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About Bespoke Labs
Bespoke Labs is an AI research and data company building the datasets, benchmarks, and evaluation infrastructure that power frontier AI models. We're backed by leading investors, trusted by top AI labs, and have research accepted at venues like ICLR 2026. Our team is small, moves fast, and has an outsized impact on how the next generation of AI is built.
The Role
We're looking for a mid-level DevOps / Site Reliability Engineer to own and scale our cloud infrastructure. You'll work closely with engineering and ML teams to keep our systems reliable, observable, and fast — directly supporting the infrastructure that powers AI data pipelines at scale.
What You'll Do
Own cloud infrastructure on AWS — EC2, EKS, RDS, S3, IAM, VPC
Manage Kubernetes clusters and container orchestration end-to-end
Build and maintain CI/CD pipelines using GitHub Actions or similar
Implement monitoring, alerting, and observability stacks (Prometheus, Grafana, or DataDog)
Improve reliability, performance, and security of production systems
Automate infrastructure with Terraform or similar IaC tools
Debug and resolve issues across complex, distributed systems
Participate in design reviews and help raise the infrastructure bar
What We're Looking For
3–5 years in DevOps, SRE, or infrastructure engineering
Strong AWS experience — EKS, EC2, RDS, S3, IAM
Kubernetes — deployment, scaling, troubleshooting in production
CI/CD pipelines — GitHub Actions, ArgoCD, or similar
Infrastructure as Code — Terraform, Pulumi, or CDK
Python or Go scripting
Experience working in production environments with real users
Comfort with ambiguity and ability to operate autonomously
Nice to Have
Experience supporting ML training workloads or GPU clusters
Familiarity with distributed computing or large-scale data pipelines
Prior work at an AI, ML, or data company
Open-source contributions or published technical writing
What We Offer
Competitive compensation and meaningful equity
Direct impact on frontier AI model training and evaluation infrastructure
Flexible, remote-friendly environment with low bureaucracy
A small, high-caliber team with deep AI research expertise
Health, wellness, and learning & development benefits
What you need to know about the Chicago Tech Scene
Key Facts About Chicago Tech
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- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
