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through plan selection, coverage questions, and care navigation, yet still rely on spreadsheets, manual workflows, and outdated tools that limit their growth and impact.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 every agency’s close date and full integration on a predictable, repeatable timeline
• Track and report on the outcomes that matter: time to value, number of downline brokers onboarded, revenue generated through the AI platform, and broker/owner NPS

Drive Outcomes with Engineering

• Partner day to day with Engineering and Product on GydeOS integrations, bespoke builds, and automations for our agencies, bringing a clear view of what each agency needs and how fast
• Translate what your team learns in the field into clear technical requirements, so one-off toolkits and automations become durable GydeOS capability

KPIs and Outcomes

Success in this role is measured on the speed, quality, and scalability of the implementation and support motion, including:

• Time to value / time to complete full integration (systems, data, and GydeOS)
• Data migration completeness and accuracy at cutover
• % of eligible brokers (not just agency owners) successfully onboarded and activated on GydeOS
• Configuration quality — commission accuracy in the first payment cycle and hierarchy defect rate
• Revenue generated through AI platform adoption
• Broker and owner satisfaction (NPS)
• Support resolution time and quality, including % resolved without engineering escalation

What you bring and who you are 

• Deep fluency in SQL and Python for data validation, transformation, and one-off scripting — you're not afraid of a messy CSV or a broken upload
• Daily, practical experience with AI coding tools (Claude Code, Codex, or similar) to build and debug independently and move faster than a ticket queue allows
• A track record of building BI/analytics dashboards and reporting from scratch to give stakeholders visibility into a process or system
• Experience building implementation, integration, or onboarding functions (playbooks, SOPs, quality standards, training curricula) from scratch through a period of rapid growth
• Exceptional project management and operational instincts — you keep many cross-functional workstreams moving at once, and naturally think in systems and workflow design, automation, capacity planning, and continuous improvement
• Commercial mindset who indexes on revenue growth and knows how to work with Sales teams to drive towards high-pressure targets and build scrappy solutions when needed
• Cross-functional fluency with Product and Engineering, with the judgment to know when a fix should stay one-off and when it should become permanent product
• Experience owning complex, multi-system integrations end to end — CRM or AMS migrations, data consolidation, vendor cutovers; post-acquisition or multi-entity integration experience is a strong plus
• 8+ years in implementation, integration, onboarding, professional services, technical customer success, or technical product management in B2B SaaS, including building and leading a team — with your hands still genuinely on the keyboard, not purely managing others who are
• Experience as the most senior technical resource on a team — someone both teammates and clients escalate to, not just someone who manages people who do the work (think: solutions engineering lead, forward-deployed engineer, or technical implementation lead)
• Excellent, trust-building people skills; comfort being the face of the company on high-stakes, sensitive agency relationships involving commission and financial data
• Willingness to travel roughly 25% during active implementations

What makes you successful in this role

• You build it yourself before you ask someone else to, and you know the difference between "this needs a bespoke fix now" and "this should become permanent product"
• You think in playbooks and systems, but you're still the first one in when something breaks
• You hold a quality bar under time pressure 
• You're the best technical and client-facing operator on your own team 
• Agency owners trust you fast, even with their most sensitive data and their most sensitive moments
• You're equally comfortable being the safety net for escalations and the person driving the roadmap forward

What we offer

Gyde offers a competitive benefits package to all employees.  

• $215,000 - $245,000 base 
• Flexible (Unlimited) Paid Time Off
• Medical, Dental, and Vision benefits for you and your family
• Retirement Plan (e.g., 401K) 
• Parental Leave