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Outmarket is an AI platform for commercial insurance that automates quote comparisons, coverage analysis, policy review, and proposal generation. The company serves 250+ brokerages and helps teams save 12-15 hours per week while reducing errors by ~65%. The platform is SOC 2 Type II certified, single-tenant, and never used to train AI models.
As DevOps Engineer, you will own the infrastructure and delivery platform powering Outmarket's AI products. Your responsibilities include managing cloud infrastructure, CI/CD pipelines, security, reliability, and observability systems. You'll translate infrastructure into code, establish safe and fast shipping practices, and maintain the single-tenant, compliance-sensitive platform that customers depend on.
Key responsibilities:
- Design and operate production Kubernetes clusters in a regulated environment
- Build infrastructure-as-code using Terraform across cloud providers (GCP, AWS, or Azure)
- Establish and maintain CI/CD pipelines using GitHub Actions
- Implement security, monitoring, reliability, and availability best practices
- Solve hard problems around single-tenant isolation and compliance in insurance
- Create automation and guardrails that enable safe, rapid shipping
- Collaborate directly with founders and customers
Required qualifications:
- 5+ years hands-on production infrastructure experience
- Production Kubernetes expertise
- Strong Terraform and Python skills
- GitHub Actions CI/CD experience
- Deep knowledge of security, monitoring, reliability, and availability
- Experience with at least one major cloud provider
- AI-first mindset and ability to leverage AI in infrastructure work
Bonus experience includes workflow orchestration (Temporal, Airflow, Dagster), single-tenant or SOC 2 infrastructure, and exposure to insurance, fintech, or regulated data-heavy domains.
