About the Role
We're a fast-moving tech startup looking for a curious, motivated DevOps/IT Apprentice to grow alongside our engineering team. You'll get real exposure to cloud infrastructure, CI/CD pipelines, and internal IT operations — not just ticket-filing.
We are not looking for someone who will maintain the status quo. We want someone who is excited to build — to automate manual processes, improve reliability, and help lay the infrastructure foundation that will support our next phase of growth.
Apprenticeship Details
Job Title: DevOps / IT Apprentice
Type: Part-Time (20 hrs/week)
Location: Hybrid or Remote
Compensation: Paid
Length of Apprenticeship: 6-months
Estimated Start Date: June 1, 2026
This is a paid, part-time role (20 hrs/week) with a genuine path to full-time employment for the right person. You will be expected to roll up your sleeves, ask good questions, and take ownership of your work from day one.
Note: Not open to visa sponsorship at this time.
What you’ll be doing
- Assist with cloud infrastructure setup and monitoring (AWS/GCP/Azure)
- Support CI/CD pipeline maintenance and automation scripts
- Monitor systems and respond to alerts under senior engineer guidance
- Participate in on-call rotations (light exposure, well-supported)
- Help manage internal IT: devices, access, accounts, and onboarding
- Document processes, runbooks, and infrastructure diagrams
- Partner cross-functionally with product and engineering on systems improvements
- Identify manual or fragile workflows and propose automation solutions
- Number of manual processes automated or documented per quarter
- System uptime and incident response time (supported, not solo)
- Quality and completeness of internal IT documentation and runbooks
- On-time delivery of assigned infrastructure tasks
Key Responsibilities
Infrastructure & Cloud
IT Operations
What You'll Own
What Success Looks Like Over the Next 6 Months
Within the first 30 days, you will have a working understanding of our infrastructure, have shadowed key systems, completed your first documented runbook, and identified at least one process that could be automated or improved.
By month three, you are contributing independently to infrastructure tasks, have shipped at least one automation or improvement, and engineering trusts you to own a slice of operations.
By month six, you are being seriously evaluated for a full-time offer. Our internal IT is better documented, key manual workflows are more automated, and you are a reliable partner to the engineering team.
What you'll bring to the role
- Currently studying or recently graduated in CS, IT, or a related field
- Familiarity with Linux/Unix command line basics
- Exposure to at least one cloud platform or containerization (Docker/K8s a plus)
- Some scripting experience (Bash, Python, or similar)
- Reliable, communicative, and genuinely curious about how systems work
- High ownership mindset — you follow through without needing to be chased
- Cloud & Infra: AWS / GCP, Terraform, Docker, Kubernetes
- CI/CD: GitHub Actions, CircleCI
- Monitoring: Datadog, PagerDuty, Grafana
- Collaboration: Slack, Notion, Linear, Jira
- Version control: Git / GitHub
What We’re Looking For
Experience & QualificationsTools We Use
Top Skills
What We Do
Purchasing Platform is a unique B2B marketplace tailored for all sectors of property management. We leverage cutting-edge technology to empower property portfolios, enabling them to manage purchasing activities efficiently across all properties while driving real cost savings from trusted suppliers. Our platform services portfolios across the nation, enhancing operational workflows with features like embedded multi-level workflows, automated expense classification, and our proprietary integration with accounting software systems.
Why Work With Us
Whether it's our employees or customers, we put People first. Our culture is built on transparency, empowerment and accountability. Our platform is designed from the ground up to provide unbeatable value and savings to our customers. The result is the rapid growth we all dream of being a part of. Come join the team!
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Purchasing Platform Offices
Hybrid Workspace
Employees engage in a combination of remote and on-site work.
Our hybrid policy allows employees to work however they work best. Employees are encouraged to work in our Chicago office one day per week.



