UpsideVerified Source

Engineering Manager, Reconciliation & Transaction Pipeline

207K–237K
Partially · Chicago, Illinois
Posted August 12, 2026
payroll

Overview

You'll lead the Reconciliation team at Upside, owning the transaction-matching pipeline that powers cash-back verification and post-claim experiences. This full-stack team spans Kotlin Multiplatform (KMP) front-ends and Python + Java back-ends, processing billions in annual commerce. You'll coach 6-8 engineers, drive technical strategy, and partner with Product, Design, and Data to scale systems that determine cash-back outcomes. This hybrid role is based in Austin, Chicago, DC, or NYC with in-office days on Monday, Tuesday, and Thursday.

What You'll Do7

  • 1Define the team's domain for offer reconciliation, post-claim consumer experiences, receiptful/receiptless flows, and self-heal capabilities, adapting as Upside grows.
  • 2Champion quality across the reconciliation stack, focusing on accuracy, reliability, observability, and scalability in systems that determine cash-back outcomes.
  • 3Keep the platform secure and production-ready with tooling and practices that make iteration safe and diagnosis fast, using AWS and Snowflake.
  • 4Act as a player-coach, contributing hands-on in high-leverage areas while guiding execution and modeling smart use of generative AI to speed up development and debugging.
  • 5Partner cross-functionally with Product, Design, Data, and Consumer Ops to tie roadmap and strategy to gains in transaction success and user trust.
  • 6Build a safe, collaborative team where problems are named openly and discussion leads to the best work.
  • 7Coach engineers, recognize wins, and help them build skills that serve them for years, fostering growth and independence.

Requirements7

  • 13+ years of engineering management experience, with mobile or distributed API domains as a strong plus.
  • 2A track record of scaling teams and leveling up systems, even when the path forward is unclear.
  • 3Comfort going deep on technical challenges across mobile and API infrastructure, with AWS a plus.
  • 4Hands-on familiarity with back-end data tools such as Snowflake and Hex.
  • 5Knowledge of mobile and API development patterns: serverless, event-driven, REST, microservices, MVI, and Clean Architecture is a plus.
  • 6A bias toward clarity over consensus, especially in fast-moving situations.
  • 7Genuine curiosity about generative AI as a tool for improving how your team builds and ships.

Salary Insight

$207 - $237k per year

Location

Typepartially
LocationChicago, Illinois

Required Skills

Kotlin MultiplatformPythonJavaAWSSnowflakeHexServerlessEvent-drivenRESTMicroservicesMVIClean ArchitectureGenerative AI
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