Head of AI Deployment

The posting, as Gyde wrote it

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through plan selection, coverage questions, and care navigation, yet still rely on spreadsheets, manual workflows, and outdated tools that limit their growth and impact.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 writin
[…]
ency 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