Remote Python Developer Apprenticeship Jobs in Vernon Hills, IL

Overview
Ontrac Solutions is seeking a high-aptitude Production Engineer (IC2) to support a large-scale enterprise OS modernization and infrastructure hardening program for one of our enterprise clients. This role is built for an engineer with real software engineering foundations specifically Python who has since moved into infrastructure and is comfortable working across OS modernizations (RHEL7 EL8/EL9), packaging migrations (Chef CINC), and CI/CD hardening, while simultaneously executing hands-on runbooks, automation, and service onboarding.

This is a genuine hybrid role: roughly half build Python tooling, RPM packaging, pipeline and rollback work and half operate runbooks, service onboarding, and Tier-2 break/fix. You will work directly with the client's SRE organization, internal engineering teams, and customer stakeholders from initial definition through final delivery. Candidates who are pure application developers with no Linux fleet exposure, and candidates who are pure operations with no real software engineering behind them, will not clear screening.

What your application must clearly show
We screen against the requirements below exactly as written your resume should make these easy to find. Specifics matter more than vocabulary: a resume that restates this posting's terminology without the detail below will not advance.

• Python you actually wrote, described as software, not as a skills keyword. Name the project, what it did, who depended on it, and how it was tested and shipped. "Python (scripting)" in a skills list will not clear this bar. A GitHub, GitLab, or public repo link is strongly preferred we look at code.
• RPM packaging you personally did. Name the .spec files you authored or maintained, how you handled dependencies and versioning, your build tooling (rpmbuild, mock, Koji, or an internal builder), roughly how many packages you owned, and where they were published.
• A real OS migration you worked on with version numbers and what actually broke. System Python 23, OpenSSL and crypto-policy changes, systemd unit differences, deprecated or renamed packages. We are more interested in the failure modes you hit than in the name of the program.
• Configuration management you have run in production Chef (cookbooks, recipes, Ohai, Test Kitchen/InSpec), CINC, Puppet, Ansible, or Salt. Say which resources you wrote and how you tested convergence.
• Monitoring and logging work you executed. Name the stack, what you onboarded to it, and what you actually instrumented metrics, dashboards, alert rules, log pipelines not just the product name.
• Tier-2 or on-call experience: the rotation you carried, the scale of the fleet behind it, and one incident you personally drove to resolution.
• CI/CD pipelines you built or hardened, including how rollout and rollback were handled when a change went wrong.
• Your certifications, named, with dates and credential IDs or verification links we verify certifications.

Shortly after you apply you will receive a short role-specific questionnaire completing it promptly is the fastest way to move into screening.

Required Qualifications:

• Software engineering foundation: 3+ years of professional software engineering experience, with strong hands-on Python. You have written and maintained code other engineers depended on modules, packaging, tests, code review, and version control, not just single-file scripts.
• Enterprise OS modernization: Hands-on experience with enterprise Linux at fleet scale and with large-scale OS upgrade programs RHEL7 EL8/EL9 or an equivalent major-version migration you executed rather than observed.
• Packaging migrations: Experience building RPM packages to replace legacy configuration, and with large-scale packaging or configuration-management migrations such as Chef CINC.
• Independent bug ownership: Able to triage, own, and resolve bugs end to end without hand-holding reproduce, isolate, fix, test, and ship.
• CI/CD and release safety: Ability to harden CI/CD pipelines, observability frameworks, and rollout/rollback mechanisms specifically tailored for legacy-to-modern infrastructure transitions.
• Tier-2 operational support: Willingness and experience to partner closely with an SRE team providing "follow-the-sun" tier-2 support, including hands-on incident response and break/fix operations on existing platforms.
• Service onboarding: Experience onboarding services to newly established monitoring and logging stacks.
• Automation and documentation: A demonstrated habit of automating repetitive operations and documenting technical procedures for others to run.
• Location and work authorization: Must be located in the United States and authorized to work in the US.

Preferred Qualifications:

• Proven experience planning and executing logging and monitoring tool rollouts end to end not only operating a stack someone else stood up.
• Experience supporting a team through cloud cutovers and component migrations to cloud environments.
• Perl scripting experience legacy tooling in this environment is Perl, and the ability to read and safely modify it is a real advantage.
• Hands-on exposure to modern observability tooling Chronosphere, Prometheus, or Grafana and to Splunk integrations.
• Provisioning and image work: Kickstart/PXE, golden images, or repository and mirror management.

Key Responsibilities OS Modernization & Packaging:

• Drive the technical transition of legacy systems to modern enterprise Linux environments, including RHEL7 EL8/EL9 upgrade paths.
• Build and maintain RPM packages to replace legacy configuration, and carry the packaging migration from Chef to CINC.
• Develop and execute automated runbooks that make the migration repeatable rather than manual.
• Triage, own, and resolve migration bugs independently, from first report through verified fix.

Key Responsibilities Observability & Monitoring Transition:

• Transition monitoring infrastructure to a modern stack Chronosphere, Prometheus, and Grafana and manage Splunk integrations.
• Onboard services to the newly established monitoring and logging stacks, including metrics, dashboards, and alert rules.
• Harden observability frameworks alongside the pipelines they instrument, so regressions surface before users find them.

Key Responsibilities CI/CD, Rollout & Rollback:

• Harden CI/CD pipelines for legacy-to-modern infrastructure transitions, including build, test, and package promotion stages.
• Design and maintain rollout and rollback mechanisms that make large-fleet changes reversible.
• Automate repetitive operational work and replace manual runbook steps with tested, reviewed code.

Key Responsibilities Tier-2 Operations & Migration Support:

• Provide Tier-2 operational support and incident response under a follow-the-sun model, in close partnership with the client's SRE team.
• Perform hands-on break/fix operations on existing platforms while the modernization proceeds in parallel.
• Assist application developers with architectural support and troubleshooting during cloud migration phases.
• Author and maintain technical documentation runbooks, migration procedures, and package and pipeline ownership notes.

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