Head of AI Enablement

Summary

Join RepeatMD, a leading B2B SaaS company in the Aesthetics and Wellness Industry, as we expand into new verticals. This strategic role will lead our AI Enablement roadmap, focusing on improving Client Experience and Product departments through AI integrations and automation. You will leverage AI tools and agents to increase employee productivity, drive down operational costs, and deliver faster, better outcomes. Your goal is to build RepeatMD’s foundation for an AI-enabled future, implementing AI-driven workflows and automation. This position requires 7-10+ years of experience in technology enablement, operations, or business efficiency within fast-growing SaaS organizations. RepeatMD offers a competitive salary, significant equity, performance bonuses, and comprehensive benefits.

Requirements

• 7–10+ years of experience driving technology enablement, operations, or business efficiency, ideally within fast-growing SaaS organizations
• Proven track record selecting, implementing, and optimizing advanced AI tools and agents within CX, Product, and Engineering workflows
• Strong operational mindset and proven ability to translate strategic business goals into practical AI-driven solutions
• Excellent communication skills to effectively align internal stakeholders, manage change, and drive AI adoption at scale

Responsibilities

• Lead RepeatMD’s AI Enablement strategy, prioritizing Client Experience (Support, Onboarding, Client Success), Sales/Marketing, and Product teams to achieve maximum initial impact
• Identify, vet, and implement cutting-edge AI solutions, automation tools, and AI agents within targeted teams
• Own integration, training, documentation, and enablement of AI agents and tools, ensuring rapid adoption and measurable productivity gains
• Deliver measurable results including significant reductions in customer support costs, increased CX team capacity, accelerated product development cycles, and improved client experiences
• Define clear KPIs, track performance closely, and iterate rapidly to continuously improve AI-driven workflows

Benefits

• Competitive salary + significant equity + performance bonus
• Comprehensive benefits (healthcare, dental, vision, 401k, unlimited PTO)
• Significant opportunity for impact—owning AI enablement at a high-growth, innovative SaaS brand
• Collaborative and ambitious leadership team committed to technology-driven excellence