Transforming a Legacy Enterprise Platform
Financial services software — 200 employees — Chicago, IL
The Challenge
A 200-person Chicago-based financial services software company had been running its products on a managed colocation facility for over seven years. The infrastructure was expensive, difficult to scale, and increasingly incompatible with the company's growth ambitions. Leadership had committed to migrating to AWS before year-end — but were concerned about three things: customer disruption, system-level compliance requirements under SOC 2 and PCI DSS, and the risk of timeline overrun.
The existing environment included 140+ virtual machines, 23 production databases (a mix of SQL Server, PostgreSQL, and MySQL), several legacy message queuing systems, and a patchwork of bespoke deployment scripts. No cloud expertise existed inside the organization.
Our Approach
Skygate Advisors began with a comprehensive 3-week discovery and Well-Architected alignment assessment. We categorized every workload against a migration strategy (the 6 Rs), mapped all data flows, and coordinated directly with the client's external compliance auditor to ensure migration activities would not trigger a re-audit cycle.
We designed a wave-based migration plan: non-production environments first, then lower-risk production workloads, with the most sensitive financial processing systems last. Each wave included a deployment window, parallel-run period, validation gate, and tested rollback procedure. The AWS Migration Hub was used for centralized tracking.
The Results
The full migration was completed in 4 months — two weeks ahead of the contractual deadline. Throughout the process, the client maintained 99.97% uptime across all customer-facing services. There were zero compliance incidents, and the client's SOC 2 Type II report contained no material findings related to the migration.
The new AWS architecture reduced monthly infrastructure spend from $155K to $103K — a 34% reduction and $620K in annual savings. The client's engineering team was left fully capable of operating the environment independently, with documented runbooks, Architecture Decision Records, and a 40-hour knowledge transfer program included in the engagement.
“Skygate Advisors didn't just execute a migration. They transformed how we think about infrastructure. Two years later, our engineers are still using the patterns they taught us.”
— VP of Engineering, Financial Services Client
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