Payments & Infrastructure
Migrating an Entire Subscription Base With Zero Errors
Led the strategic migration of the company's entire subscription base from three fragmented legacy systems into a single source of truth.
The Challenge
Three legacy billing systems had accumulated years of technical complexity. Each had its own data model, logic, and vendor dependencies, and none spoke to each other. For a company where subscriptions were the core revenue stream, there was zero tolerance for errors. Every decision carried outsized financial risk.
The Approach
In a product leadership role, I led the initiative strategically from initiation through full migration alongside the Head of Engineering and a dedicated Product Manager. We designed a phased migration plan with parallel-running periods, automated reconciliation, and system-gated cutovers. Each phase was sequenced by risk level, with the most complex, long-standing subscriptions handled last. We worked with leading SaaS providers in the billing and payments space to ensure the target system could handle the full range of inherited edge cases.
The Outcome
Every single subscription migrated without error. Three legacy systems were fully decommissioned. The business now operates from one authoritative billing platform, giving Finance, Support, and Product a shared view of subscription state for the first time and laying the foundation for future pricing and packaging capabilities.
This kind of work usually runs as interim Head of Product.
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