Apprentice, DevOps and IT

Purchasing Platform•Chicago, IL

2d•$30 - $35•Hybrid

About The Position

Weâre transforming property tech! Purchasing Platform Inc. is a next generation marketplace serving the property management sector. Leveraging our market knowledge and tech savvy, we revolutionize the procurement of products and services across the property management sector. By centralizing procurement, our software brings stronger corporate controls and greater spend visibility to portfolio operators of all sizes. 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 â not just ticket-filing. We are not looking for someone who will maintain the status quo. We want someone who is excited to build â 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.

Requirements

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 â you follow through without needing to be chased

Responsibilities

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

Benefits

Competitive hourly pay â this is a paid apprenticeship
Mentorship from senior engineers with real-world startup experience
Hands-on work from day one â no busy-work or coffee runs
Clear milestones and a defined path to a full-time DevOps/SRE role
Exposure to the full tech stack of a growing product company
Health & Wellness: Choose from a variety of health plans tailored to meet your needs. Plus, enjoy a $75/month wellness perk to support your fitness and mental health.
Financial Security: Plan for the future with our 401(k) plan, featuring a company match. We also provide a $75/month remote work expense reimbursement to cover your cell phone or internet costs.
Work-Life Balance: With a minimum of 30 days of paid time off each year, including PTO, holidays, and a winter break, you'll have the time you need to relax and recharge.
Parental Leave: We support new parents with 6 weeks of paid leave, ensuring you have the time to bond with your little one.
Hybrid Work Model: Our team enjoys the flexibility of a hybrid work model. Join us in-office each Tuesday for our All Hands meeting and collaboration sessions. On other days, choose where you work best, whether from home or our office. We also offer a commuter expense reimbursement perk to make your in-office days easier.