Senior/Lead DevOps (Platform Tooling) Engineer

Upwork ($UPWK) is the world’s work marketplace. We serve everyone, from one-person startups to over 30% of the Fortune 100, with a powerful, trust-driven platform that enables companies and talent to work together in new ways that unlock their potential.

Last year, more than $3.8 billion of work was done through Upwork by skilled professionals who are gaining more control by finding work they are passionate about and innovating their careers.

This is an engagement through Upwork’s Hybrid Workforce Solutions (HWS) Team. Our Hybrid Workforce Solutions Team is a global group of professionals that support Upwork’s business. Our HWS team members are located all over the world.

Work/Project Scope:

Are you a seasoned DevOps engineer with a passion for solving complex problems and integrating diverse technologies? Do you thrive in dynamic environments where your ideas are valued, and you can make a real impact? Upwork is seeking a Senior Platform Tooling Engineer to join our Platform Engineering team. In this role, you'll be pivotal in supporting both our core Marketplace business and our rapidly expanding AI and Machine Learning business unit, Umami. You'll have the opportunity to work at scale — managing thousands of microservices and tens of thousands of builds per week — while shaping the next generation of our platform using the latest Cloud Native technologies.

Team Description

The Platform Engineering team at Upwork is at the heart of our technology ecosystem, supporting every step of the software development life cycle (SDLC) for hundreds of microservices — from development and release to deployment and runtime operation. Our team is passionate about building systems that integrate various technologies seamlessly, ensuring that our internal customers — hundreds of product engineers — can work efficiently and effectively.

We are a tight-knit team of eight engineers divided into two squads:

• CI/CD Squad: Focused on continuous integration and delivery, managing tools like Jenkins, Tekton, and our migration to GitHub Actions.

• Developer Portal Squad: Centered around improving developer experience using platforms like Backstage and automating workflows with Argo Workflows and Kubernetes.

We value initiative, collaboration, and the freedom to innovate. At Upwork, everyone has the opportunity to propose solutions and contribute meaningfully without unnecessary hierarchy.

Key Responsibilities

• Design and Implement CI/CD Pipelines: Collaborate with cross-functional teams to design, implement, and maintain CI/CD pipelines using Jenkins, Tekton, and GitHub Actions.

• Migration to GitHub Actions: Lead the migration of thousands of pipelines and microservices to GitHub Actions, ensuring minimal disruption and enhanced efficiency.

• On-Call Support: Provide on-call support during Pacific Time Zone business hours (9 AM - 6 PM PT) to address incidents, troubleshoot issues, and assist our AI/ML business unit with their unique technical requirements.

• Automation and Integration: Develop automation workflows using Argo Workflows and Kubernetes, integrating various technologies to create cohesive and efficient systems.

• Customer-Centric Engineering: Engage with internal stakeholders to understand their needs, set expectations, and deliver solutions with empathy and clear communication.

• Platform Development: Contribute to both the maintenance of our existing platform and the development of our new platform based on modern Cloud Native principles.

• Best Practices and Compliance: Uphold best practices in DevOps, ensure security compliance, and promote infrastructure as code using Terraform.

What We Offer

• Impact at Scale: Work on an infrastructure that supports over 40,000 builds per week, hundreds of microservices and a large engineering community.

• Innovation and Freedom: An open environment where your ideas can drive real change without unnecessary bureaucracy.

• Complex Challenges: Tackle interesting technical challenges that require integrating multiple technologies and thinking creatively to find effective solutions.

• Collaborative Culture: Join a team of experienced engineers who are passionate about what they do and are always willing to help.

• Transformative Contributions: Your efforts will directly enhance the productivity of hundreds of engineers and support the growth of Upwork's business units, including cutting-edge AI/ML projects.

Must-Have Qualifications

• Extensive DevOps Experience: Minimum of 5 years in DevOps or Platform Engineering roles, with a strong focus on CI/CD pipelines and automation.

• AWS Expertise: Deep understanding and hands-on experience with AWS services, including IAM, ECR, S3, RDS, and EKS.

• Docker and Kubernetes Proficiency: Proven experience deploying and managing applications in Kubernetes environments, especially using AWS EKS.

• CI/CD Tools Mastery: Hands-on experience with Jenkins, Tekton, and GitHub Actions; ability to design and maintain complex CI/CD pipelines.

• Infrastructure as Code: Proficient with Terraform for infrastructure automation and management.

• Programming Skills: Proficiency in Python and at least one of Java or JavaScript/TypeScript for automation scripting and workflow development.

• Problem-Solving Mindset: Ability to think in terms of system design and integration, envisioning how components interact and impact each other.

• Excellent Communication: Strong customer-centric approach with the ability to communicate effectively, set expectations, and collaborate with internal teams.

• Time Zone Availability: Must be available to work 9 AM - 6 PM Pacific Time to support teams located on the US West Coast.

Nice-to-Have Qualifications

• Argo Workflows and ArgoCD: Experience designing and implementing workflows using Argo technologies.

• Backstage Knowledge: Familiarity with extending or integrating Backstage developer portals.

• HashiCorp Vault and JFrog Artifactory: Experience with secrets management and artifact repositories.

• Crossplane Experience: Knowledge of Crossplane for infrastructure management.

• Monitoring Tools: Experience with Grafana, Prometheus, and other monitoring and logging tools.

• Large-Scale Environment Experience: Previous work in environments with similar scale and complexity.

If you are ready to take on this exciting challenge and help us build the future of our platform, we'd love to hear from you! Please submit your resume, and if you’d like, include a cover letter that highlights your relevant experience and explains why you would be a great fit for this role.

Upwork is proudly committed to fostering a diverse and inclusive workforce. We never discriminate based on race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical condition), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics.   

Additionally, a criminal background check may be run on a candidate after a conditional offer to perform your services for Upwork is made. Qualified applicants with arrest or conviction records will be considered in accordance with applicable law, including the California Fair Chance Act and local Fair Chance ordinances.