ABOUT OUTMARKET
Outmarket is the AI platform for insurance, trusted by more than 250 brokerages to run the work their business depends on. Commercial insurance still runs on dense documents and slow, manual workflows, and that is exactly what we automate: quote comparisons, coverage gap and tower analysis, policy review, and proposal generation, all grounded in our customers’ own data and source-cited so teams can trust the output.
The impact is concrete. Teams save 12 to 15 hours per person every week, cut errors by roughly 65 percent, and win more business, all on infrastructure that is SOC 2 Type II certified, single-tenant, and never used to train AI models. We are an AI-first company in both what we build and how we work, shipping quickly and in close partnership with the agencies that rely on us.
WHAT YOU’LL GET
A high-impact role with ownership from day one.
Competitive compensation and meaningful equity.
Direct collaboration with founders and real users.
Remote-first flexibility.
The opportunity to help build an AI-native product from the ground up.
ABOUT THE ROLE
We are hiring a DevOps Engineer to own the infrastructure and delivery platform that powers our AI products — from cloud infrastructure and CI/CD to the security, reliability, and observability our customers depend on. You will turn infrastructure into code and make safe, fast shipping the default, running the single-tenant, SOC 2 Type II platform that every customer’s trust rests on.
WHY THIS ROLE
Own infrastructure that is core to the product and to customer trust, not a back-office system.
Work on genuinely hard problems: single-tenant isolation, security, and reliability in a regulated industry.
Build the automation, platform, and guardrails that everything we ship depends on.
WHAT WE’RE LOOKING FOR
5+ years operating production infrastructure, hands-on.
Hands-on experience running Kubernetes in production.
Strong Terraform (infrastructure as code) and Python.
CI/CD experience with GitHub Actions.
Deep experience across security, monitoring, reliability, and availability.
Experience with any leading cloud provider (GCP, AWS, or Azure).
AI-first thinking — using AI to build and operate better.
BONUS IF YOU HAVE
Experience with workflow orchestration (e.g., Temporal, Airflow, Dagster).
Experience running single-tenant, SOC 2, or otherwise compliance-sensitive infrastructure.
Exposure to insurance, fintech, or other regulated, data-heavy domains.
