Founding Engineer / Onsite Chicago / VC-backed Start Up

A venture-backed technology startup in Chicago is seeking a full-time Founding Engineer to help scale an AI-powered platform serving the lower middle market finance sector. This hybrid opportunity is based in River North and combines modern technologies including Python, TypeScript, React, FastAPI, Postgres, cloud infrastructure, and cutting-edge Generative AI solutions.
This is a rare opportunity to join an experienced founder at an early stage and become the technical leader responsible for building both the platform and future engineering organization. The ideal candidate has experience taking products from concept to production, enjoys solving ambiguous problems, and wants the opportunity to shape architecture, engineering culture, and hiring strategy from day one. Candidates seeking ownership, influence, and long-term leadership growth will find exceptional upside in this role. Required Skills & Experience

• Experience founding a startup, serving as a Founding Engineer, CTO, VP Engineering, or leading engineering within an early-stage company
• Proven track record taking products from prototype through production deployment
• Strong software engineering background with modern web technologies
• Experience managing engineers and technical delivery processes
• Hands-on development experience with Python and/or TypeScript
• Experience designing scalable software architecture
• Strong communication skills with both technical and non-technical stakeholders
• Ability to thrive in startup environments with limited structure

Desired Skills & Experience

• Experience with Generative AI, LLMs, RAG systems, or AI agents
• Fintech, accounting technology, or financial services software experience
• Data pipeline and ETL architecture experience
• Experience hiring and scaling engineering teams
• Cloud infrastructure and DevOps expertise
• Startup fundraising or scaling experience

What You Will Be Doing Tech Breakdown

• 35% Backend Engineering (Python / FastAPI)
• 25% Frontend Development (React / TypeScript)
• 20% AI & Data Systems
• 20% Cloud Infrastructure & Architecture

Daily Responsibilities

• 65% Hands On Development
• 15% Management Duties
• 20% Team Collaboration

The Offer You will receive the following benefits:

• Equity participation
• Bonus eligible
• You will receive the following benefits:
• Medical, Dental, and Vision Insurance
• Paid Vacation Time
• Equity / Stock Options
• Leadership Growth Opportunities
• High Visibility Within the Organization

Applicants must be authorized to work in the U.S. on a full-time basis now and in the future.
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