V
AI Engineer — First Technical Hire
Valentina Cruz
Full-time · Mid-level · Chicago
About the role
I want to be upfront with you about where we are, because you deserve that before you read a job description. I'm a solo founder. I have a working product — a procurement intelligence tool that uses LLMs to extract structured data from supplier contracts and match it against market benchmarks. I have six paying customers and $180,000 in ARR. I raised a $600,000 pre-seed round in January and have 16 months of runway. I do not have a co-founder. I do not have another engineer. I have been building everything myself, and I have reached the point where the most important thing I can do for this company is hire someone who can take ownership of the technical side while I focus on customers and distribution. The technical work is real and it is not glamorous. It involves improving a RAG pipeline that I built in three weeks and that works well enough for six customers but will not scale to sixty. It involves adding evaluation tooling so that changes can be measured rather than guessed. It involves making architectural decisions that I do not always have the bandwidth to make carefully. If you have ever wanted to be the first engineer at an early company where your decisions actually matter, and you are comfortable with the uncertainty that comes with that, I would genuinely like to hear from you.
Responsibilities
- Own the technical architecture of the product — document what exists, identify the highest-risk gaps, and fix them in priority order
- Rebuild the RAG pipeline to support ten times the current document volume without proportional cost increase
- Build an evaluation framework that makes it possible to measure the effect of every prompt or pipeline change
- Set up basic monitoring so we know when something breaks before a customer tells us
- Work directly with me on customer feedback triage — you will hear directly what's working and what isn't
Requirements
- 3+ years of software engineering with at least 1 year of production LLM or AI system experience
- Python — clean code you're comfortable having a customer's data pass through
- LangChain or equivalent RAG framework experience in a real product, not just a prototype
- OpenAI API hands-on: function calling, structured outputs, context management, cost optimisation
- SQL for the product database — you'll need to understand how extracted data is stored and queried
- Comfort making decisions without full information and communicating clearly when you're uncertain
Benefits
- 0.8% – 1.2% equity on a standard 4-year vest — negotiated based on experience
- Full remote, async-friendly, no imposed process
- $95,000 – $115,000 base salary
- You will be the technical decision-maker — the architecture is yours to shape
- Direct line to customers from day one
Job Type
Full-time
Level
Mid-level
Language
English
Salary Range
$95,000 – $115,000
AI Expertise
NLP & Prompt Engineering
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