Head of AI Deployment

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through plan selection, coverage questions, and care navigation, yet still rely on spreadsheets, manual workflows, and outdated tools that limit their growth and impact.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, Vista Equity Partners, and Alpine. Lightspeed led Gyde’s $60M financing, with participation from Optum Ventures , Crystal Venture Partners , Virtue , MVP Ventures , and multiple endowment funds, among others. Hear why on LSVP Investment Memo .

Role Summary

We’re looking for a technical builder to be Gyde’s Head of AI Deployment and the project manager of every agency integration. You’ll own it end to end, from day-one systems and data migration across HR, IT, finance, and operations through GydeOS deployment and full downline broker activation. There’s a real function to build here: integration playbooks, quality gates, training curricula, dashboards, and the one-off tooling. You’re the person who leads the building of all of it, pulling in your team where it makes sense, and partnering with Product & Engineering when something calls for a more durable, platform-level solution.

Building the integration engine is the primary part of the job. Every acquisition arrives with its own CRM, agency management system, commission and carrier data, contracting setup, and back-office tools, and you own moving all of it onto Gyde’s stack — the SOPs, playbooks, sequencing, and reporting that make integration repeatable and make integration health visible across the portfolio. This is also a build-first role: you're comfortable writing a one-off script to fix a broken data feed, standing up a dashboard so an agency owner can see what clean and aggregated data looks like, or wiring an implementation together with AI coding tools. You know the difference between a problem that needs a bespoke fix today and one that should become a permanent product, and you inform that product roadmap by partnering closely with Product & Engineering to convert the former into the latter over time.

Once that engine exists, you're also its player-coach: the most technically capable and trusted person on the team, not just its manager. You’re not afraid to jump-in to support the largest downlines, the most complicated implementations, the accounts where an error shows up in someone's commission check. And, naturally, you're the person who steps in to diffuse an issue before it escalates.

You'll partner closely with our Head of Partner Growth, who owns the agency relationships, and with Product & Engineering, who build the technology that streamlines integration and GydeOS onboarding. You sit at the intersection of the two: commercially minded enough to push every agency onto GydeOS as fast as possible, and technical enough to work hand in hand with our engineers.

Key Responsibilities

Own End-to-End Integration

Own the end-to-end integration of every acquired agency, from close to steady state — systems and data migration, CRM and agency management system cutover, book-of-business ingestion, commissions configuration, hierarchy mapping, carrier contracting, and GydeOS deployment, including campaign/AI Skill setup

Build the integration playbook and SOPs, define quality gates for each workstream, and run integration readiness and sign-off with Partner Growth and the acquired agency’s leadership

Act as the internal PM for every integration, coordinating HR, IT, finance, operations, and engineering so an agency’s systems, data, and people land on Gyde’s stack on one timeline

Lead systems and workflow design for each integrated agency: map current-state workflows, optimize them for Gyde’s stack, and plan team capacity around the new way of working

Document and train the team on how to configure Gia (our AI agent) to each agency's specific book, carriers, line-of-business entitlements, and workflows

Own internal team training and external agent/broker training, including continuing to build out customer service workflows and FAQ pages (via Looms, Arcade walkthroughs, etc.) and the broader training curriculum and enablement library — email templates, SLAs, recurring webinars, and train-the-trainer materials for downline enablement waves

Partner most closely with Product on new feature and product rollouts, and with Marketing, to train external agents and brokers on new capabilities as they ship

Drive downline broker onboarding and adoption at scale, not just the agency owner relationship

Continuously improve integration speed, quality, and consistency

Build the Technical Toolkit

Build one-off data transformations, scripts, and troubleshooting tools to solve agency-specific problems — using AI coding tools as a daily part of your workflow

Build dashboards and reporting that make onboarding health visible — for a single agency and across the entire portfolio — so gaps get caught before they become escalations

Stand up one-off CRM implementations for agencies outside our supported connector set, and source or implement supporting vendor tools (commissions, contracting, licensing, ticketing, etc.) as gaps emerge

Partner with Product & Engineering to convert recurring one-off fixes into permanent, automated GydeOS capability

Consummate “Player-Coach”

Jump in to support implementation for the largest, most sensitive, or highest-risk agency acquisitions — the accounts where technical complexity, politics, or dollar exposure are too high to hand to a specialist

Serve as the senior-most escalation point for technical issues — the person specialists and agency owners turn to when something breaks

Set the standard of execution personally on flagship implementations before codifying the approach into the team's playbook

Build & Lead the AI Deployment Team

Hire, onboard, coach, and develop a high-performing team of AI Deployment Specialists who own GydeOS onboarding, training, ongoing support, integrations, and bespoke builds for our agencies

Set and hold the technical and operational bar the team is measured against — you can do the hardest version of anyone's job on the team

Set and monitor SLAs for the team, and coach specialists to consistently meet them

Own capacity planning, staffing, and resource allocation across concurrent implementations

Drive Outcomes with Partner Growth

Work in close collaboration with Partner Growth to make time-to-value the central metric of every integration — your goal is to develop an integration playbook that completes GydeOS deployment within 3-4 weeks of eve