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Salary: USD 188,000 - 237,000 / annual
Upside is transforming brick-and-mortar commerce by bringing online retail sophistication—profit measurement, attribution, incrementality—to physical retail. The platform helps millions of consumers earn 2-3x more cashback and hundreds of thousands of retailers acquire profitable customers. Billions in commerce flow through Upside annually.
You'll lead the Reconciliation team, a full-stack group owning Upside's transaction-matching pipeline and post-claim experience. The team spans Kotlin Multiplatform (KMP) mobile front-end and Python + Java back-end, responsible for accurate transaction verification, cashback award logic, and user recovery flows.
Key responsibilities:
- Build and scale a safe, collaborative team of 6-8 engineers with a player-coach mindset, contributing hands-on in high-leverage areas
- Define and evolve the team's domain: offer reconciliation, post-claim consumer experiences, receiptful/receiptless transaction flows, and self-heal capabilities
- Champion quality across the reconciliation stack: accuracy, reliability, observability, scalability, and clear decision-making in systems determining cashback outcomes
- Ensure platform security, resilience, and production-readiness with safe iteration and fast diagnosis practices
- Partner cross-functionally with Product, Design, Data, Consumer Ops, and external partners to tie roadmap and strategy to transaction success and user trust
- Raise engineering standards in quality, performance, speed, and technical practices
- Coach engineers, recognize wins, and help build skills for long-term growth
You'll combine technical depth with people-first leadership, operating with a first-team mindset and bringing clarity over consensus, especially in fast-moving environments. The role requires comfort going deep on technical challenges across mobile and API infrastructure (AWS experience a plus) and back-end data tools (Snowflake, Hex). Hands-on familiarity with mobile and API patterns—serverless, event-driven, REST, microservices, MVI, Clean Architecture—is valuable. Genuine curiosity about generative AI as a development tool is expected.
This is a hybrid role based in Austin, Chicago, DC, or NYC with required in-office attendance Monday, Tuesday, and Thursday.
