About Collars

Collars is a mobile-first hiring platform built for the skilled trades industry. We connect applicants with employers across the Chicagoland market. We're a small, fast-moving team building modern hiring infrastructure for a sector that's been largely left behind by existing technology.

About the Role

We're looking for a contract AI Automations Engineer to build and scale internal automation workflows across our team. We have specific automations already planned and scoped - your first job is to execute on those. From there, we want someone who will work directly with each department to surface new opportunities and continuously improve how we operate.

This is a purely internal-facing role. You won't be building anything product-facing. You'll work closely with our CTO and small team, so clear communication, planning and ownership matter as much as technical ability.

What You'll Work On

• Build and deploy automation workflows in n8n
• Lead upfront discovery before any build begins: audit existing workflows and produce a structured automation roadmap that gets reviewed and approved
• Develop AI agents using the Claude API to automate repetitive internal tasks
• Integrate with our tool stack: Linear, Notion, Attio, Microsoft 365, and Stripe
• Connect automations to our internal NestJS APIs where needed
• Partner with each department to identify new automation opportunities and optimize existing workflows
• Document everything you build so the team can maintain and extend it without you

What We're Looking For

• Hands-on n8n experience with building complex, multi-step workflows (not just simple templates)
• Experience building with the Claude API or comparable LLM APIs
• Solid understanding of autonomous AI agent patterns
• Comfortable working with REST APIs and webhooks
• Experience integrating tools like Notion, Linear, CRMs, and Microsoft 365
• Able to work independently with minimal oversight
• Familiarity with Model Context Protocol (MCP) and how it connects AI models to external tools and data sources
• Strong written communication and documentation habits

Nice to Have

• Familiarity with NestJS or Node.js
• Prior experience with Attio or similar CRMs
• Background working with early-stage startups

What This Is Not

• This is not a full-time role
• This is not a product or engineering role
• This is not an ML/AI research or model development role

How We Work

Small team, high ownership, direct access to leadership. You won't be navigating bureaucracy or waiting on approvals. We expect clear, proactive communication and work that holds up over time. This engagement is open to contractors based in the Chicagoland area only.

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Interested?

Shoot Daniel a message on LinkedIn. No calls or emails, please.