Infrastructure as Code at Scale
Building and managing enterprise Terraform platforms with automated compliance and self-service provisioning across multiple teams and environments.
Jacob Wilson
Site Reliability Engineer
Here to make things work better (and have fun doing it)
Available for opportunities
Available for:
- Full-time SRE/Platform roles
- Consulting, collaboration, and coffee recommendations
Usually responds within 24 hours
Based in Chicago, IL
About
I'm a Senior Site Reliability Engineer focused on infrastructure automation, developer experience, and observability. I build systems that are secure, scalable, and easy to operate, and I enjoy mentoring engineers along the way.
New to Chicago and loving it. Outside of work, you'll find me at the gym, tinkering with home automation projects, or diving deep into AI. I believe the best systems are built with curiosity and a willingness to break things.
Focus areas
Compliance Automation
Implementing SOX and ITGC controls as code, with automated checks, audit trails, and secrets rotation across cloud platforms.
Platform Observability
Datadog, Prometheus, and Grafana monitoring for IaC tooling, Kubernetes platforms, and cloud infrastructure with proactive alerting.
Documentation & Enablement
Creating comprehensive guides and onboarding programs that accelerate team adoption and reduce operational overhead.
Tech Stack
Cloud & Infrastructure
Observability & Monitoring
Tools & Automation
Compliance & Security
Experience
Key Projects & Impact
GitHub Enterprise SOX Compliance
Led as PM and developer to implement automated branch protections across enterprise-scale repository management, delivering on tight audit timeline and preventing compliance deficiency
Infrastructure as Code at Scale
Migrated hundreds of repositories from manual management to Terraform, enabling compliant self-service while maintaining security controls
Cloud Infrastructure Modules
Developed production-ready Terraform modules for cloud services, used across multiple teams and environments
IaC Platform Monitoring
Implemented Datadog monitoring for platform runners and deployment pipelines, improving platform reliability and incident response
Documentation & Enablement
Created comprehensive onboarding guides for multiple platforms, reducing time-to-productivity for new team members
Platform Migration
Led migration of 100+ monitoring alerts to new collaboration platform, updating infrastructure modules and creating migration documentation
- Led SOX compliance initiative as PM and developer to bring GitHub Enterprise into compliance, implementing automated branch protection controls across enterprise-scale repository management, preventing potential company-wide audit deficiency.
- Architected and deployed Infrastructure as Code platform managing hundreds of repositories with Terraform, implementing automated compliance checks and self-service provisioning that reduced environment setup.
- Developed production-ready Terraform modules for cloud services, enabling compliant, repeatable deployments across development, staging, and production environments.
- Built comprehensive monitoring for IaC tooling using Datadog, implementing proactive alerts for platform runners and deployment pipelines, improving platform reliability and reducing MTTR.
- Led migration of 100+ monitoring alerts to new collaboration platform, updating Terraform modules and creating migration guides to support company-wide platform transition.
Observability Platform Impact
Incident Response
Established on-call rotation and runbook system
SLO Framework
Defined SLIs/SLOs for 10+ critical services with automated tracking
- Helped form the SRE team and established SLOs and monitoring practices, improving MTTR by 40% through better incident detection.
- Led deployment of enterprise observability tooling for monitoring and alerting, providing visibility across 100+ microservices.
- Delivered stacks with Prometheus, Thanos, Jaeger, and Dynatrace, reducing alert noise by 65% through improved signal-to-noise ratio.
- Partnered with engineering and infrastructure to ship a commercial application.
- Built monitoring, alerting, and automation for performance improvements.
- Led Grafana adoption with real-time insights on usage and performance.
- Database, desktop, network, and Windows infrastructure rotations.
- Deployed Graylog, supported Exadata/Postgres/MongoDB troubleshooting.
- Managed enterprise OS changes and endpoint tooling (Jamf, SCCM).
- Implemented network traffic prioritization and datacenter upgrades.
Resume
The full resume includes detailed project scope, technical achievements, and education history.
Education
B.S. Information Technology, Network/Systems Focus
University of Cincinnati
Let’s talk
I’m always open to meaningful collaborations, new challenges, and friendly conversations.
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