About Sycamore

Sycamore is building the trusted agent operating system for the enterprise. Our platform helps companies build, deploy, and orchestrate agentic apps that take on real operational work, with the security and control large organizations need.

We are a small, engineering-led team working directly with Fortune 500 enterprises. We have raised $65M from Coatue and Lightspeed, along with other investors and industry leaders.

The role

You will build the infrastructure and control-plane software that lets Sycamore's services, mutable development sandboxes, and immutable deployed applications run securely from development through production.

This is software engineering for consequential distributed systems, not cloud administration. You will write control-plane services and Kubernetes controllers, codify infrastructure and delivery paths, design identity and network boundaries, operate tenant-isolated data systems, and debug failures that cross application, cluster, database, and customer-network layers.

You own more than whether a cluster is healthy or a deployment completed. You own whether the system is isolated, observable, recoverable, cost-aware, and safe to change—and whether the next deployment is more repeatable than the last.

Infrastructure is the foundation beneath Product and Core AI. Errors here can affect every application and customer, so we maintain an especially high bar for systems judgment, production ownership, and recovery discipline.

What the work looks like

In one week, you might:

Trace a failed application deployment across artifact creation, image building, registry publication, admission controls, routing, workload identity, health checks, and rollback.

Build or extend a control-plane service or Kubernetes controller that provisions and reconciles tenant or sandbox resources safely.

Design an edge-authentication, service-identity, or delegated-access flow and verify that untrusted workloads cannot cross the boundary.

Investigate latency or reliability across gateways, containers, managed databases, object storage, cluster scheduling, and customer DNS or networks.

Review an infrastructure change for blast radius, execute a staged rollout, watch health signals, and prove the rollback path.

Restore tenant data to a known point, verify the result, and turn the exercise into a repeatable recovery procedure.

Improve sandbox startup time, deployment throughput, resource efficiency, or capacity without weakening isolation.

Work with a customer's infrastructure or security team to satisfy a real deployment constraint, then encode the reusable solution in the platform.

What you will do

Build and operate Kubernetes-based serving and sandbox platforms for agents, internal services, and customer applications.

Develop infrastructure-as-code, Helm charts, provisioning services, admission controls, and operators that reconcile environments safely.

Build deployment systems from versioned artifacts through reproducible image creation, staged rollout, health verification, promotion, and digest-preserving rollback.

Design and debug networking, ingress and edge routing, DNS, TLS, workload identity, secrets, and service-to-service authorization.

Operate tenant-isolated relational databases, object storage, container registries, and deployment metadata.

Own backup, point-in-time recovery, restore verification, regional recovery, capacity planning, and disaster-recovery readiness.

Build observability, SLOs, alerts, capacity controls, and incident-response tooling across clusters, services, sandboxes, and customer workloads.

Maintain production change controls, drift detection, release gates, and fail-safe rollout procedures.

Support hosted and customer-controlled deployment patterns while keeping the operational model consistent and auditable.

Debug complex failures across application code, control planes, containers, Kubernetes, cloud services, databases, identity, and customer networks.

Travel within India when working alongside a customer's engineering or security team will materially improve a deployment or incident outcome.