Engineering Manager, Reconciliation & Cash-Back Systems

Upside; Chicago (IL); Hybrid; USD 188,000 - 220,000; Full time

Benefits offered by this job

Medical, dental, and vision coverage

Equity (ISOs)

401(k) program

Parental leave

Flexible work environment

Learning and Development stipend

Transparent culture

Wellness programs

Job summary

Upside is seeking an Engineering Manager to lead the Reconciliation team, a full-stack group responsible for the transaction-matching pipeline spanning Kotlin Multiplatform front-end and Python/Java back-end.

You will drive quality, scale systems, and coach engineers while partnering with Product, Data, and Operations to improve cash-back accuracy and user trust. This role blends hands-on leadership with strategic direction in a hybrid, multi-city setting.

Qualifications

• 3+ years of engineering management experience, mobile or distributed API domains are a strong plus, but we care most about your leadership track record.
• Track record of scaling teams and leveling up systems, even when the path forward is unclear.
• Comfort going deep on technical challenges across mobile and API infrastructure (AWS a plus) and back-end data tools (Snowflake, Hex, and similar).
• Hands-on familiarity with mobile and API development patterns: serverless, event-driven, REST, microservices, MVI, Clean Architecture is a plus; we're happy to help you build on what you already know.
• A bias toward clarity over consensus, especially when things are moving fast.
• Genuine curiosity about generative AI as a tool for improving how your team builds, ships, and improves over time.

Responsibilities

• Define and evolve the team's domain: offer reconciliation, post-claim consumer experiences, receiptful/receiptless transaction flows, and self-heal capabilities ; adapting as Upside's needs grow.
• Champion quality across the reconciliation stack: accuracy, reliability, observability, scalability, and clear decision-making in the systems that determine cash-back outcomes.
• Keep the platform secure, resilient, and production-ready, with the tooling and practices that make iteration safe and diagnosis fast.
• Act as a player-coach, contributing hands-on in high-leverage areas while guiding execution and modeling smart use of AI to speed up development, debugging, and system understanding.
• Be the team's main cross-functional partner with Product, Design, Data, Consumer Ops, and partners, keeping roadmap and strategy tied to real gains in transaction success and user trust.

Skills

Engineering Leadership

Team scaling

Mobile API infra

AWS

REST

Microservices

Kotlin Multiplatform

Python/Java back-end

AI/GenAI

Cross-functional collaboration

Tools

Snowflake

Hex

AWS

Job description

Upside is seeking an Engineering Manager to lead the Reconciliation team, a full-stack group responsible for the transaction-matching pipeline spanning Kotlin Multiplatform front-end and Python/Java back-end.

You will drive quality, scale systems, and coach engineers while partnering with Product, Data, and Operations to improve cash-back accuracy and user trust. This role blends hands-on leadership with strategic direction in a hybrid, multi-city setting.