Engineering Manager, Reconciliation

Meet Upside:

We created Upside to transform brick-and-mortar commerce. Our technology uses the sophistication of online retailprofit measurement attribution and incrementalityto provide users with more value on their everyday purchases and brick-and-mortar businesses with new profitable customers. Weve 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 thats delightful to use.

Were looking for an Engineering Manager to lead our Reconciliation team: a full-stack group responsible for Upsides 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 its due and help users recover when something goes wrong.

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

How youll make an impact

• Build a safe collaborative team. Name problems openly and invite discussion its 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 youll own

• Define and evolve the teams domain: offer reconciliation post-claim consumer experiences receiptful/receiptless transaction flows and self-heal capabilities ; adapting as Upsides 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 teams 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 were 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; were 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 attendance is required on Monday Tuesday and Thursday and may increase based on project-based needs and changes to Upsides in-office policy over time.

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

• Tier 1: NYC $207000 - $237000

• Tier 2: Austin Chicago Washington DC $188000 - $215000

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.

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. Were 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 theres anything we can do to support a disability or special need during your application or interview process please email

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.

Required Experience:

Manager