Senior Infrastructure Engineer II

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.

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

• 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.

Why You Should Apply

This role is a good fit for you if:

• You aren’t afraid to challenge the status quo when it makes the team and business better. You learn from those around you while utilizing data to advocate for informed change.

• You thrive at the intersection of systems and storytelling, not only building robust solutions but also communicating their purpose, impact and rationale, so teams can experiment, iterate, and act confidently.

• You care about building resilient systems that scale. You bring a mindset of continuous improvement, and know when to invest in observability, automation, or new infrastructure to reduce toil and improve outcomes for the team and end users.

• You believe that pulling quality upstream starts with engineering. You champion best practices, encourage early testing and validation, and work closely with peers to build a culture of quality from the ground up.

Ideal Qualifications

• Have 6+ 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.

Compensation:

The US base salary range for this full-time position is $170,000 - $210,000 + 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.

#LI-Hybrid

#LI-NE1

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].

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.