Engineering Manager, Reconciliation Platform

Upside; Washington; Hybrid; USD 188,000 - 237,000; Full time

Benefits offered by this job

Medical coverage

Equity

401(k)

Parental leave

Wellness memberships

Mental health support

Unlimited PTO

Flexible work

Lunch reimbursement

ERGs

Learning stipend

Transparent culture

Amazing mission

Job summary

Upside is seeking an Engineering Manager to lead the Reconciliation team — a full‑stack group spanning Kotlin Multiplatform front end and Python/Java back end. You’ll shape post‑claim experiences, ensure accurate cash‑back, and scale the systems that power our core product.

You’ll coach engineers, partner with Product, Design, Data, and Ops, and drive operational excellence. This hybrid role is based in Austin, Chicago, DC, or NYC with in‑office days as needed, and comes with equity and

Qualifications

• 3+ years of engineering management experience.
• Track record of scaling teams and leveling up systems.
• Hands-on familiarity with mobile and API development patterns: serverless, event-driven, REST, microservices.
• A bias toward clarity over consensus, especially when things move 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: reconciliation, post-claim experiences, receiptful/receiptless flows, and self-heal capabilities.
• Champion quality across the reconciliation stack: accuracy, reliability, observability, scalability, and clear decision-making.
• Keep the platform secure, resilient, and production-ready with tooling and practices for safe iteration.
• Act as a player-coach, contributing hands-on in high-leverage areas while guiding execution and AI usage to speed up development.
• Be the team’s cross-functional partner with Product, Design, Data, Consumer Ops, and partners.

Skills

Engineering leadership

Team scaling

AWS

Serverless

REST APIs

Microservices

Clean Architecture

Generative AI

API infrastructure

Tools

Snowflake

Hex

KMP

Python

Java

Job description

Upside is seeking an Engineering Manager to lead the Reconciliation team — a full‑stack group spanning Kotlin Multiplatform front end and Python/Java back end. You’ll shape post‑claim experiences, ensure accurate cash‑back, and scale the systems that power our core product.

You’ll coach engineers, partner with Product, Design, Data, and Ops, and drive operational excellence. This hybrid role is based in Austin, Chicago, DC, or NYC with in‑office days as needed, and comes with equity and