jacobwilson.net / status
Jacob Wilson

Jacob Wilson

Senior Site Reliability Engineer · Platform engineering · Chicago, IL

Career uptime

May 2016 — today 126 months in operations · hover or tap a bar
IT co-op · 84.51° Versatilist engineer · 84.51° Senior SRE · 84.51° / Kroger Senior SRE · CoverMyMeds / McKesson

Components

Self-service developer platform

Golden paths that let application teams get a repo, infrastructure, identity, database access and a deploy, with the manual steps removed.

Operational

Security & compliance automation

SOX controls enforced by the pipeline instead of manual review, in a SOX-, HIPAA- and SOC 2-regulated environment.

Operational

AI-assisted engineering

Shared skills, hooks and MCP integrations, with guardrails and usage tracking, that make AI tools useful on real platform work.

Operational

Infrastructure as code

Terraform and HCP Terraform at organization scale, with reusable modules other teams adopt on their own.

Operational

Reliability & observability

Kubernetes in production, SLOs, on-call, and alerts that mean something.

Operational

Incident history

ResolvedCoverMyMeds · 2026

Starting a new service took manual steps across teams

Co-built a self-service golden path: application teams now set up a repository, infrastructure, cloud identity, database access and deployments themselves, with the manual steps removed. I built its workflow orchestrator and provisioning forms, from development through production, and ran the evaluation and migration plan for moving our developer portal to a commercial one.

ResolvedCoverMyMeds · 2026

A program-change process that was hard to follow correctly

I found a gap in our 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. It’s now used broadly across CoverMyMeds’ engineering organization.

ResolvedCoverMyMeds · 2023 — now

Audit controls that depended on manual review

Moved SOX controls into CI/CD so the pipeline enforces them: separation of duties on production deploys, least-privilege infrastructure apply, isolated compliance workflows, and one scanned pipeline as the only way to publish artifacts. Integrated GitHub Advanced Security ahead of a company-wide deadline, and led GitHub Enterprise SOX compliance as project manager and developer.

ResolvedCoverMyMeds · 2025 — now

AI tools that didn’t know how the platform works

Led AI-assisted engineering on the platform team: agent context files across all platform repositories, a shared library of skills, hooks and subagents, packaged as plugins, that encode our runbooks, MCP access to observability data, rollout guardrails with an opt-in usage dashboard, and assistants for onboarding and pre-standup triage.

ResolvedCoverMyMeds · 2022 — now

Hundreds of repositories configured by hand

Brought GitHub organization and repository settings under Terraform and built reusable Azure modules, including Azure Managed Redis with passwordless auth. I run both Terraform Enterprise and HCP Terraform, designed the HCP Terraform access model, and wrote the onboarding guide so teams can self-serve.

100sof repos managed as code
ResolvedCoverMyMeds · 2022 — now

Aging tooling and alerts tied to a retiring chat platform

Owned upgrades and lifecycle for core developer tooling, including GitHub Enterprise Server, centralized audit logging in Splunk, and retired legacy automation tooling. Moved 100+ alerts from Slack to Microsoft Teams before Slack was retired, built Datadog monitoring for pipeline runners, and served as on-call primary for production AKS.

100+alerts migrated
ResolvedCoverMyMeds · 2022 — now

New engineers learning the platform on their own

I mentor new hires and junior SREs, from their first weeks at the company through day-to-day work. I started and ran a weekly hands-on upskilling program, act as a main code reviewer for the team’s infrastructure changes, and introduced team flow practices such as WIP limits.

Resolved84.51° / Kroger · 2019 — 2022

Slow recovery across critical services

Helped found the SRE team and brought in SRE ways of working: SLOs for 10+ critical services, on-call, runbooks and root-cause analysis on major incidents. Led the observability rollout across 100+ microservices, with an Ansible pipeline deploying Prometheus, Thanos and Jaeger alongside Dynatrace.

−40%mean time to recovery
−65%alert noise

Roles

2022 — nowSenior Site Reliability EngineerCoverMyMeds (McKesson) · Remote
2019 — 2022Senior Site Reliability Engineer84.51° (Kroger) · Cincinnati
2018 — 2019Versatilist Engineer84.51° (Kroger) · Cincinnati
2016 — 2018IT Co-op84.51° (Kroger) · Cincinnati
2014 — 2019B.S. Information TechnologyUniversity of Cincinnati

Stack

PLATFORM

  • Terraform · HCP
  • Kubernetes · Helm
  • Azure (AKS)
  • Backstage
  • Docker

DELIVER

  • GitHub Actions
  • Argo CD · Jenkins
  • Python · TypeScript
  • Claude Code · MCP
  • GitHub Enterprise

SECURE

  • SOX / ITGC as code
  • HIPAA · SOC 2
  • GitHub Adv. Security
  • Vault · Key Vault
  • Okta / SSO

OBSERVE

  • Datadog
  • OpenTelemetry
  • Prometheus
  • Grafana
  • Splunk

Service level · working with me

Roles

Senior and staff platform engineering, site reliability engineering, and DevOps / infrastructure roles, plus lead or manager roles for platform and SRE teams.

Open

Location

Based in Chicago. Open to remote (US), hybrid or onsite in Chicago.

Chicago · Remote

Response time

Email is best. I usually reply within a day.

< 24h

Scheduled maintenance

Evenings & weekends

Gym, home-automation projects that are smarter than me, and working through Chicago’s coffee scene one shop at a time.

Recurring