Skip to content
UpsideUpsideWashington, DC

Engineering Manager, Reconciliation

Leads the Reconciliation engineering team responsible for transaction matching, cashback accuracy, and post-claim experiences across mobile and backend systems. The role combines people leadership, hands-on technical contribution, operational excellence, and cross-functional product strategy.

188k – 220k/yr
Hybrid5+ YOEEngineering Management

About the role

Responsibilities

  • Lead the Reconciliation team, a full-stack group responsible for Upside’s transaction-matching pipeline across Kotlin Multiplatform front-end and Python and Java back-end systems.
  • Build a safe, collaborative team and foster open discussion.
  • Improve quality, performance, speed, and engineering standards.
  • Coach engineers, recognize achievements, and support professional growth.
  • Define and evolve the team’s domain, including offer reconciliation, post-claim consumer experiences, receiptful and receiptless transaction flows, and self-healing capabilities.
  • Champion accuracy, reliability, observability, scalability, and clear decision-making across the reconciliation stack.
  • Keep the platform secure, resilient, and production-ready.
  • Contribute hands-on in high-leverage areas while guiding execution and modeling effective use of generative AI.
  • Partner with Product, Design, Data, Consumer Operations, and external partners on roadmap and strategy.

Requirements

  • 3+ years of engineering management experience.
  • Track record of scaling teams and improving systems amid ambiguity.
  • Technical depth across mobile and API infrastructure and back-end data tools.
  • Familiarity with mobile and API development patterns, including serverless, event-driven systems, REST, microservices, MVI, and Clean Architecture.
  • Curiosity about generative AI as a tool for improving software development and operations.

Nice-to-haves

  • Experience with mobile or distributed API domains.
  • Experience with AWS.
  • Experience with Snowflake, Hex, or similar back-end data tools.

Compensation and Benefits

  • Equity through incentive stock options.
  • Medical, dental, and vision coverage beginning on the first day.
  • 401(k) program.
  • Family planning programs and paid parental leave.
  • Fitness and wellness memberships.
  • Emotional and mental health support programs.
  • Unlimited paid time off, 10 paid federal holidays, and an annual week-long winter break.
  • Flexible work environment.
  • Lunch reimbursement for in-office employees.
  • Employee Resource Groups.
  • Learning and Development stipend.

Skills

kotlin multiplatformKotlinPythonJavaAWSSnowflakeHexrestMicroservicesserverlessEvent-Driven Architecturemviclean architectureGenerative AI

Similar roles

Engineering Management jobs
Datadog

Manager I, Engineering

DatadogNew York, NY

Engineering Manager leading the Onboarding Growth team at Datadog. Responsible for setting product direction, coaching engineers, building UX features, data platforms, and AI-assisted onboarding experiences to help new users quickly realize value from the platform. Requires 2+ years people management and full stack team experience.

187k – 240k/yrHybrid5+ YOEEngineering Management
Datadog

Manager I, Engineering - Change Experience Platform

DatadogNew York, NY

Hands-on engineering manager to lead a team building internal UI/CLI frameworks, change-management workflows, notifications, and infrastructure governance tools for Datadog engineers. Requires backend experience, platform/tooling background, and people-management skills.

187k – 240k/yrHybrid5+ YOEEngineering Management
Datadog

Manager I, Engineering - Core Analytics

DatadogNew York, NY

Leads small team of data engineers building scalable Core Analytics Data Access Platform. Owns technical direction, codes hands-on, ensures security/governance, and partners with AI/analytics teams. Requires data engineering and AWS/Spark experience.

187k – 240k/yrHybridEngineering Management
Datadog

Manager I, Engineering - Applied AI - Natural Language & Conversational Interfaces

DatadogNew York, NY

Lead engineering teams building natural language interfaces and conversational AI systems using LLMs, RAG, and agentic architectures. Requires technical expertise in AI/ML/NLP, people management, and experience shipping LLM-powered products.

187k – 240k/yrHybridEngineering Management
Databricks

Engineering Manager, Foundation Model Inference

DatabricksMountain View, CA

Lead and grow a team of infrastructure engineers building Databricks' Foundation Model Inference and APIs for serving partner and self-hosted LLMs at scale. Shape roadmaps for real-time, provisioned, and batch inference while maintaining high reliability, operational excellence, and technical quality.

190k – 261k/yrOn-site5+ YOEEngineering Management