Teams at Upside

Own the strategy, roadmap, and growth of Upside’s restaurant vertical. Adapt incrementality measurement and offer optimization to restaurant economics, build merchant-facing reporting and onboarding products, and drive partner adoption, retention, and profitability. Partner with engineering, data science, design, sales, account management, and marketing while making integration decisions across POS, payments, and data systems. Establish OKRs and lead a 0-to-1 business area without direct authority.

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.