Work

Situation: Migrating from flat tiers to seat-plus-usage hybrid. Multiple grandfathered enterprise contracts with custom terms.

Action: Identified 7 grandfathered contract patterns that would have caused billing disputes. Mapped entitlement drift across 3 systems. Delivered remediation plan with sequenced rollout.

Outcome: Client engineering team executed migration in 6 weeks. No customer escalations during the transition.

Situation: Stripe and Salesforce showed different ARR numbers. Finance team spending 2 days per month on manual reconciliation. Audit approaching.

Action: Traced drift to 4 root causes: webhook failures, manual CRM overrides, timezone mismatches in renewal dates, and a legacy discount structure not reflected in Stripe metadata.

Outcome: Delivered reconciliation playbook. One-time cleanup completed in 3 weeks. Monthly reconciliation reduced from 2 days to 2 hours with automated checks.