Apprentice, Software Engineering

Purchasing Platform•Chicago, IL

4d•$30 - $35•Hybrid

About The Position

We're looking for a Software Engineering Apprentice to help us build, integrate, and ship AI-powered features on top of our existing product. You'll work directly with our engineering team in Ruby and JavaScript/TypeScript, writing real code in our production stack from day one â not toy projects or sandboxed exercises. A core part of this role is using AI tools to replace fragile, manual processes with scalable automation â connecting systems across Sales, Operations, and Product so that our team spends less time on repetitive work and more time on things that matter. We are not looking for someone who will manage the status quo. We want someone who ships, iterates, and actively looks for the next thing to improve. 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

Working knowledge of Ruby or JavaScript/TypeScript â you've built something real with at least one of them
Familiarity with web development fundamentals: REST APIs, databases, version control with Git
Hands-on experience with at least one LLM API or AI framework â you've integrated AI into a project
Genuine curiosity about applied AI â you follow the space and have opinions about what's useful
Strong communicator â you can explain what you built, why it matters, and what comes next
High ownership mindset â you surface issues proactively and follow through without being chased

Responsibilities

Write clean, well-tested code in Ruby and JavaScript/TypeScript alongside our engineering team
Build and ship product features end-to-end â from scoping and implementation through deployment and monitoring
Contribute to code reviews, technical discussions, and engineering best practices
Debug and improve existing systems, reducing technical debt and fragile manual workarounds
Build AI-powered features and workflows using LLM APIs (Anthropic, OpenAI, etc.) in our existing stack
Connect internal and third-party tools via APIs and integrations (CRMs, project trackers, databases)
Partner cross-functionally with Sales, Ops, and Product to identify and automate high-impact manual processes
Document integration patterns, experiments, and results clearly for the wider team

Benefits

Competitive hourly pay â this is a paid apprenticeship
Direct mentorship from engineers working across our full product stack
Real ownership of features and automations that ship to production
A portfolio of shipped code and live integrations you can point to
A defined path to a full-time Software Engineer role
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.