • Which content already exists
  • What must be built first
  • How success will be measured

Days 31-60: Build the Minimum Viable Program

Goal: Launch a focused training experience for one priority audience or lifecycle stage.

Actions

  • Build the first customer learning path.
  • Create or convert 3-6 core modules.
  • Add one quick-reference playbook.
  • Create a customer onboarding checklist.
  • Set up a live Q&A or office-hours event.
  • Define completion and feedback tracking.
  • Train internal customer-facing teams on how to promote the program.

Deliverables

  • First customer learning path
  • Core onboarding course
  • Customer admin checklist
  • Troubleshooting playbook
  • Live event plan
  • Feedback form
  • Internal launch guide

60-Day Success Criteria

By day 60, customers should be able to access a structured learning experience instead of scattered resources.

Days 61-90: Launch, Measure, and Improve

Goal: Launch the program, collect data, and improve based on customer behavior.

Actions

  • Launch to a pilot customer segment.
  • Track enrollment, completion, feedback, and drop-off.
  • Compare support questions before and after launch.
  • Collect feedback from customer success managers.
  • Identify content gaps.
  • Add role-based follow-up modules.
  • Prepare a leadership impact summary.

Deliverables

  • Pilot results summary
  • Content improvement backlog
  • Engagement report
  • Support ticket insight summary
  • Next-phase curriculum plan
  • Leadership update

90-Day Success Criteria

By day 90, you should be able to answer:

  • Are customers using the training?
  • Which content is most valuable?
  • Where do learners drop off?
  • What questions remain unresolved?
  • What should be built next?
  • What early business impact is visible?
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