A CTO to steady a payments scale-up through a platform rebuild

The brief

The company processes card and account-to-account payments for around 3,000 merchants in North America. Its founding CTO had moved into a chief architect role, and the engineering team of 140 had been reporting to a co-founder with a commercial background for most of a year. Meanwhile the core ledger, written in the company’s first months, was struggling with volume, and two large merchants had raised concerns about settlement delays.

The board wanted a CTO who had led a ledger or core banking migration at scale, who could manage a team spread across New York, Toronto and Lisbon, and who would be credible with banking partners and regulators. They also wanted someone who would work well with the founding CTO, who was staying.

The search

Marcus mapped 186 engineering leaders across payments, banking infrastructure and high-volume consumer platforms. Of the 52 we approached, 29 agreed to a first conversation. We were open with each of them about the state of the ledger, because anyone who joined without knowing would leave within a year.

Four reached the shortlist. Each spent half a day with the engineering leadership team working through a real incident from the previous quarter, and a technical assessor from our network reviewed their proposed approach to the migration. The near miss came late. The leading candidate’s partner had accepted a job in Chicago, and for ten days it looked as though the move would fall through. We worked with the company to agree a hybrid arrangement for the first six months, with a fixed schedule of weeks in New York, and the candidate signed on day 47.

The outcome

The new CTO reorganised engineering into four product-aligned groups within ninety days and brought in a head of platform, also placed by Roster. The ledger migration ran in phases over seven months and completed without a single settlement outage, holding 99.99% uptime throughout. Ten months on, settlement times have fallen by 40%, both of the unhappy merchants have renewed, and engineering attrition is at its lowest since the company was founded. The founding CTO calls it the best working partnership of their career.