PRINCIPAL, TECHNOLOGY ENGINEERING

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:
As engineering leaders at Upside, we strive to gather the right information from those around us and take the right calculated risks. In doing so, we hope to help teams quickly make key decisions that will ship high quality software with the most delightful experience possible to our users.

We’re looking for an Engineering Manager to lead the Consumer Core team, a full‑stack group responsible for Upside’s core functionality within our Kotlin Multiplatform (KMP) front‑end and our Python + Java driven back‑end. This team delivers the architectural foundations and security patterns that empower our Consumer full‑stack teams to build scalable features across the entire funnel. This leader will combine technical competence with people‑first leadership to drive operational excellence, foster growth, and scale the systems that underpin our primary product platform.

This role will also work closely with other engineering leaders to plan and guide organizational and technical strategy to support both our Consumer and Partnerships applications and systems.

Impact of our leaders:

Create a safe, collaborative team environment. You name problems and invite open discussion, which motivates your team to do their best work.

Operate with a first‑team mindset. You lean in when important areas need help, regardless of whether it's “your” domain, and prioritize the success of the whole organization.

Raise the bar. You identify and influence improvements in quality, performance, speed of execution, and engineering standards.

Grow talent. You coach your engineers, recognize their achievements, and help them develop skills that will benefit them and Upside for years to come.

Set clarity and empower autonomy. You ensure expectations and direction are clearly articulated so that individuals and teams can operate with independence, confidence, and creativity.

In addition to the leadership responsibilities above, you will:

Clearly define and maintain the team’s domain boundaries across authentication, event architecture, user research and analytical workflows, internal mobile tooling, app security support, mobile FinOps, and cross‑team repos, while leaving room for evolution as Upside’s needs change.

Champion system‑level quality by identifying and addressing gaps in reliability, scalability, security, and performance across our app and API stack.

Ensure the consumer app platform is secure, cost‑efficient, and production‑ready, and that the development stacks and tooling enable self‑service, repeatable, and trusted workflows.

Oversee team AI adoption and general exploration strategy to keep our KMP, Python, and Java platforms on the frontier of industry‑leading tools and integrations.

Act as the primary point of contact for internal partners (e.g. Product, Design, Security, and Data Science), ensuring platform capabilities support evolving business needs.

Represent the Consumer Core team in cross‑functional planning, technical councils, and long‑term roadmap discussions.

You May Be a Fit If You:

Have 3+ years of engineering management experience, ideally across mobile or distributed API domains.

Thrive in environments where you’re asked to scale teams, elevate systems, and solve ambiguity in equal measure.

Have familiarity with mobile and API infrastructure (AWS preferred), analytical and SDLC tools (e.g., Mixpanel, Runway).

Have hands‑on experience or familiarity with mobile and API development best practices, including serverless, event‑driven, REST, microservices, MVI, and Clean architecture patterns.

Value clarity over consensus and help teams stay aligned through high‑change, high‑growth conditions.

Are interested in integrating generative AI into team workflows and engineering processes to improve delivery speed, quality, and developer productivity, and foster continuous improvement across the development lifecycle.

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 decisions. We ask our managers to focus on a team of around 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 US base salary range for this full‑time position is $185,000 - $225,000 + equity + 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 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. 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!

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