At the Workers Benefit Fund, we are always seeking experienced and innovative team members who are passionate about leveling the playing field for everyone in the new gig economy workforce. Our goal is to give access & provide benefits to these 100 million-strong non-traditional workers who don't have access to corporate benefit plans or traditional benefits. We are passionate about building tools & services to re-envision what is possible for gig workers.
As a Senior DevOps Engineer, you will play a critical role in architecting, scaling, and securing the infrastructure that powers these products. This is a senior technical position for someone who thrives in ownership, drives infrastructure strategy, and enjoys mentoring teammates while solving complex reliability challenges.
Job Brief
We are looking for an experienced DevOps professional (5-8+ years) who can own end-to-end reliability, design large-scale infrastructure, and guide the team in DevOps best practices. You should be comfortable making architectural decisions, leading migrations, and being the point person during major incidents.
Responsibilities:
- Design and evolve high-level AWS infrastructure architecture, including multi-region deployments, high availability, and disaster recovery strategies.
- Own and drive AWS best practices for security, networking, compute, storage, and managed services across the organization.
- Lead and execute major platform migrations, infrastructure upgrades, and modernization initiatives.
- Act as the senior point of escalation during critical incidents, coordinating real-time response and leading postmortem processes.
- Improve and maintain GitLab CI/CD pipelines, deployment workflows, and automation tooling.
- Develop internal tools and automation to reduce operational overhead, prevent recurring issues, and improve developer experience.
- Ensure performance, scalability, and reliability of production environments supporting WBF's core products.
- Conduct deep root-cause analysis and implement long-term corrective actions for system-wide issues.
- Mentor and support the growth of mid-level and junior DevOps engineers through guidance, reviews, and hands-on coaching.
- Collaborate closely with engineering, data, and product teams to guide infrastructure decisions and roadmap planning.
- Proactively identify improvements to infrastructure, architecture, operations, and deployment workflows, with autonomy to implement changes.
Current Qualifications and areas to improve
- Excellent English verbal and written communications skills (advanced)
- Strong production experience with
AWS
, with deep expertise in
EKS
.
- Solid understanding of VPC design, networking, IAM, autoscaling strategies, and cost-aware architecture.
- Experience designing, operating, and scaling cloud infrastructure in production environments.
- Advanced experience with
Kubernetes (EKS)
, including cluster operations, upgrades, and troubleshooting.
- Proficiency with
Helm
for application packaging and deployments.
- Strong hands-on experience with Terraform for Infrastructure-as-Code across AWS and Kubernetes resources.
- Advanced experience building and maintaining CI/CD pipelines, runners, and deployment automation.
- Infrastructure Monitoring: Prometheus/Grafana/Loki Stack
- Strong scripting skills using Python and/or Bash for automation and tooling.
- Experience leading incident response, writing clear postmortems, and driving root-cause analysis (RCA).
- Familiarity with cloud-native security practices, including identity and permissions management, vulnerability scanning, and compliance considerations.
- Experience mentoring or leading other engineers
- Problem-solving attitude
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