Engineering Manager, Reconciliation

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

Meet Upside

We created Upside to transform brick-and-mortar commerce. Our technology uses the sophistication of online retail—profit measurement, attribution, and incrementality to provide users with more value on their everyday purchases and brick-and-mortar businesses with new, profitable customers. We’ve helped millions of users earn 2 to 3 times more cashback than any other product, and hundreds of thousands of brick-and-mortar businesses earn measurable profit. Billions of dollars in commerce run through the Upside platform every year, and that value goes directly back to our retailer partners, the consumers they serve, and important sustainability initiatives.

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're 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'll combine technical depth with people-first leadership to drive operational excellence, grow your team, and scale the systems behind our core product. You'll also partner closely with other engineering leaders on organizational and technical strategy across our Consumer and Partnerships platforms.

How You'll Make An Impact

• Build a safe, collaborative team. Name problems openly and invite discussion, it's how your team does its best work.
• Lean in beyond your lane. Bring a first-team mindset, jumping in wherever the org needs help.
• Raise the bar. Spot and drive improvements in quality, performance, speed, and engineering standards.
• Grow your people. Coach engineers, recognize their wins, and help them build skills that serve them for years.
• Create clarity, not control. Set clear expectations so your team can operate with independence and confidence.

What You'll Own

• 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.

What We're Looking For

• 3+ years of engineering management experience, mobile or distributed API domains are a strong plus, but we care most about your leadership track record.
• A 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.

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.

Compensation

The U.S. base salary range for this full-time position varies by work location:

• 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 benefits.

The final starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. Your recruiter can share more about the specific salary range for your location during the hiring process.

Compensation Range: $188K - $220K

Benefits

• Medical, dental, and vision coverage starting on Day 1
• Equity (ISOs)
• 401(k) program
• Family planning programs + paid parental leave
• Physical fitness and wellness memberships
• Emotional and mental health support programs
• Unlimited PTO + 10 paid federal holidays + our annual, week-long Winter Break
• Flexible work environment
• Lunch reimbursement for in-office employeesEmployee Resource Groups
• Learning and Development stipend
• Transparent culture
• Amazing mission!

Diversity And Inclusion

Diversity drives innovation, and our differences make us stronger. We‘re passionate about building a workplace that represents a variety of backgrounds, skills, and perspectives, and we do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. Everyone is welcome here!

If there's anything we can do to support a disability or special need during your application or interview process, please email [e-mail].

This email is for accessibility accommodations only, it should not be used to submit job applications.

Notice To Recruiters And Placement Agencies

This is an in-house search with a dedicated recruiter. Please do not submit resumes to any person or email address at Upside. Upside is not liable for, and will not pay, placement fees for candidates submitted by any party or agency other than its approved recruitment partners.