Senior Site Reliability Engineer · Chicago, IL
10 years of experience combining deep networking with modern cloud platform engineering. I operate Instructure's multi-region Kubernetes platform, powering Canvas LMS for tens of millions of learners worldwide, and I'm known for owning multi-region migrations end-to-end and building the reusable infrastructure application teams build on.
Built "Trigger," Instructure's internal developer platform powering Canvas LMS across 40 EKS clusters in 8 AWS regions with 433 active service deployments on Akuity-managed ArgoCD GitOps, Helm/Kustomize, and Kyverno policy-as-code. Now building Trigger's next-generation deployment API on Node.js/Express and MongoDB, replacing the legacy internal PaaS it runs on.
Migrated to AppGate ZTNA to replace scattered SSH keys, a legacy Teleport VPN, and the GlobalProtect client VPN, eliminating the HQ routing bottleneck. Also rolled out ArgoCD Okta SSO via SCIM and HashiCorp Vault, giving every engineer centrally managed, auditable access.
Architected and built Instructure's AWS Transit Gateway mesh with Terraform and Ruby, migrating off a self-hosted VyOS mesh running iBGP and OSPF with zero customer downtime. The new mesh has held five-nines uptime since cutover. Also led a fleet-wide TGW security-group referencing rollout across 34 TGWs in 9 regions, trimming thousands of CIDR-based rules.
Designed org-wide security tooling, including CrowdStrike CSPM, Wiz, and AWS Config StackSets. When that tooling caught an active post-compromise incident, used it to trace what changed and tuned AWS WAF rules in real time to contain the attack, then led the migration to Signal Sciences for longer-term WAF coverage.
Own observability and CI/CD strategy, spanning Datadog/Observe dashboards, GitHub/Gerrit for version control, and Jenkins/GitHub Actions pipelines that give every team a paved-road way to ship and debug safely. Architected network/IAM for new AWS LZA accounts end-to-end, replacing one-off account requests with a group-based access model every team onboards through.