Apprentice, DevOps and IT
We’re 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 — 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.
Key Responsibilities
Infrastructure & Cloud
- 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)
IT Operations
- 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
What You'll Own
- 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
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 We’re Looking For
Experience & Qualifications
- 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
Tools We Use
- 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 You'll Get
- Competitive hourly pay — this is a paid apprenticeship
- Mentorship from senior engineers with real-world startup experience
- Hands-on work from day one — 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
#LI-Remote
#BI-Remote
Join Our Team: Perks, Benefits, and Culture
At Purchasing Platform, we're not just offering a job; we're inviting you to be part of something bigger. Our comprehensive benefits package and vibrant culture are designed to support your health, well-being, and career growth. Here's what full-time team members can look forward to when joining our team:
Competitive Compensation & Benefits
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.
Our Cultural Hub: Located in the heart of downtown Chicago at 444 N Wells St. Ste 502, our office is more than just a workspace—it's a hub where creativity and collaboration thrive.
Our Core Values
Bring Joy: We believe in making every day enjoyable for our team and our customers.
Value People: Every team member is respected, heard, and valued.
Make an Impact: We're driven to make a positive difference in everything we do.
Keep It Simple: Efficiency and clarity guide our processes and decisions.
Always Be Curious: Continuous learning and innovation are at the heart of our culture.
Commitment to Equality
We are proud to provide equal employment opportunities (EEO) to all employees and applicants, regardless of race, color, religion, sex, sexual orientation, gender identity, national origin, age, or disability. We celebrate diversity and are committed to creating an inclusive environment for all.
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