Chief Technology Officer (CTO)

About Gyde

Gyde is the first AI-enable brokerage engineered to provide clients with longitudinal support throughout the healthcare system. Our brokers are truly the entry point to care for their clients and serve as the single source of their client’s comprehensive insurance needs. In doing so, our AI-native platform unlocks unparalleled growth for our brokers, transforming them to market and industry leaders. 

Gyde is assembling the most talented team in the industry in order to bring this vision to life; the founding team already boasts pedigrees from Oscar, Spark, and Stripe. And our seed funding was led by Lightspeed, with participation from Virtue and Crystal Venture Partners. 

Role Summary

As CTO, you will architect and lead the development of our next-generation AI-native brokerage platform, encompassing voice, chat, and hyper-personalization solutions to drive growth for our acquired agencies. Additionally, you will lead the design and development of a robust data infrastructure and integration framework to track the performance of our platform, enabling Gyde to launch new businesses and verticals over time. Your team’s work will be deployed across each acquired agency to:

• Automate and personalize the enrollment and renewal process 

• Drive incremental cross-sell and upsell via predictive insights

• Streamline back-office workflows

• Embed real-time analytics to track outcomes, member preferences, and feedback, and agency performance.

You will recruit, mentor, and manage a market-leading engineering organization, collaborating closely with Corporate Development (during diligence and integration), Operations (to embed AI-driven workflows), and Product (to prioritize feature roadmaps). This role demands a visionary technologist with deep expertise in AI/ML, voice/chat interfaces, data engineering, and API-driven systems integration, preferably hailing from a top-tier tech or research institution.

Key Responsibilities

1. AI Native Platform Architecture & Development

   • Define the end-to-end technical vision for a voice-first and chat-first engagement layer that integrates seamlessly into each agency’s existing CRM, quoting / enrollment platform, and / or dialer. 

   • Lead design and implementation of Gyde’s personalization engine (e.g., recommendation systems for plan matching, renewal nudges) 

   • Oversee speech-to-text and text-to-speech models and conversational AI frameworks.

   • Design and implement core foundational brokerage capabilities including carrier contracting, commission payments, and production reporting
     

2. Data Infrastructure & Analytics

   • Build a centralized data lake (cloud-native: AWS, Azure, or GCP) that ingests and harmonizes data from:

     • Agency management systems (AMS)

     • Quoting / Enrollment Platforms

     • Data submitted by prospective members and existing members 

     • Carrier data sources 

   • Partner with Ops and Data Science to deploy predictive models into production for:

     • Churn prediction (members, insured groups)

     • Next best action algorithms (ancillary products, Medicare Age In prep)

     • Risk stratification for potential clinical outreach

   • Develop a robust security and compliance infrastructure for handling member data
     

3. Systems Integration & Deployment

   • Define an API-first architecture that allows rapid integration into an acquired agency’s tech stack.

   • Partner with Ops to build a post-acquisition integration playbook that’s deployed scalably across many agencies
     

4. Engineering Leadership & Culture

   • Recruit and scale a market-leading engineering organization (backend, frontend, data engineers, ML engineers, DevOps) with a relentless focus on execution, quality, and security.

   • Implement agile processes, code review standards, and CI/CD pipelines to support rapid feature iteration and safe production deployments.

   • Foster a “build-in-public” culture where cross-functional teams (Operations, Corporate Development, Finance) are tightly aligned on product roadmaps, sprint deliverables, and key performance indicators (KPIs).
     

5. Strategic Partnership & Roadmap

   • Work closely with Corporate Development, Operations, and the Leadership team to evaluate target agencies’ tech stacks during due diligence, quantify the integration effort, and estimate the time-to-value for platform rollout.

   • Create a multi-quarter technology road map aligned with business milestones, and partner with leadership to measure progress.

   • Stay abreast of emerging AI innovations and evaluate how they can be incorporated to maintain our technology moat and enable further transformations of the agencies in the future.

Qualifications

1. Education & Experience

• Deep educational background in Computer Science, Engineering, or AI / Machine Learning equivalent from a leading institution

• 10+ years of hands-on engineering leadership experience, ideally:

  • 3+ years building AI/ML-driven products (voice, chat, personalization) in production at scale.

  • 5+ years designing data platforms and ETL pipelines that aggregate multi-source healthcare or insurance data.

  • 3+ years in a senior engineering or architecture role (Director/VP/Head of Technology), leading teams of 20+ engineers.

2. Technical Expertise

• AI/ML & NLP:

  • Experience with transformer-based models and applications for chatbots, voice agents, and personalization.

  • Familiarity with speech recognition and text-to-speech toolkits.

  • Hands-on deployment of ML models in production.

• Data Engineering:

  • Built scalable data lakes and analytics warehouses.

  • Proficient in Python, SQL, and distributed compute frameworks.

  • Expertise in implementing ETL/ELT pipelines.

• Systems Architecture & Integrations:

  • Designed and maintained API-first microservices 

  • Experience integrating with AMS & carrier API ecosystems, ensuring data consistency and secure authentication.

3. Industry Domain Knowledge

• Deep understanding of health insurance distribution models (brokerage economics, commission structures, carrier relationships) preferred but not required.

• Familiarity with regulatory requirements and HIPAA compliance.

• Prior exposure to roll-ups or PE-backed platforms is a plus.

4. Leadership & Cultural Fit

• Proven track record of recruiting and retaining top technical talent in a competitive market.

• Strong communicator and able to translate complex technical concepts into business value for non-technical stakeholders (e.g., CFO, COO, Broker Partners).

• Results-driven mindset with a bias for action: You’ve launched multiple AI-enabled features, measured ROI, and iterated rapidly.

• Entrepreneurial spirit: Comfortable wearing multiple hats, rolling up your sleeves, and navigating ambiguity in a high-velocity roll-up environment.

• Comfort in going on site with agency partners and working directly with the owners to test, iterate, and mature the product