About Polymarket Polymarket is the world’s largest prediction market platform. We enable individuals to express views on real-world events by trading on outcomes across politics, economics, sports, culture, and current affairs. Built as a peer-to-peer marketplace with no centralized “house,” Polymarket aggregates diverse opinions into transparent, market-based probabilities that reflect collective expectations about the future. We're growing fast – both in terms of volume ($21B traded in 2025) and adoption as an alternative news source. Our ambition is to become a ubiquitous beacon of truth in global media and we need your help adding fuel to the fire. About the Role Polymarket is looking for a world-class infrastructure engineer to join our team and help scale the systems that power our products. You’ll be responsible for designing, building, and maintaining the backbone of our engineering platform—from developer workflows and CI/CD pipelines to core infrastructure that supports high-performance APIs and data services. You’ll have the autonomy to make big technical decisions, drive system architecture, and implement solutions that balance speed, reliability, and long-term maintainability. What You’ll Do We're looking for an experienced individual contributor who enjoys optimizing mission-critical infrastructure. Build & automate development workflows. You’ll design and maintain infrastructure that standardizes how we develop, version, test, and deploy software across environments. Architect scalable systems. You’ll make thoughtful architectural decisions and tradeoffs, balancing risk, performance, cost, and maintainability. Power high-performance services. You’ll contribute to infrastructure supporting real-time APIs and low-latency data feeds. Develop testing infrastructure. You’ll build robust tooling for automated testing at all levels—from unit to integration to API. Ensure availability & reliability. You’ll own critical infrastructure that minimizes downtime and reduces risk of failure. Move fast without breaking things. You’ll deliver high-quality solutions quickly, with a strong sense of ownership and attention to detail. Operate autonomously. You’ll take initiative and make independent decisions—no micromanagement here. Collaborate across teams. You’ll work closely with engineers throughout the company to support deployment, performance, and operational needs. What We’re Looking For 6+ years of hands-on experience in software engineering, with a strong track record of delivering production-grade systems. Deep familiarity with cloud infrastructure and DevOps tooling, including AWS, Kubernetes (K8s), Terraform, Kafka, load balancing, ElasticCache, messaging queues, Flux, Docker, GitHub Workflows, Cloudflare, FluxCD, PostgreSQL, MongoDB, Redis, S3, Lambda, and AWS networking (VPCs, VPC Peering). Excellent communication skills and a strong desire to learn, grow, and collaborate effectively across teams. Solid technical acumen and a results-driven mindset, capable of solving complex engineering challenges with practical solutions. Proven history of improving engineering workflows, through the creation and implementation of new tools and processes that boost efficiency and consistency. Leadership experience in planning and executing large-scale projects, with lasting impact on core systems or engineering teams. Ability to ship quickly and iterate fast, without compromising quality. Exceptional judgment in prioritizing tasks, balancing urgency with strategic importance. Growth-oriented mindset, with a steep learning curve and an eagerness to evolve with the role. Genuine passion for engineering—you take pride in your craft and strive for excellence in everything you build. Specialized expertise in at least one of the following areas: Networking: demonstrated ability to diagnose and resolve complex network-related issues. Security: Relevant certifications, such as CISSP, CISM, or AWS certifications, or equivalent experience in designing secure systems. (PLUS) Proven experience building deployment systems in: K8S RDS / PSQL IAM policies/roles ElasticCache Cloud Networking (VPC peering, subnets, etc) Benefits Competitive salary & equity Unlimited PTO, Health, Vision, & Dental coverage 401k match Hardware setup — new MacBook Pro, big display, & accessories.

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 Compensation: The US base salary range for this full-time position is $150,000 - $180,000 + 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 accommodations@upside.com. 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.

• Lead the design and architecture of scalable, resilient, and secure cloud-native platforms and infrastructure on cloud platforms like AWS and GCP. • Develop, manage, and champion the use of IaC tools like Terraform and Crossplane to automate infrastructure provisioning and management. • Build, maintain, and optimize CI/CD pipelines using GitHub Actions and ArgoCD to automate the build, testing, and deployment of applications, enabling faster and more reliable software delivery. • Manage and scale our containerized environments using technologies like Docker and Kubernetes. • Implement and manage robust monitoring, logging, and alerting solutions (e.g., Prometheus, Grafana, Datadog) to ensure system health and proactively identify and resolve issues. • Identify problems, develop and implement solutions, and drive innovation to improve infrastructure performance, stability, and efficiency. • Work closely with development teams to provide self-service tools and platforms, troubleshoot complex issues, and act as a subject matter expert for our infrastructure. • Implement and enforce security best practices, conduct security assessments, and ensure compliance with industry standards. • Provide technical guidance and mentorship to junior engineers, fostering a culture of technical excellence and continuous improvement.

• Design and maintain organization’s on-premises and Azure infrastructure. • Ensure the stability, security, and scalability of mission-critical systems. • Architect, deploy, and optimize Azure Virtual Machines. • Lead identity and access design using Azure AD, RBAC, and conditional access controls. • Oversee Azure governance including policies and cost optimization. • Drive modernization efforts including virtualization improvements and Azure migration. • Lead major infrastructure projects and cloud transformations end-to-end. • Mentor junior engineers and drive knowledge sharing.