Upside · 5 hours ago
Senior Infrastructure Engineer I
Chicago, IL
Full-time
Hybrid
Mid, Senior Level
$150K/yr - $180K/yr
3+ years expUpside is transforming brick-and-mortar commerce with technology that enhances value for users and businesses alike. The Infrastructure Engineer will work with the Platform Infrastructure team to build and support systems that enhance software development, deployment, and operations, focusing on improving reliability and security.
AppsBusiness DevelopmentData ManagementMarketplaceMobile AppsRetailRetail Technology
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
Qualification
Required
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
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!
Company
Upside
Upside is a two-sided marketplace focused on driving value to all points of brick and mortar commerce.
201-500 employees
H1B Sponsorship
Upside has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2025 (1)
2024 (1)
2023 (1)
2022 (1)
Funding
Current Stage
Late StageTotal Funding
$165MKey Investors
General Catalyst
2022-04-26Series D· $65M
2022-04-26Debt Financing· $100M
2020-08-31Series C
Leadership Team
Alex Kinnier
Co-founder & CEO
Jan Rubio
Co-founder
Recent News
2025-07-02
Progressive Grocer
2025-02-18
Company data provided by crunchbase