Senior Ruby on Rails + AI Engineer (LLM)

Head Inn is a company focused on transforming enterprise learning through AI-enabled microlearning. They are seeking a Senior AI Systems Engineer to design, build, and scale advanced AI-powered systems, leveraging expertise in Ruby on Rails and large language models to deliver enterprise-grade solutions.

Responsibilities

• Design and implement LLM-powered agentic workflows for real-world tasks.
• Build organization-specific customization layers and AI safety systems.
• Develop voice- and message-based AI learning agents.
• Architect and maintain RAG, vector search, and evaluation pipelines.
• Collaborate with founders, engineers, and clients to shape product direction.

Skills

• 5+ years ML experience (PyTorch, TensorFlow)
• 2+ years with LLMs (Hugging Face, OpenAI, Anthropic)
• Expert Rails engineer (REST APIs, PostgreSQL, ActiveRecord, RSpec)
• Proven track record building and deploying production AI systems
• Familiarity with LangChain / LlamaIndex (or ability to ramp quickly)
• Strong communicator and collaborator, thrives in fast-moving environments

Benefits

• 401k Retirement Plan
• Health, Vision, Dental Insurance
• Founding-level ownership & growth opportunities

Company Overview

• It was founded in undefined, and is headquartered in Antigo, Wisconsin, with a workforce of 2-10 employees. Its website is .