JACOB WILSON Senior Site Reliability Engineer · Platform Engineering jacob@jacobwilson.net | jacobwilson.net | linkedin.com/in/jacob-wilsonnet | Chicago, IL ================================================================================ SUMMARY ================================================================================ Senior Site Reliability Engineer with ten years in infrastructure and operations, focused on platform engineering in a regulated healthcare environment (SOX, HIPAA, SOC 2). Builds self-service developer platforms, infrastructure as code and compliance automation that let application teams ship on their own and stay audit-ready without slowing down. Hands-on with Terraform, Kubernetes, Azure and GitHub Actions, writing the Python and TypeScript that ties them together. ================================================================================ EXPERIENCE ================================================================================ SENIOR SITE RELIABILITY ENGINEER | CoverMyMeds (McKesson) May 2022 – Present | Columbus, OH (Remote) Platform engineering team for a healthcare technology company. Build and run the internal developer platform that application teams use to create, deploy and operate services. Self-service developer platform: * Co-built a self-service golden path that lets application teams set up a repository, infrastructure, cloud identity, database access and deployments themselves, removing manual steps from the process. Built its workflow orchestrator and provisioning forms for the July 2026 launch, from development through production. [METRIC?: onboarding time before → after, or number of teams/apps onboarded] * Ran the evaluation and wrote the migration plan for consolidating the developer portal onto a commercial internal developer portal, including a proof of concept and a gap analysis. Security & compliance automation: * Found a gap in the ITGC program-change process that made it hard to follow, and built a Python service on my own initiative to close it. It checks production change tickets against audit requirements so developers and managers get changes right and avoid audit findings. Now used broadly across CoverMyMeds' engineering organization. * Moved SOX/ITGC controls from manual review into enforced CI/CD automation: separation of duties on production deploys, least-privilege infrastructure apply, isolated compliance workflows, and a single scanned pipeline as the only route to publish artifacts. [METRIC?: manual review hours or audit findings removed] * Led GitHub Enterprise SOX compliance as project manager and developer, rolling out automated branch protection across the organization's repositories on a tight audit timeline. * Integrated GitHub Advanced Security into delivery pipelines ahead of a company-wide DevSecOps deadline. * Supported two annual SOX audit cycles with evidence and secret rotations. Moved privileged access to dedicated admin accounts under enterprise SSO, and replaced long-lived personal access tokens with short-lived tokens and GitHub Apps. AI-assisted engineering: * Led AI-assisted engineering adoption on the platform team: agent context files across all platform repositories, MCP access to observability data, and a shared library of skills, hooks and subagents, packaged as plugins, that engineers install and contribute to, including skills that encode platform runbooks such as path-to-production status checks and access-token reviews. * Set up the guardrails for rolling AI coding tools out to the team: managed settings and permission rules, an opt-in usage dashboard, and the team's AI best-practices guide. * Built AI assistants for platform work: retrieval over platform docs and runbooks so answers come from the team's own knowledge, an onboarding triage assistant in Microsoft Teams, and an agent that automates pre-standup triage. Infrastructure as code: * Brought hundreds of GitHub repositories [METRIC?: exact count] under Terraform, replacing manual configuration with reviewed, auditable code. * Administer both Terraform Enterprise and HCP Terraform. Designed the HCP Terraform access model and wrote its self-service onboarding guide, the most-read document I have written. * Built reusable Terraform modules for Azure services, including Azure Managed Redis with passwordless authentication, with a reference implementation and runbook so other teams could adopt them without help. [METRIC?: number of teams or services using the modules] Reliability & operations: * Operated production AKS clusters, including version upgrades, autoscaling and Vault-to-Kubernetes secrets integration. Served as on-call primary and ran weekly on-call retrospectives. * Owned upgrades and lifecycle for core developer tooling, including GitHub Enterprise Server. Centralized audit logging in Splunk and retired legacy automation tooling. * Built Datadog monitoring for infrastructure-as-code runners and deployment pipelines, and moved 100+ alerts from Slack to Microsoft Teams ahead of the company's Slack retirement. Built a chatbot workflow for incident response in Teams. Team leadership: * Mentor new hires and junior SREs, from their first weeks at the company through day-to-day work. * A main code reviewer for the team's infrastructure changes. Started and ran a weekly hands-on upskilling program for engineers, and introduced team flow practices such as WIP limits. SENIOR SITE RELIABILITY ENGINEER | 84.51° (The Kroger Co.) November 2019 – May 2022 | Cincinnati, OH * Helped found the SRE team and brought in SRE ways of working: on-call, runbooks, SLIs and SLOs for 10+ critical services, and leading root-cause analysis on major incidents. Cut mean time to recovery by 40%. * Led the rollout of enterprise observability across 100+ microservices, with an automated Ansible pipeline to deploy Prometheus, Thanos and Jaeger, and integration with Dynatrace. Cut alert noise by 65%. * Built and maintained server- and application-level monitoring with Grafana, Prometheus exporters and Dynatrace, giving teams day-to-day visibility into operations and issues. VERSATILIST ENGINEER | 84.51° (The Kroger Co.) June 2018 – November 2019 | Cincinnati, OH * Main liaison between an engineering team and the infrastructure teams, driving and supporting the release of the company's main commercial application. * Led the rollout of Grafana Enterprise and built real-time dashboards on the application's usage and performance that the business used for decisions. * Helped roll out application performance monitoring (APM) so developers could troubleshoot and understand their applications faster. INFORMATION TECHNOLOGY CO-OP | 84.51° (The Kroger Co.) May 2016 – May 2018 | Cincinnati, OH * Rotations across database, network, desktop and Windows infrastructure: deployed Graylog for log management, supported database troubleshooting (Exadata, PostgreSQL, MongoDB), and managed OS changes and endpoint tooling (Jamf, SCCM). * Deployed and maintained network equipment in offices and datacenters, including traffic prioritization and datacenter upgrades. ================================================================================ SKILLS ================================================================================ Platform & Infrastructure as Code: Terraform, HCP Terraform, reusable module design, internal developer platforms / golden paths, Backstage, developer experience (DX) and DORA metrics Cloud & Kubernetes: Microsoft Azure, provisioned and managed as code with Terraform: networking (virtual networks, private endpoints, DNS), AKS, Managed & Workload Identity, Key Vault, Azure Managed Redis, Azure Database for PostgreSQL · Kubernetes, Helm, Docker Security & Compliance: SOX / ITGC controls as code, HIPAA, SOC 2, GitHub Advanced Security, HashiCorp Vault, Okta / SSO, least-privilege access, secrets rotation AI-Assisted Engineering: Claude Code (skills, hooks, subagents, plugins), Model Context Protocol (MCP), AI agents, retrieval-augmented generation (RAG), AI tool governance, AI usage monitoring CI/CD & GitOps: GitHub Actions, GitHub Enterprise, Argo CD, Jenkins, JFrog Artifactory Observability & Reliability: Datadog, OpenTelemetry, Prometheus, Grafana, Splunk, SLOs / SLIs, incident response, on-call Languages: Python, TypeScript / Node.js, Bash, HCL ================================================================================ EDUCATION ================================================================================ B.S. Information Technology, Network/Systems Focus | University of Cincinnati | 2014 – 2019