Lead AI Engineer / Chicago, IL / Hybrid

Looking for an opportunity where you can influence product strategy, architecture, and the future of AI in healthcare? Healthcare technology division of a public traded company, is seeking a Lead Software Engineer IV to join their growing team. This is a full-time opportunity that can be based remotely anywhere in the United States or hybrid in Chicago, IL. You’ll work with cutting-edge technologies including Python, JavaScript/TypeScript, AWS, event-driven architectures, relational databases, and AI-powered workflows to build next-generation Revenue Cycle Management (RCM) solutions used by thousands of healthcare providers nationwide.

What makes this role stand out is the chance to help build an entirely new AI-enabled platform from the ground up. You’ll serve as a hands-on technical leader on a highly visible initiative that combines healthcare technology, automation, AI agents, and modern software engineering. The team is looking for a product-minded engineer who enjoys solving real business problems, partnering directly with users, influencing technical direction, mentoring engineers, and shipping impactful products. If you’re excited about building AI-powered software in a healthcare environment while maintaining strong work-life flexibility and high ownership, this is an exceptional opportunity.

Required Skills & Experience

• 10+ years of professional software engineering experience
• Experience leading technical direction and mentoring engineering teams
• Strong development skills with Python and/or JavaScript/TypeScript
• Full-stack application development experience
• API design and development experience
• Event-driven architecture experience
• Message queues, event streams, and asynchronous workflow development
• Strong SQL skills
• Database schema design and optimization
• Experience with ORMs
• Cloud platform experience, preferably AWS
• Product-focused engineering mindset
• Strong communication and stakeholder management skills
• Ability to work cross-functionally with technical and non-technical teams
• Experience leveraging AI throughout the software development lifecycle

Desired Skills & Experience

• Experience integrating LLMs and AI agents into production applications
• AI orchestration and human-in-the-loop workflow experience
• Healthcare technology experience
• Revenue Cycle Management (RCM) experience
• Claims processing experience
• Eligibility and denial management workflows
• Accounts Receivable (A/R) workflow experience
• HIPAA-compliant application development
• Startup or high-growth SaaS experience
• Experience building highly scalable distributed systems

What You Will Be Doing Tech Breakdown

• 35% Python Development
• 25% JavaScript / TypeScript Development
• 15% AWS Cloud Infrastructure
• 15% SQL & Database Design (Postgres, MySQL, MSSQL)
• 10% AI / LLM & Agent Orchestration

Daily Responsibilities

• 75% Hands-On Engineering
• 10% Architecture & Technical Leadership
• 15% Team Collaboration, Product Partnership & Mentorship

The Offer

• Bonus eligible
• Employee Stock Purchase Program (ESPP)
• 401(k) with company match and immediate vesting

You Will Receive The Following Benefits

• Medical, Dental, and Vision Insurance
• Flexible Time Off (FTO)
• Wellness Program & Annual Wellness Stipend
• 401(k) Match
• Professional Development Opportunities
• Employee Stock Purchase Program
• Hybrid or Fully Remote Flexibility

Applicants must be currently authorized to work in the United States on a full-time basis now and in the future. Sponsorship is not available for this position.

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Posted By: Zack Shaikh