AI Engineer Job at Gyde, Niles, IL

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  • Gyde
  • Niles, IL

Job Description

About Us



  • Insurance brokers sit at the intersection of care, cost, and access — yet remain one of the most underleveraged assets in the $5T healthcare value chain. They guide millions of Americans through plan selection, coverage questions, and care navigation, yet still rely on spreadsheets, manual workflows, and outdated tools that limit their growth and impact.

  • Gyde is reimagining this. We’re building the first AI-native insurance brokerage platform—a system that learns from every client interaction to automate operations, power intelligent voice and chat experiences, and predict the right coverage and products for every individual or business.

  • Our approach combines acquisition and AI: we acquire traditional brokerages and transform them into next-generation, data-driven organizations. Through Gyde’s platform, agencies run more efficiently, serve clients more personally, and scale faster than ever before.

  • Join us if you’re excited to:

    • Redefine how millions of people access and understand their healthcare coverage, by building systems that turn unstructured data, human conversations, and fragmented processes into intelligence.

    • Build AI systems that improve how people access healthcare

    • Design production-grade voice, chat, and predictive models for a highly regulated domain

    • Launch technologies that augment human judgment and make complex decisions transparent and scalable

    • Help reinvent an entire industry from the inside out


  • We’re creating the future of brokerage — where every interaction, insight, and decision is powered by intelligence.

  • Our founding team boasts pedigrees from Oscar, Stripe, and Spark. Lightspeed led Gyde’s Seed financing, with participation from Virtue and Crystal Venture Partners , and angels from Oscar, Uber, and more. 

Role Summary


You will lead the development and delivery of key applications within Gyde’s AI-native brokerage platform—encompassing voice, chat, personalization, and real-time analytics—to drive growth, automation, and insights across acquired agencies. You’ll partner with our COO on AI-driven workflows, and Product on roadmap prioritization.

Key Responsibilities



  • Build AI-driven applications. Develop applications that use LLMs, voice, and chat to automate broker workflows, unlock revenue growth opportunities, and improve member engagement.

  • Ship quality products fast and compliantly. Build tools and infrastructure with a focus on security, reliability, and HIPAA compliance.

  • Integrate with third-party systems. Connect to platforms like AgencyBloc, Sunfire, HealthSherpa, and Ideon to streamline agent and member experiences.

  • Design for scale. Contribute to a modular, multi-tenant architecture that supports tens of agencies and millions of members on our platform, as well as key capabilities that enable agent growth, carrier contracting, commission processing, and reporting.

  • Collaborate across functions. Partner with Ops, Value Creation, and Data teams to translate real-world brokerage problems into elegant, scalable engineering solutions.

What you bring and who you are



  • Strong product sense, fluent in user needs, and an ability to build with empathy for both agents and end consumers (we’ll be in agency offices frequently!).

  • A passion for building on the frontier of AI, and, ideally, experience building AI applications.

  • A high degree of ownership, urgency, and pragmatism. You thrive in ambiguity and take pride in tackling challenging tasks effectively.

  • You will only work with world-class talent, and you are both highly team-oriented and competitive. 

  • Bachelor’s or advanced degree in CS, Engineering, AI/ML, or equivalent.

  • 3+ years of engineering leadership, and 1+ years building AI/ML products at scale

  • Familiarity with health insurance distribution, healthcare, financial services, and HIPAA compliance is preferred but not required.

What we offer


Gyde offers a competitive benefits package to all employees.


  • Top of the market compensation 

  • Flexible (Unlimited) Paid Time Off

  • Remote, or Hybrid Work in Austin or NYC

  • Medical, Dental, and Vision benefits for you and your family

  • Retirement Plan (e.g., 401K) 

  • Parental Leave

Job Tags

Full time, Remote work, Flexible hours,

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