Senior Engineering Manager

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 a Senior Engineering Manager to lead the Infrastructure and Data Platform teams, two foundational groups responsible for Upside’s core platforms. These teams provide the cloud, data, and analytics capabilities that power every application, insight, and decision across the company. This leader will combine technical competence with people-first leadership to drive operational excellence, foster growth, and scale the systems that underpin our product and internal platforms.

This role will also help close a strategic gap in our technical organization by guiding the evolution of MLOps practices that support data science and machine learning innovation.

Here are some ways we have seen leaders drive impact at Upside:

• 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:

• Champion system-level quality by identifying and addressing gaps in reliability, scalability, security, and performance across infrastructure and analytics systems.

• Ensure the cloud platform is secure, cost-efficient, and production-ready, and that the data stack enables self-service, repeatable, and trusted workflows.

• Shape technical direction across DevOps, DataOps, and MLOps domains, and drive strategic upgrades such as orchestrator migrations, cloud modernization, and analytics workflow enablement.

• Oversee large-scale programs that span infrastructure, data, and analytics domains, aligning execution with business priorities and cross-team dependencies.

• Establish and monitor key operational metrics (e.g., platform availability, cost per transaction, data pipeline reliability, MLOps readiness).

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

• Represent the infrastructure and analytics engineering teams in cross-functional planning, technical councils, and long-term roadmap discussions.
  
  

You May Be a Fit If You:

• Have 5+ years of engineering management experience, ideally across platform, data, or infrastructure domains.

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

• Have familiarity with cloud infrastructure (AWS preferred), modern data platforms (e.g., Snowflake, dbt), and orchestration tools (e.g., Dagster, Airflow).

• Have hands-on experience or deep familiarity with MLOps practices, such as model versioning, deployment, monitoring, and reproducibility.

• 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 $210,000 - $260,000+ 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!

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

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.