Engineering Manager - Reconciliation & Cash-Back Platform

Upside; Washington (District of Columbia); Hybrid; USD 188,000 - 215,000; Full time

Benefits offered by this job

Medical coverage

Dental & Vision

Equity (ISOs)

401(k) plan

Paid parental leave

Unlimited PTO

Flexible work environment

Learning stipend

Job summary

Upside in Washington, DC area is seeking an Engineering Manager for the Reconciliation team to lead a full-stack group spanning Kotlin Multiplatform front-end and Python/Java back-end. This role owns the post-claim experience, verifying transactions and awarding cashback.

You will blend technical depth with people-first leadership, drive operational excellence, grow your team, and align with Product, Design, Data, and Partnerships to scale the core platform.

Qualifications

• 3+ years of engineering management experience.
• Experience scaling teams and improving systems.
• Deep technical focus on mobile and API infra (AWS a plus).
• Interest in applying generative AI to improve development.

Responsibilities

• Define and evolve the team's domain: reconciliation, post-claim experiences, transaction flows.
• Champion quality across the reconciliation stack: accuracy, observability, scalability.
• Keep the platform secure, resilient, and production-ready with safe tooling.
• Act as player-coach, hands-on in high-leverage areas and leverage AI to speed up work.
• Partner with Product, Design, Data, Consumer Ops, and partners on roadmap execution.

Skills

Engineering leadership

Scaling teams

Mobile & API infra

AI in development

Tools

AWS

Snowflake

Hex

REST API

Job description

Upside in Washington, DC area is seeking an Engineering Manager for the Reconciliation team to lead a full-stack group spanning Kotlin Multiplatform front-end and Python/Java back-end. This role owns the post-claim experience, verifying transactions and awarding cashback.

You will blend technical depth with people-first leadership, drive operational excellence, grow your team, and align with Product, Design, Data, and Partnerships to scale the core platform.