Project Background
FinSight, a mid-market financial analytics company, runs its customer reporting platform on on-prem infrastructure that is nearing capacity. Leadership wants to migrate the platform to AWS to improve scalability, reduce incident volume, and support two enterprise deals that require cloud-based disaster recovery. You are the program manager leading the migration across engineering, security, data, and customer operations.
The core team includes 10 people: 4 platform engineers, 2 data engineers, 1 security engineer, 1 SRE, 1 product manager, and you. The CEO has asked for customer-facing migration completion within 16 weeks because the sales team has committed cloud-readiness to prospects by quarter end.
Key Stakeholders
The CTO wants a fast migration to unlock infrastructure savings this fiscal year. The Head of Security requires full IAM hardening, encryption, and audit logging before any production cutover. The VP of Customer Success wants zero disruption for the top 20 accounts during month-end reporting. The Data Engineering manager is concerned that her team is already committed to a separate warehouse upgrade.
Constraints
- Budget remaining: $180,000 for cloud setup, external consulting, and migration tooling
- Timeline: 16 weeks with no approved headcount increase
- Current platform load: 1,200 daily active business users and 7 TB of reporting data
- Allowed customer downtime during cutover: maximum 2 hours
- Security review must be completed by Week 8 to stay on schedule
Complications
- One of the four platform engineers is leaving in Week 6, with most knowledge of the legacy scheduler.
- AWS networking approval from the central IT team typically takes 3 weeks, but your project plan only has 10 business days of slack.
- Sales is asking whether the top 5 enterprise customers can be migrated 4 weeks early as a proof point.
Your Task
- Build a 16-week execution plan with phases, dependencies, and decision points.
- Recommend how to sequence pilot customers, full migration, and rollback readiness.
- Define success metrics for launch and the first 30 days after cutover.
- Identify the top risks and mitigation actions, including staffing and security dependencies.
- Explain the trade-offs between an all-at-once migration and a phased rollout.
