Chris Montgomery — Systems Hacker & Agentic AI Builder

> cat /etc/identity

Systems-focused engineer who builds in the terminal. Deep expertise in DevOps, SRE, and observability (Datadog), with production experience across Kubernetes, Terraform, and AWS at enterprise scale. I write backend services and CLI tools in Go, build agentic AI systems with multi-agent orchestration, and run everything on Linux with a suckless philosophy. Currently building autonomous agent frameworks, LLM tooling, and observable infrastructure.

> cat stack.yml

Languages: Go, Python, Bash, C, Lua, Rust, TypeScript

Observability: Datadog (APM, RUM, Synthetics, Logs), Prometheus, Grafana

Infrastructure: Terraform, Ansible, Helm, CloudFormation

Containers: Kubernetes (EKS), Docker, cgroups, KVM/QEMU

Cloud: AWS (EC2, ECS, Fargate, RDS, Redshift, IAM, ALB/NLB)

AI / Agents: Multi-agent orchestration, LLM tooling, Claude, Ollama, FastAPI

CI/CD: GitLab CI, GitHub Actions, CircleCI, Docker builds

Systems: Linux (Arch, Ubuntu, CentOS), Neovim, dwm, zsh, rsync, SSH

Networking: TCP/IP, DNS, Service Mesh, OpenVPN, L4/L7 load balancing

Data: PostgreSQL, MySQL (RDS), Redis, RabbitMQ, Redshift

> less experience.log

Site Reliability Engineer & Observability SME 2023 – Present

ECCO Select — embedded with USDA Forest Service (US Public Sector / FedRAMP)

Published Case Study: 60% MTTR Reduction for USDA Forest Service

Led full-stack Datadog observability rollout across 1,000+ VMs and 150+ mission-critical applications on AWS.

60%MTTR Reduction

85%MTTD Improvement

75%APM Deploy Time Drop

150+Apps Monitored

Deployed Datadog across hybrid AWS environments (EC2, ECS, Fargate) with Terraform-managed agent rollouts
Built custom dashboards, monitors, and SLOs; integrated Datadog with ITSM for automated incident ticketing
Implemented APM tracing, synthetic tests, and RUM across 150+ applications
Standardized monitoring-as-code workflows, reducing APM deployment time by 75%
Built dd_lib, a custom Python library for Datadog API automation — abstracting monitor, dashboard, and metric operations into reusable modules
Developed rayne, an agentic root-cause-analysis server that correlates Datadog alerts with infrastructure telemetry to accelerate incident triage
Engineered Python webhook pipelines (client and server) for Datadog event-driven automation — processing monitor alerts, triggering remediation workflows, and forwarding enriched payloads to downstream services
Served as observability SME across teams at varying stages of cloud adoption

DevOps Engineer II Dec 2021 – Aug 2023

St. Louis, MO

Administered Kubernetes (EKS) for 100+ services across production, staging, and services environments
Transitioned clusters from unmanaged to managed nodes; implemented Helm chart standardization across teams
Managed Datadog integration: dashboards, monitors, APM, tracing, and synthetic tests for full-stack observability
Provisioned and managed AWS infrastructure with Terraform: IAM, ACM, EC2, RDS, Redshift, ALB/NLB
Built event-driven and queue-based scaling strategies; developed custom Kubernetes operators
Completed Datadog migration from Grafana/Prometheus; removed Nginx sidecar for internal traffic
Revamped Docker base images from managed packages to compiled-from-source builds, reducing image size and CVEs
Standardized Helm charts from per-service manifests to a unified chart with exceptions
Managed GitLab CI runners, standardized CI files for consistent deployments across developer teams
Administered databases: AWS RDS (MySQL), PostgreSQL (vector DBs), Redshift (warehousing)
Implemented service mesh and L4/L7 load balancing with AWS NLB and ALB

DevOps Engineer Feb 2018 – Dec 2021

CJT Enterprises — Boston, MA

Containerized 3-tier application on Kubernetes: Go frontend, Java REST API, PostgreSQL
Optimized container images with multi-stage builds and Ambassador pattern
Managed CI/CD tooling in Docker on Kubernetes clusters; streamlined Dockerfile creation
Automated server provisioning and configuration with Ansible
Managed SSL certificates for Kubernetes-deployed applications
Administered Linux production environments (Ubuntu, CentOS, Arch)

Aerospace & Propulsion Technician May 2009 – Aug 2012

United States Air Force — East Granby, CT (TF34 & F100 series)

Application Manager — Assistant Vice President Feb 2015 – Nov 2018

State Street Corporation — Boston, MA (Leadership Development Program)