Engineering Manager for Observability/CI/CD and Cloud

Groupon is transforming its platform with AI at its core, seeking a hands-on Engineering Manager for Observability and CI/CD. This strategic role involves leading a globally distributed team of 5-10 engineers, modernizing core infrastructure from legacy systems (Jenkins, ELK) to cloud-native solutions (GitHub Actions, GCP Logging, Prometheus/Grafana). The manager will operationalize AI tools for engineering workflows, architect and optimize a hybrid tech stack (Kubernetes, Envoy, Terraform, GCP, AWS), and drive strategic projects with direct business impact, ensuring scalable, reliable, and cost-efficient platforms.

Must Have

• Lead and mentor a globally distributed team of CI/CD and Observability engineers.
• Modernize core infrastructure from legacy to cloud-native solutions (GitHub Actions, GCP Logging, Prometheus/Grafana).
• Operationalize AI tools for engineering workflows, including log analysis and automated infrastructure as code.
• Oversee and optimize a hybrid tech stack (Kubernetes, Envoy, Terraform, GCP, AWS).
• Drive strategic projects with tight deadlines and direct business impact, such as Jenkins-to-GHA and ELK-to-GCP migrations.
• Possess 5+ years’ experience leading infrastructure, DevOps, or SRE teams (5+ people).
• Demonstrate deep technical expertise in cloud-native platforms, observability, infrastructure as code, and CI/CD tooling.
• Proven success operationalizing AI tools within engineering workflows for real-world impact.

Good to Have

• 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.

Perks & Benefits

• 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.

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.

Groupon is an AI-First Company

We’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.