Posted 5 months ago

The Opportunity

We’re hiring a key technical leader to drive AI-enhanced automation and internal tooling across our growing healthcare portfolio.  You will lead our technology initiatives, both independently and in collaboration with our existing on-shore/off-shore development partner.

You’ll be focused on hands-on implementation and innovation within our operating companies, solving real-world operational challenges with modern technology. Your work will be deployed inside:

  • A multi-billion dollar healthcare real estate platform
  • A 10,000+ employee senior care operating company
  • A national behavioral health therapy provider
  • A healthcare billing and RCM firm

This is not a conceptual strategy role — it’s about building and implementing real systems that drive real results. You’ll also contribute to evaluating technical infrastructure and software investments across our portfolio.


What You’ll Do

  • Drive AI-related initiatives, including research, prototyping, implementation planning, project management, and tool evaluation
  • Implement process automation and project/document management solutions across departments (e.g., Monday.com, Power Automate, SharePoint)
  • Work with data teams to define requirements and advise on or create dashboards that support operational visibility and decision-making
  • Help assess software, infrastructure, and automation tools considered by our investment committee
  • Manage external development partners and technical vendors to ensure alignment with project goals, timelines, and quality standards
  • Collaborate with operators, clinicians, and business leaders to align tech with real business outcomes

Long-Term Upside

We also own a nationwide IT infrastructure firm serving hundreds of healthcare facilities — a natural future distribution channel or partner if we expand product offerings.  The solutions we develop in house may grow into standalone SaaS applications or enable us to spin-off into a specialized solution provider.

You may also have opportunities to support our seed and venture investments in emerging healthcare and AI technologies by providing technical insight or helping shape early pilots and partnerships.


Ideal Candidate

  • A high-performing, entrepreneurial technologist with the ambition and capability to take the reins of this initiative — someone who can lead hands-on work today while helping shape the long-term direction of a growing venture
  • Exposure to AI/LLMs and interest in applying them to improve workflows
  • Practical, results-oriented, and hands-on — someone who loves turning ideas into operational systems
  • Entrepreneurial mindset: excited to lead and build, but grounded in real-world delivery
  • Background could include: startup founding or early team roles, consulting in product/tech strategy, or hands-on implementation leadership in healthcare or operations-heavy businesses
VP of Technology-Skokie, IL

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