Leads the Merchant & Pay engineering organization, overseeing managers and teams responsible for merchant, partner, payment, and internal tooling systems. Owns technical strategy, multi-year roadmaps, reliability, scalability, security, engineering standards, and generative AI adoption. Partners with Product, Data, Security, and company leadership while recruiting, developing, and retaining engineering talent. Requires extensive engineering leadership experience, AWS expertise, marketplace or payments experience, and experience scaling business-critical platforms.

Lead a full-stack Reconciliation team owning transaction-matching pipelines across mobile and backend systems. Drive reliability, observability, and accuracy for post-claim flows, coach and grow engineers, contribute hands-on in high-leverage technical areas, partner cross-functionally, and scale systems and processes to improve transaction success and user trust.

The role involves designing and building AI-native systems for revenue teams at Upside, including developing applications, partnering with teams, managing the entire stack, and improving system reliability and performance.