5+ years * AWS + On-Prem

Steven Rupert

Senior DevOps Engineer

Cloud Infrastructure Automation Reliability

Senior DevOps Engineer with 5+ years of experience operating and automating production systems across AWS and on-prem environments.

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Core Competencies

cloud
Cloud & Platform Operations
AWS, VMware vSphere 7-8, on-prem and hybrid systems
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Infrastructure as Code
Terraform, Ansible, Packer
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CI/CD & Delivery
Jenkins pipelines, Git review workflows, release automation
monitoring
Observability
Datadog metrics, logs, alerting, and on-call operations

Philosophy

01_PRINCIPLES
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Automation First

If it happens twice, automate it. Infrastructure should be predictable, versioned, and reproducible.

security

Reliability Focused

Production operations are part of engineering. Monitoring quality and actionable alerting matter as much as deployment speed.

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Security by Baseline

IAM, network controls, and consistent hardening are treated as default platform requirements, not post-release tasks.

Experience

02_EXPERIENCE
2020 — 2026

Senior DevOps Engineer

Kajeet, Inc.

  • 01

    Designed, deployed, and operated production infrastructure across AWS and on-prem environments supporting Dev, QA, Staging, and Production workloads.

  • 02

    Developed and maintained Ansible automation for security agents, monitoring agents, OS updates, and internal reporting; refactored legacy automation to reduce configuration drift.

  • 03

    Designed and deployed Ansible Automation Platform (AAP) with LDAP/Active Directory integration, centralizing recurring production automation previously executed from engineer workstations.

  • 04

    Built a greenfield Terraform codebase for vSphere, automating production workload provisioning across two datacenters and multiple environments and reducing delivery time from days to hours.

  • 05

    Led time-critical vSphere/VxRail infrastructure consolidation, migrating ~37–40 VMs with associated PowerStore iSCSI storage and port group dependencies in under 8 working hours with no production downtime, avoiding a six-figure annual licensing cost.

  • 06

    Maintained Terraform-managed AWS infrastructure across Dev, QA, Staging, and Production using Jenkins-driven plan/apply workflows, remote state, and Git review gates.

  • 07

    Served as SME across virtualization, automation, observability, and storage domains; supported production systems in a 4-person on-call rotation and reduced alert fatigue through Datadog monitor tuning.

AWS VMware vSphere Terraform Ansible Packer Jenkins Datadog Python Kubernetes
Personal

Open Source / Personal Projects

Independent technical work

Cloud Resume Platform

  • 01

    Designed and deployed this resume platform as a production-style cloud project using GCP, Terraform, Ansible, Docker, Cloudflare, and Datadog.

  • 02

    Implemented automated CI/CD with GitHub Actions for testing, container builds, Terraform deployment, and Ansible-based application release workflows.

  • 03

    Built secure ingress and observability around the platform, including Cloudflare proxying, TLS, structured logs, metrics, APM, and uptime/SLO monitoring.

GCP Terraform Ansible Docker GitHub Actions Cloudflare Datadog Python Flask

XCP-ng Packer Plugin Contribution

Open Source Packer XCP-ng XenServer

Capability Stack

03_SKILLS
PLATFORMS
AWS
VMware vSphere 7-8
Hybrid On-Prem/Cloud
PROVISIONING
Terraform
Ansible
Packer
RUNTIME
Linux (Ubuntu, RHEL)
Containers
Kubernetes
TOOLING
Jenkins
Datadog
Python / Bash
Foundational Logic

Education

Formal training in networking and cybersecurity, backed by hands-on infrastructure operations and automation experience.

B.S. Computer Networks & Cybersecurity, University of Maryland Global Campus (2020)
A.A.S. Information Services Technology, College of Southern Maryland (2018)