Billing System Migration
As sole technical owner, migrated SalesRabbit's entire billing backbone from Recurly to Ordway — roughly 2,000 live subscriptions and 50,000 historical invoices — with zero disruption to customers.
Problem
One early morning in 2020, a SalesRabbit customer called in asking why their card had just been charged $15,000 — about 10x their normal bill. The calls kept coming. Some customers had been overbilled by as much as $15 million against typical bills in the low thousands of dollars, and hundreds of fraud alerts fired across the customer base. The cause was a data bug in that morning's billing script (it had calculated charges off lead count instead of user count), not a platform failure — but the days of refunds, subscription fixes, and root-cause digging that followed made clear how much trust and engineering rigor the billing system needed going forward.
That incident wasn't the reason SalesRabbit ultimately moved off Recurly, but it was a preview of the stakes. The real driver was accounting: Recurly had no native general-ledger integration, so revenue recognition, deferred revenue, and MRR/ARR reporting all required manual work downstream. Ordway, by contrast, could run as a sub-ledger feeding directly into QuickBooks and handle revenue recognition and GAAP-related automation natively. A secondary factor was API quality — Recurly's API supported only XML at the time, which made integration work slower and harder than it needed to be.
The scale made the switch high-risk: roughly 1,500-2,000 active customer subscriptions, about 5,000 inactive historical customer records, and roughly 50,000 historical invoices all had to move — along with the Salesforce and internal-app automations wired to them — without interrupting how customers experienced billing day to day.
Approach
Mickey was Operations Manager at the time — not yet a people manager — and served as the sole technical owner of the migration. He drove it through cross-functional coordination rather than direct authority: working with SalesRabbit's Salesforce admin on the integration, with Sales and Customer Success on new-customer handoff and training, and with the finance and executive team on MRR figures and customer segmentation during and after the transition.
Before committing, he reviewed Ordway's API directly to confirm it could support every automation the business needed. He then became SalesRabbit's in-house Ordway expert, a role he kept well past the migration itself.
The project ran on a roughly three-month execution window: sales conversations with Ordway started in August 2020, the decision to switch was made in late August/early September, and Ordway service began mid-September. He tested the migration on a handful of live customers first, then scaled up in batches through October and November, while new customers started onboarding directly into Ordway in October. The full existing customer base — including every connected Salesforce and internal-app automation — was fully migrated and functional in Ordway by November 2020, with a single company-wide parallel-run month rather than a rolling per-batch cutover.
Each batch followed the same discipline: migrate the data into Ordway, verify it was accurate, and only then turn that customer's service off in Recurly. He was careful about the timing of data pulls and uploads to avoid importing stale records — for example, a customer who canceled between download and upload. He didn't personally migrate payment methods, instead supporting the finance team on that piece, and he trained the Customer Success team on the new tool as part of the rollout.
Technical depth
- Reviewed Ordway's API up front to validate it could support all required automation before recommending the switch.
- Modeled the Ordway Subscription object carefully, since it set the cadence and amount for every recurring invoice going forward.
- Used Tray to run bulk API requests for creating customer and subscription records, including custom per-customer configuration such as unique discounts and pricing.
- Migrated ~50,000 historical invoices and ~5,000 inactive customer records, not just active ones, so Ordway could serve as a full system of record with meaningful reporting from day one.
- Linked new Ordway records to their corresponding Salesforce objects and connected subscriptions to SalesRabbit's internal app so they auto-updated as customers added or removed users and add-on products.
- Built (with Ordway's implementation team) and later independently maintained and extended an Ordway → BigQuery ETL pipeline, adding objects and adjusting schema as needed — infrastructure that went on to support heavier downstream reporting work.
Outcome
Migrated roughly 1,500-2,000 active subscriptions, ~5,000 inactive customer records, and ~50,000 historical invoices from Recurly to Ordway in about three months, with no interruption to the customer billing experience — customers simply started seeing invoices from Ordway instead of Recurly.
By the finance team's account (Mickey wasn't on the accounting side and didn't personally close the books), Ordway's native QuickBooks sub-ledger integration helped shrink month-end close from roughly 1.5-2 weeks down to about 3-5 days.
The Ordway → BigQuery pipeline he built and maintained became core data infrastructure for later reporting work, including the daily revenue reporting system described elsewhere on this site.
Became SalesRabbit's in-house Ordway expert and continued to own the platform going forward.