Stephen Heckler
Senior System Engineer at Cloudflare

About

Systems engineer with a focus on customer outcomes, large-scale infrastructure and reliability. At Cloudflare, I help internal and customer-facing teams build more resilient systems and surface failure modes before they reach production. Previously built and operated AWS-based infrastructure at Acumera.

Skills

Reliability & SLOs
  • SLO Design, Tuning, Evangelism
  • Customer-Focused and Internal Reliability
  • Incident Reporting & Review
  • Distributed Systems
  • Synthetic Monitoring
AI & Agents
  • Agent and Skill Development
  • Coding Harness Plugins
  • MCP Integration
Infrastructure
  • Kubernetes: New Cluster Deployment, Operations, Custom Controllers
  • GitOps: ArgoCD, Custom Implementations, Tooling
  • System Admin: Docker, Linux
  • Cloud: AWS, GCP
  • Monitoring: Prometheus, OTel, Tracing
Programming and Configuration Management
  • Terraform
  • CI/CD
  • Go
  • Python
  • TypeScript
  • Salt
  • Ansible
  • Puppet
  • Helm
  • cdk8s

Experience

Cloudflare 6 yrs
Senior Systems Engineer Sep 2025 – Present · 1 yr
Systems Engineer Sep 2020 – Sep 2025 · 5 yrs

Responsible for maintenance and improvement of internal Kubernetes (K8S) clusters, as well as determining Kubernetes user best practices and tooling improvements.

Acumera, Inc. 2 yrs 4 mos
Infrastructure Team Supervisor Jan 2020 – Sep 2020 · 8 mos

Responsible for team planning and strategy while also maintaining contributions as an individual, with a strong focus on reliability and monitoring.

Linux System Administrator Aug 2018 – Jan 2020 · 1 yr 5 mos

Responsible for maintaining cloud-hosted infrastructure, including internal and customer-facing services.

NOC Service Technician May 2018 – Aug 2018 · 3 mos

Responsible for end-to-end troubleshooting remote networks, including routers, switches, and internet connections.

Datroo Technologies 3 mos
Intern Jan 2018 – Apr 2018 · 3 mos

Assisted technicians with maintenance, upgrades, and project rollouts as needed, throughout a variety of environments.

Toro Company 5 mos
Hardware Technician Jul 2017 – Dec 2017 · 5 mos

Built, quality checked, and configured computers and associated peripherals for large-scale irrigation management systems. Focused on increasing efficiency through PowerShell-based automation of computer validation and team processes.