Senior Cloud Infrastructure Engineer

Judgment Labs builds infrastructure for Agent Behavior Monitoring (ABM). While traditional observability focuses on logging exceptions and latency, our ABM surfaces behavioral anomalies such as instruction drifts and context retrieval loss in scaled production environments.

Hundreds of teams building autonomous agents rely on Judgment to understand how their systems are behaving post-deployment. Instead of reactive incident triage, they cluster patterns across conversations and workflows, correlate regressions to specific interaction types, and pinpoint where reliability breaks down in their usage context.

We’ve raised $30M+ across two rounds in the past five months. Our investors include Lightspeed, SV Angel, Valor Equity Partners, Nova Global, Chris Manning, Michael Ovitz, Michael Abbott, Cory Levy, Kevin Hartz, and others.

The Role:

We are looking for a Senior Cloud Infrastructure Engineer to architect and scale the deployment infrastructure that powers agent behavior monitoring at production scale. This role is crucial for enabling enterprise customers to run Judgment in their environments—whether that's multi-region cloud, self-hosted, or BYOC deployments—while maintaining the security, compliance, and reliability standards they require. We need someone who has built distributed systems that handle real production traffic and can own infrastructure from architecture through operations.

What You'll Do:

• Design and implement multi-region cloud architecture with automatic failover and disaster recovery across AWS, GCP, and Azure.

• Architect and deploy regional compliance solutions (data residency, sovereignty) for enterprise customers in different geographies.

• Design and implement self-hosted and BYOC (Bring Your Own Cloud) deployment architectures for enterprise customers with strict security requirements.

• Build secure VPC peering and private connectivity solutions for customer-managed environments

• Develop automated provisioning systems for on-premises and hybrid cloud deployments

• Create customer-facing documentation and deployment guides for self-service infrastructure setup

• Design enterprise-grade security architectures including network isolation, encryption at rest and in transit, and identity management integration (SSO, SAML, SCIM).

• Build monitoring and observability solutions for distributed self-hosted deployments with centralized logging and alerting.

What We're Looking For:

• Deep expertise across multiple cloud platforms (AWS, GCP, Azure) including compute, networking, storage, and managed services

• Experience designing and operating multi-region, highly available cloud infrastructure

• Strong knowledge of cloud networking (VPCs, load balancers, DNS, CDN, service mesh)

• Expertise in Infrastructure as Code (Terraform, Pulumi, CloudFormation) and GitOps practices

• Experience with self-hosted deployments and BYOC architectures, including customer environment setup and lifecycle management

• Design and implement secure network architectures for customer-managed cloud accounts and on-premises environments

• Build automation for provisioning, upgrades, and maintenance in customer-controlled infrastructure

• Senior-level ownership: you will own infrastructure roadmap, architecture design, set practices, identify bottlenecks, ship fixes.

Nice to have:

• Experience with air-gapped and restricted network environments

• Knowledge of private connectivity solutions (AWS PrivateLink, Azure Private Link, GCP Private Service Connect)

• Familiarity with enterprise security requirements including SOC 2, ISO 27001, HIPAA, and FedRAMP compliance frameworks

Target Profile:

• Senior Infrastructure Engineer from observability company (Datadog/Sentry/Honeycomb), Enterprise AI startups (Harvey, Glean), Infrastructure SaaS (Databricks/Snowflake)

Why Judgment?

• Agents can’t work without this. Today’s agents hallucinate, drift, and break in production. We’re building the infrastructure that fixes this: the monitoring layer that makes agents self-improving.

• We’re wired to win. We're a team of less than 20 but we ship like 50+ on the daily. You'll be working with olympiad medalists, debate champions, and competitive athletes who bring that same intensity to company building.

• Fast track to founding. Our engineers interface directly with customers, ship code into their environments, and use their feedback to dictate what’s next on the roadmap. Everyone on the team is either an ex-founder or a founder-to-be.

• We make sure our people do their best work. If you deserve a spot on the team, money will never get in the way of it. Full benefits, Equinox, and a private chef to take care of you. We sprint hard but we play hard, ask us about our Smash/Mario Kart tournaments.

We work in person in San Francisco.