Stephen Heckler
Senior System Engineer at Cloudflare

About

Systems engineer with a focus on large-scale infrastructure and reliability. At Cloudflare, I help internal 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
  • SLO Evangelization
  • Customer Reliability
  • Incident Review
  • Distributed Systems
AI & Agents
  • Agent Development
  • Coding Agent Plugins
  • MCP Integration
  • Local & Remote Tooling
Infrastructure
  • Kubernetes
  • Linux
  • AWS
  • Terraform
  • CI/CD
  • Go
  • Python
  • TypeScript
  • Configuration Management (Salt/Ansible/Puppet)

Experience

Cloudflare 5 yrs 9 mos
Senior System Engineer Sep 2025 – Present · 9 mos

Helping teams build reliable systems and uncover systemic flaws, with a focus on championing customer reliability and monitoring.

Systems Engineer Sep 2020 – Sep 2025 · 5 yrs

Maintaining, improving, and expanding our internal Kubernetes platform through operational tasks, long term architectural improvements, and developer tooling development.

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

Responsible for IT support staff, as well as AWS Sysadmin, in addition to leading infrastructure improvement/expansion efforts.

Linux System Administrator Sep 2018 – Jan 2020 · 1 yr 4 mos

Maintain and improve AWS-based internal infrastructure, support development team, and assist with new product rollouts.

NOC Service Technician May 2018 – Sep 2018 · 4 mos