Head of AI Deployment

Gyde•Austin, TX

3d•$215,000 - $245,000

About The Position

Gyde is building an AI-native insurance brokerage platform that combines acquisitions with technology to modernize brokerage operations, automate workflows, and support intelligent voice, chat, and predictive experiences. The Head of AI Deployment will build and lead the function responsible for integrating acquired agencies and deploying GydeOS, from acquisition close through steady state. The role owns systems and data migration across HR, IT, finance, and operations; CRM and agency management system cutovers; book-of-business ingestion; commission configuration; hierarchy mapping; carrier contracting; and GydeOS deployment, including campaign and AI Skill setup. The position is a hands-on, player-coach role. It will establish repeatable integration playbooks, SOPs, quality gates, training curricula, dashboards, and tooling, while personally leading complex or high-risk implementations and serving as the senior technical escalation point. The Head of AI Deployment will build one-off scripts, data transformations, dashboards, and CRM implementations as needed, and work with Product and Engineering to turn recurring solutions into durable GydeOS capabilities. The role leads a team of AI Deployment Specialists and partners closely with Partner Growth, Product, Engineering, Marketing, and acquired agency leadership. It is accountable for integration speed, quality, broker adoption, support outcomes, and revenue generated through AI platform adoption. The position includes roughly 25% travel during active implementations.

Requirements

Deep fluency in SQL and Python for data validation, transformation, and one-off scripting.
Daily practical experience using AI coding tools such as Claude Code, Codex, or similar to build and debug independently.
Experience building BI/analytics dashboards and reporting from scratch to provide visibility into a process or system.
Experience building implementation, integration, or onboarding functions from scratch, including playbooks, SOPs, quality standards, and training curricula, through a period of rapid growth.
Exceptional project management and operational instincts, including managing concurrent cross-functional workstreams and applying systems and workflow design, automation, capacity planning, and continuous improvement.
Commercial mindset focused on revenue growth, with experience working with Sales teams toward high-pressure targets and building scrappy solutions when needed.
Cross-functional fluency with Product and Engineering, including judgment about when a fix should remain one-off and when it should become permanent product.
Experience owning complex, multi-system integrations end to end, such as CRM or AMS migrations, data consolidation, and vendor cutovers.
At least 8 years of experience in implementation, integration, onboarding, professional services, technical customer success, or technical product management in B2B SaaS, including building and leading a team while remaining hands-on technically.
Experience as the most senior technical resource on a team and as an escalation point for teammates and clients.
Excellent, trust-building people skills and comfort representing the company in high-stakes agency relationships involving commission and financial data.
Willingness to travel roughly 25% during active implementations.

Nice To Haves

Post-acquisition or multi-entity integration experience.

Responsibilities

Own acquired-agency integrations from close to steady state, including systems and data migration, CRM and agency management system cutover, book-of-business ingestion, commissions configuration, hierarchy mapping, carrier contracting, and GydeOS deployment.
Build integration playbooks and SOPs, define quality gates, and run integration readiness and sign-off with Partner Growth and acquired agency leadership.
Coordinate HR, IT, finance, operations, and engineering as the internal project manager for each integration, keeping systems, data, and people on a shared timeline.
Lead systems and workflow design for integrated agencies by mapping current workflows, adapting them to Gyde’s stack, and planning team capacity for new ways of working.
Document and train the team on configuring Gia for agency-specific books, carriers, line-of-business entitlements, and workflows.
Own internal team and external agent/broker training, including customer-service workflows, FAQ pages, training curricula, enablement libraries, email templates, SLAs, webinars, train-the-trainer materials, and downline enablement.
Partner with Product on feature and product rollouts and with Marketing on training agents and brokers on new capabilities.
Drive downline broker onboarding and adoption at scale and continuously improve integration speed, quality, and consistency.
Build agency-specific data transformations, scripts, troubleshooting tools, dashboards, reporting, and CRM implementations; source or implement vendor tools where gaps emerge.
Partner with Product and Engineering to convert recurring one-off fixes into permanent, automated GydeOS capabilities and communicate field learnings as technical requirements.
Personally support the largest, most sensitive, or highest-risk implementations; serve as the senior-most technical escalation point; and set execution standards on flagship implementations.
Hire, onboard, coach, and develop AI Deployment Specialists; establish technical and operational standards; set and monitor SLAs; and own capacity planning, staffing, and resource allocation.
Collaborate with Partner Growth to make time-to-value central to integrations, targeting GydeOS deployment within 3–4 weeks of each agency’s close and predictable full integration timelines.
Track and report time to value, broker onboarding, AI platform revenue, broker and owner NPS, migration accuracy, configuration quality, and support resolution outcomes.
Travel roughly 25% during active implementations.