About the Role
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 — not toy projects or sandboxed exercises.
A core part of this role is using AI tools to replace fragile, manual processes with scalable automation — 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.
Apprenticeship Details
Job Title: Software Engineering Apprentice
Type: Part-Time (20 hrs/week)
Location: Hybrid in Chicago, IL (1-2 days in office per week)
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.
What you’ll be doing
- Write clean, well-tested code in Ruby and JavaScript/TypeScript alongside our engineering team
- Build and ship product features end-to-end — 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
- Features shipped per quarter — measured by test coverage and production stability
- Reduction in manual processing time across workflows you automate — tracked against a defined roadmap
- Quality of code contributions: well-documented, reviewed, and built with the next engineer in mind
- Breadth and reliability of integrations built and maintained
Key Responsibilities
Software Development
AI Integration & Automation
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 codebase and stack, have shipped your first pull request to production, and identified at least one automation opportunity to bring to your manager.
By month three, you are contributing independently to feature work in Ruby and JavaScript/TypeScript, have shipped at least one AI-powered integration, and engineering trusts you to own a slice of the product.
By month six, you are being seriously evaluated for a full-time offer. Multiple workflows have been meaningfully automated, your code is stable and well-reviewed, and the team sees you as a reliable contributor across the stack.
What you'll bring to the role
- Working knowledge of Ruby or JavaScript/TypeScript — 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 — you've integrated AI into a project
- Genuine curiosity about applied AI — you follow the space and have opinions about what's useful
- Strong communicator — you can explain what you built, why it matters, and what comes next
- High ownership mindset — you surface issues proactively and follow through without being chased
- Languages: Ruby, JavaScript / TypeScript
- AI APIs & frameworks: Anthropic Claude, OpenAI, LangChain
- Automation & integrations: REST APIs, webhooks, Zapier, Make (Integromat)
- Data: PostgreSQL, Supabase, Redis
- Dev tooling: Git / GitHub, VS Code, CI/CD via GitHub Actions
- Collaboration: Slack, Notion, Linear — you'll be connecting AI to these too
What We’re Looking For
Experience & QualificationsTools We Use
Top Skills
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