1.Software migration with a hard deadline
When it fits: Use this when a system has to move before a fixed business date, the old system keeps running in the meantime, and the riskiest part is data nobody has looked at in years.
Billing migration to Stripe Billing
Owner: Hannah Weiss (engineering) Sponsor: Marcus Lee (CFO) Start: 2026-10-05 Target finish: 2027-01-22 Last updated: 2026-10-27 Status: At risk (proration test results due Nov 6) Related: [[Billing migration brief]], [[Platform team]]
Objective
Move all 2,300 paying customers from the in-house invoicing system to Stripe Billing before annual renewals start on Feb 1, 2027, so finance stops reconciling invoices by hand.
Success measures:
- Manual invoice corrections: from about 140 a month to under 10 by March 2027
- Zero customers double-charged during cutover
Scope
- In scope: subscriptions, invoices, card payments, dunning emails, the finance export
- Out of scope: multi-currency (removed Oct 20, see changes), purchase-order customers (38 accounts, stay on manual invoicing until Q2)
Milestones
- Customer and plan data exported and cleaned (@Hannah) @done(2026-10-23)
- Proration matches the old system for the 12 test scenarios (@Diego) @due(2026-11-06)
- Pilot: 100 monthly customers billed by Stripe (@Hannah) @due(2026-12-01)
- Finance signs off on December reconciliation (@Marcus) @due(2027-01-08)
- All remaining customers cut over, old system read-only (@Hannah) @due(2027-01-22)
Resources
- People: Hannah (60 percent), Diego (full time), Ana from finance (one day a week)
- Budget: $24,000 for a contractor to write the data migration scripts, approved by Marcus
- Tools and access: Stripe test and live accounts, read access to the billing database
Dependencies
- Support macros for billing questions, ready before the pilot (contact: Ravi, support)
Risks
- Proration differs from the old system. Likelihood: medium. Impact: customers see unexpected amounts on upgrade. Mitigation: run all 12 scenarios side by side before the pilot (@Diego)
- Old card tokens fail to migrate. Likelihood: low. Impact: failed renewals in February. Mitigation: migrate tokens in the pilot first and measure the failure rate (@Hannah)
Communication
- Status updates: Friday written update to Marcus and the support lead
- Decisions: scope or date changes go to Marcus, in writing, in the Friday thread
Changes to this plan
- 2026-10-20: Multi-currency removed from scope. Only 41 customers pay in EUR, and supporting it added four weeks. Approved by Marcus.