Senior Infrastructure Engineer II

Job Overview

Upside is transforming brick-and-mortar commerce with technology that brings the sophistication of online retail to physical stores. Our platform helps millions of users earn more cashback and businesses gain profitable customers. Billions of dollars in commerce run through our platform annually, benefiting consumers, retailers, and sustainability initiatives.

About the Role

We're seeking an Infrastructure Engineer to join the Platform Infrastructure team. This team builds and supports 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 platform reliability, efficiency, and security. You’ll contribute to core tooling, learn best practices for scaling infrastructure, and have a meaningful impact on product delivery and developer experience.

Key Responsibilities

• Contribute to infrastructure initiatives that improve platform reliability, security, and developer experience


• Collaborate with teammates and product engineers to identify pain points in build, test, or deploy workflows


• Implement infrastructure-as-code modules using Terraform to maintain and extend AWS resources


• Participate in the team’s shield rotation, helping investigate issues, respond to incidents, and ensure system resilience


• Document your work clearly and contribute to team best practices


• Provide guidance to junior team members and proactively seek feedback

Ideal Qualifications

• 6+ years of experience in infrastructure, DevOps, platform, or SRE roles


• Familiarity with AWS, Terraform, and GitHub (or equivalent tooling)


• Proficiency in at least one scripting or programming language (Python, Bash, or Go)


• Experience with CI/CD systems like GitHub Actions or Jenkins


• Understanding of monitoring, alerting, and observability


• Strong communication and collaboration skills

Benefits

Medical, dental, and vision coverage
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 + annual Winter Break
Flexible work environment
Lunch reimbursement for in-office employees
Employee Resource Groups
Learning and Development stipend
Transparent culture