Engineering Manager, Reconciliation

About the role

At Upside, engineering leaders help teams make the right calls quickly; gathering the right input, taking smart risks, and shipping high-quality software that's delightful to use. We are looking for an Engineering Manager to lead our Reconciliation

team: a full-stack group responsible for Upside's transaction-matching pipeline, spanning our Kotlin Multiplatform (KMP) front-end and our Python + Java back-end. This team owns the post-claim experience; making sure Upside can accurately verify a transaction, award cash back when it's due, and help users recover when something goes wrong. You will combine technical depth with people-first leadership to drive operational excellence, grow your team, and scale the systems behind our core product. You will also partner closely with other engineering leaders on organizational and technical strategy across our Consumer and Partnerships platforms.

What you'll do

• Build a safe, collaborative team where problems are named openly and discussion is invited, because this is how your team does its best work.
• Lean in beyond your lane with a first-team mindset, jumping in wherever the organization needs help and supporting peers through critical workflows.
• Raise the bar consistently by spotting and driving improvements in quality, performance, speed, and engineering standards across the reconciliation lifecycle.
• Grow your people through deliberate coaching, recognizing wins, and helping engineers build skills that serve them for years in technology.
• Create clarity, not control, by setting clear expectations so your team can operate with independence, confidence, and focus.
• Partner as a strategic bridge with Product, Design, Data, Consumer Ops, and external partners to align on shared objectives.
• Champion the use of generative AI as a practical tool to speed up development, debugging, and system understanding for your team.

What you'll own

• Define and evolve the team's domain in offer reconciliation, post-claim consumer experiences, receiptful and receiptless transaction flows, and self-heal capabilities, adapting as Upside's needs grow.
• Champion quality across the reconciliation stack by owning accuracy, reliability, observability, scalability, and clear decision-making in the systems that determine cash-back outcomes.
• Keep the platform secure, resilient, and production-ready by maintaining 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 main cross-functional partner for the Reconciliation team with Product, Design, Data, Consumer Ops, and partners, keeping roadmap and strategy tightly tied to real gains in transaction success and user trust.

Requirements

• 3+ years of engineering management experience, with mobile or distributed API domains being a strong plus, but we care most about your leadership track record in delivering results.
• A track record of scaling teams and leveling up systems, even when the path forward is unclear and ambiguity is high.
• Comfort going deep on technical challenges across mobile and API infrastructure, with AWS experience being a strong advantage, and back-end data tools such as Snowflake, Hex, and similar platforms.
• Hands-on familiarity with mobile and API development patterns, including serverless, event-driven architectures, REST, microservices, MVI, and Clean Architecture, is a plus; we are happy to help you build on what you already know.
• A bias toward clarity over consensus, especially when things are moving fast and decisions need to be made with incomplete information.
• Genuine curiosity about generative AI and a thoughtful approach to how it can improve how your team builds, ships, and iterates on products over time.
• A commitment to building inclusive, collaborative teams where different perspectives are welcomed and psychological safety is maintained.
• The ability to communicate effectively with both technical and non-technical stakeholders, translating complex topics into clear, actionable plans.

Engineering Culture

We want our engineering leaders to have the time to coach and enable growth for their engineers, as well as the space to make thoughtful and impactful technical contributions. We ask our managers to focus on a team of around 6-8 direct reports, while our more senior managers may operate across two teams. The staffing for these reports is always split; we see incredible value from a mix of full-time and contract staff.

Location

This hybrid role is based in our Austin, Chicago, DC, or NYC office. In-office attendance is required on Monday, Tuesday, and Thursday and may increase based on project-based needs and changes to Upside's in-office policy over time.

• Tier 1: NYC $207,000 - $237,000
• Tier 2: Austin, Chicago, Washington, DC $188,000 - $215,000

In addition to base salary, this position is also eligible for equity and comprehensive benefits. The final starting pay will be determined based on job-related skills, experience, qualifications, work style, and demonstrated impact.