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.
#LI-HYBRID
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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 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 accommodations@upside.com.
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.
