Case study 06 · Payments & POS
Owned the CAKE POS payment gateway product as Proxy Product Owner from 2017–2019, building on 5 years in operations and support on the same product. The clearest example of the operator-then-builder move: the support data I generated became the product team's prioritization.
Before owning the product, I spent five years in operations and support on CAKE POS - progressing from Application Support Engineer providing tier 1 and 2 support to Operations Lead on the payment gateway, building the support team from scratch. That tier-level visibility into how the product actually failed in the field generated the data that grounded the product team's prioritization. When I moved into the Proxy Product Owner role, I wasn't starting from a roadmap; I was starting from years of knowing exactly where the product broke.
As Proxy Product Owner I owned the CAKE POS payment gateway end-to-end: identifying issues through support data, coordinating with third-party processors, and shipping improvements. Over the role I doubled the number of payment gateway users and grew revenue 120% ($40M).
I noticed an unusual number of chargebacks being lost and started digging. The root cause wasn't a volume problem or slow response times - it was a design mismatch. The statuses the third-party processor sent for chargeback state changes weren't being interpreted correctly by the internal system. The internal workflow didn't map to how chargebacks actually work in the US. Cases were being mishandled at each status transition, and winnable disputes were being abandoned as a result.
I studied how the chargeback process actually worked end-to-end - the status lifecycle, the evidence windows, the processor's expectations at each stage - and redesigned the entire chargeback handling system at CAKE to match it. The $50K/month in savings came from winning chargebacks that had previously been abandoned: cases that were defensible but were being lost because the system was misreading where each dispute stood.
Seven years in payments and POS - gateway revenue, third-party processor coordination, and chargeback investigation - is a genuine differentiator for B2B fintech. It maps directly to payments infrastructure, embedded finance, and the operational workflows that sit underneath B2B lending and SME platforms.