IT Engineering Manager

Newmark; Chicago (IL); Hybrid; USD 188,000 - 215,000; Full time

Benefits offered by this job

Equity (ISOs)

401(k) program

Family planning programs

Paid parental leave

Wellness memberships

Unlimited PTO + holidays

Lunch reimbursement

Learning & Development stipend

Diversity & inclusion

Job summary

Upside is seeking an Engineering Manager to lead the Reconciliation team, overseeing a full-stack stack (KMP front-end, Python/Java back-end) and driving quality, scalability, and growth. You’ll coach engineers, set domain strategy, and partner with Product, Design, Data, and Ops to improve transaction success and user trust.

Expect a hands-on leadership role with a bias for clarity, serving a team of 6–8 direct reports across hybrid locations (Austin, Chicago, DC, NYC) and a base salary

Qualifications

• 3+ years of engineering management experience.
• Track record of scaling teams and systems.
• Deep technical focus across mobile and API infra (AWS a plus).
• Hands-on with mobile and API development patterns (serverless, REST, microservices).
• Bias toward clarity and outcomes; curiosity about generative AI.

Responsibilities

• Define and evolve the team’s domain: reconciliation, post-claim experiences, and self-heal flows.
• Champion quality across the stack: accuracy, observability, scalability, and reliable cash-back outcomes.
• Keep platform secure, resilient, and production-ready with safe tooling and fast diagnosis.
• Act as player-coach, contributing hands-on in high-leverage areas while guiding execution.
• Partner with Product, Design, Data, Consumer Ops, and partners to align roadmaps with business gains.

Skills

Leadership

Engineering management

Scalable systems

AWS

REST / APIs

Microservices

AI in development

Tools

AWS

Snowflake

Hex

Job description

Engineering Manager - Reconciliation Team

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.

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.

• 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 employees
• Employee 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.