4th Engineer / Onsite Chicago / Python / Healthcare Startup

A Chicago-based healthcare technology startup is seeking their 4th full-time Senior Software Engineer to help build AI-powered products that improve access to behavioral healthcare. This venture-backed organization is leveraging modern AI technologies, LLMs, and full-stack engineering to solve complex operational challenges within the healthcare system. The position is primarily based in downtown Chicago with flexibility for exceptional candidates willing to spend significant time collaborating with the team in person in River North.

This is a rare opportunity to join an exceptionally small engineering team and influence the company during its earliest stages of growth. The ideal candidate is a hands-on builder who thrives in startup environments, enjoys moving quickly, and wants meaningful ownership over both product and technical decisions. This team likes to have fun, but in this stage they need someone who is willing and able to dedicate 60+ hours a week to being hands-on writing code while contributing to shaping architecture, engineering processes, and the future direction of the platform, working directly alongside company founders. Required Skills & Experience

• 4+ years of professional software engineering experience
• Ability to work 60+ hours per week, including occasional weekends
• Experience in early-stage startups or high-growth environments
• Full-stack development experience
• Strong proficiency with modern web technologies
• Experience building and shipping customer-facing applications
• Demonstrated project ownership from concept to deployment
• Experience collaborating closely with product and business stakeholders
• Strong communication and problem-solving skills
• Ability to work independently in fast-changing environments

Desired Skills & Experience

• Previous Founding Engineer or early engineering hire experience
• Experience with LLMs, AI agents, or generative AI products
• Startup leadership or mentoring experience
• Healthcare or health-tech exposure
• Experience designing scalable systems and technical architecture
• Familiarity with cloud infrastructure and DevOps practices
• Experience leveraging AI-assisted development tools

What You Will Be Doing Tech Breakdown

• 40% Full-Stack Product Development
• 25% AI & LLM Integrations
• 20% Platform & Infrastructure Engineering
• 15% Technical Architecture & System Design

Daily Responsibilities

• Build and launch AI-powered product features
• Partner directly with founders to define product direction
• Design scalable architecture and engineering solutions
• Own features throughout the entire development lifecycle
• Contribute to infrastructure, deployment, and operational excellence
• Help establish engineering best practices as the team grows
• Evaluate and implement emerging AI technologies where appropriate
• 80% Hands-On Development, 5% Team Leadership & Mentorship, 15% Cross-Functional Collaboration

The Offer You will receive the following benefits:

• Competitive base salary
• Bonus eligible
• Equity participation with meaningful ownership potential
• Medical, Dental, and Vision Insurance
• Paid Vacation Time
• Stock Options
• High-impact role within a growing startup
• Direct access to company leadership
• Opportunity to influence technology and engineering culture

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

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