Senior Infrastructure Engineer

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.

We're looking for an Infrastructure Engineer to join the Platform Infrastructure team s 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 Dev Ops, 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 Git Hub.
• Provide guidance to more junior team members when applicable, and proactively seek feedback and mentorship to support your growth.

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.

• Have 3+ years of experience in an infrastructure, Dev Ops, 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 Git Hub 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…