Senior Infrastructure Engineer I

Job Overview

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

We're looking for an Infrastructure Engineer to join the Platform Infrastructure team at Upside. This team builds and supports the systems that power how engineering teams develop, deploy, and operate software—from cloud infrastructure to CI/CD, observability, and security automation. In this role, you’ll work closely with product and security engineers to deliver infrastructure features that improve the reliability, efficiency, and security of our platform.

You’ll contribute to core tooling, learn best practices for scaling infrastructure in a growing company, and have a meaningful impact on product delivery and developer experience. This is a great opportunity for someone with a solid foundation in infrastructure or DevOps, who is looking to deepen their impact and grow their technical breadth in a high-ownership environment.

Key Responsibilities

• Contribute to infrastructure initiatives that improve platform reliability, security, and developer experience, such as CI/CD pipeline improvements, cost optimization, and automation of manual workflows.


• Collaborate with teammates and product engineers to identify pain points in build, test, or deploy workflows and deliver well-scoped improvements using existing platform tools and patterns and developing new ones where needed.


• Implement infrastructure-as-code modules using Terraform, helping maintain and extend AWS resources in a reliable and consistent way.


• Participate in the team’s shield rotation, helping investigate org-wide issues, respond to incidents, and ensure our systems are resilient and well-monitored.


• Document your work clearly, contribute to team best practices, and help others adopt infrastructure patterns by sharing knowledge in Slack, Confluence, and GitHub.


• Provide guidance to more junior team members when applicable, and proactively seek feedback and mentorship to support your growth.

Ideal Qualifications

• Have 3+ years of experience in an infrastructure, DevOps, platform, or SRE role supporting production systems.


• Are familiar with AWS, Terraform, and GitHub (or equivalent infrastructure tooling), and excited to deepen your knowledge in these areas.


• Are proficient in at least one scripting or programming language, such as Python, Bash, or Go.


• Have experience working with CI/CD systems like GitHub Actions, Jenkins, or similar tools.


• Understand the value of monitoring, alerting, and observability and have contributed to system reliability efforts.


• Take initiative to understand the systems you work on, ask thoughtful questions, and raise blockers early.


• Communicate clearly and work collaboratively within a team environment, contributing to planning and retrospectives.

Engineering Culture

We want our engineers to have the time and support to grow in their craft and contribute meaningfully to impactful technical decisions. Engineers are encouraged to focus deeply on their work, collaborate effectively with team members, and continuously develop their skills. Teams are thoughtfully staffed to create a dynamic and diverse environment that enhances learning and innovation.

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.

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!