Observability/CI/CD Cloud Engineering Manager

Groupon is a marketplace where customers discover new experiences and services everyday and local businesses thrive. To date we have worked with over a million merchant partners worldwide, connecting over 16 million customers with deals across various categories. In a world often dominated by e-commerce giants, we stand out as one of the few platforms uniquely committed to helping local businesses succeed on a performance basis. Groupon is on a radical journey to transform our business with relentless pursuit of results. Even with thousands of employees spread across multiple continents, we still maintain a culture that inspires innovation, rewards risk-taking and celebrates success. The impact here can be immediate due to our scale and the speed of our transformation. We're a "best of both worlds" kind of company. We're big enough to have the resources and scale, but small enough that a single person has a surprising amount of autonomy and can make a meaningful impact. Lead the AI-Driven Evolution of Groupon's Global Engineering Platform At Groupon, we're rebuilding our platform from the ground up—and AI is at the core of this transformation. We're looking for a hands-on, strategic Engineering Manager to own our Observability and CI/CD disciplines, driving the next phase of our digital evolution. This is an opportunity to champion AI-first engineering practices and modernize mission-critical infrastructure for 300+ engineers worldwide. What You'll Do Lead & Inspire: Build and mentor a high-performing, globally distributed team of CI/CD and Observability engineers (5-10 direct reports), coaching them in cutting-edge AI-assisted workflows and best practices. Modernize Core Infrastructure: Spearhead the migration from legacy platforms (Jenkins, ELK) to cloud-native solutions (GitHub Actions, Google Cloud Logging, GCP Prometheus/Grafana). Eliminate "straggler" pipelines and drive cost-efficient, reliable operations. AI-First Engineering: Operationalize AI tools (Claude Code, Copilot, ChatGPT, etc.) for everything from log analysis and incident summaries to automated infrastructure as code, making AI-augmented engineering a daily norm. Architect & Optimize: Oversee a hybrid tech stack (Kubernetes, Envoy, Terraform, GCP, AWS), ensuring platforms are fast, scalable, and "self-healing" via LLM integrations. Collaborate Globally: Act as a thought leader and cross-functional partner, advocating for AI-driven developer experience and collaborating with leaders in SRE, Product, and Cloud. Drive Transformation: Deliver strategic projects with tight deadlines and direct business impact, such as the Jenkins-to-GHA and ELK-to-GCP migrations, while maintaining a high standard of technical excellence and cost efficiency. The Stack & Tools: Cloud Platforms: Google Cloud Platform (GCP), AWS CI/CD: Jenkins, GitHub Actions Observability: ELK (Elastic, Logstash, Kibana), Prometheus, Grafana, GCP Native Logging, Thanos Infrastructure: Kubernetes, Docker, Terraform, Ansible Programming/Scripting: (Nice to have) Java, Golang, Typescript/Node (for pipeline/tooling), Bash Generative AI/Automation: Claude Code, GitHub Copilot, LLMs for log analysis & code generation What We're Looking For 5+ years' experience leading infrastructure, DevOps, or SRE teams (5+ people), ideally in high-change, scale-up environments. Deep technical expertise in cloud-native platforms, observability, infrastructure as code, and CI/CD tooling. Proven success operationalizing AI tools within engineering workflows (not just the AI "hype"—real-world impact). Strategic, resilient, and pragmatic approach: ready to own results and thrive under shifting priorities. Exceptional communication: able to simplify complexity and effectively partner with C-level and global teams. Bachelor's or Master's in Computer Science (or similar)—or equivalent industry experience. Bonus Points For GCP migration project delivery (AWS-to-GCP consolidation, etc.) Track record automating log analysis or incident management using AI Experience managing global, hybrid teams and large-scale distributed cloud workloads Why Groupon? Drive real, high-visibility change at the heart of a company undergoing major transformation. Work on complex technical and operational challenges in a fast-paced, AI-first environment. Accelerate your impact—and your team's—using industry-leading AI and automation tools. Influence engineering practices across a global platform impacting millions of users. Ready to be part of Groupon's new chapter? If you thrive in dynamic environments, care deeply about both technology and people, and are passionate about harnessing AI to drive transformation, we want to meet you. Bring your expertise, your leadership, and your ideas—you'll shape the future with us. Groupon is an AI-First CompanyWe're committed to building smarter, faster, and more innovative ways of working—and AI plays a key role in how we get there. We encourage candidates to leverage AI tools during the hiring process where it adds value, and we're always keen to hear how technology improves the way you work. If you're passionate about AI or curious to explore how it can elevate your role—you'll be right at home here.Groupon's purpose is to build strong communities through thriving small businesses. To learn more about the world's largest local e-commerce marketplace, click here. You can also find out more about us in the latest Groupon news as well as learning about our DEI approach. If all of this sounds like something that's a great fit for you, then click apply and join us on a mission to become the ultimate destination for local experiences and services. Beware of Recruitment Fraud: Groupon follows a merit-based recruitment process without charging job seekers any fees. We've noticed an increase in recruitment fraud, including fake job postings and fraudulent interviews and job offers aimed at stealing personal information or money. Be cautious of individuals falsely representing Groupon's Talent Acquisition team with fake job offers. If you encounter any suspicious job offers or interview calls demanding money, recognize these as scams. Groupon is not responsible for losses from such dealings. For legitimate job openings (and a sneak peek into life at Groupon), always check our official career website at Groupon Careers