Director, AI Training and Enablement

H.I.G. Capital•Miami, FL

2d•Remote

About The Position

The Director, AI Training & Enablement will lead the design, development, and delivery of AI training and upskilling programs across H.I.G. Capital and its portfolio of companies. Sitting within the Portfolio Operations group, this role supports both firm-side and portfolio company training and upskilling efforts, serving as the central point of coordination between H.I.G., third-party training partners, and portfolio company stakeholders. The Director owns the end-to-end training lifecycle: curriculum strategy, partner-led content development and customization, vendor management, training calendar maintenance, compliance reporting, delivery, and post-program ROI measurement. Most training content is developed in partnership with third-party training providers; this role directs that process, ensures quality and relevance, and supplements with internally developed materials where needed. The AI ecosystem evolves at an extraordinary pace, and this role is responsible for ensuring all training materials are continuously refreshed to reflect the latest platform capabilities, model releases, and best practices. The successful candidate must develop power-user-level fluency across H.I.G.’s AI technology stack (including Anthropic’s Claude, OpenAI’s ChatGPT, and other enterprise platforms) and be capable of delivering training sessions directly when required. This is not a pure project management role. The ideal candidate combines program management discipline with deep technical fluency, a data-driven approach to measuring training ROI, and the ability to engage substantively with both technical and non-technical audiences.

Requirements

Bachelor’s degree in Business, Education, Communications, Information Systems, or a related field; advanced degree or certifications in L&D, instructional design, or technology management are a plus.
5+ years of experience in training program management, learning and development, enablement, or a related function, with demonstrated experience managing third-party training vendors.
Prior experience in private equity, financial services, consulting, or technology companies operating across multiple business units is strongly preferred.
Power-user-level proficiency across enterprise AI platforms (e.g., Claude, ChatGPT, Gemini, Copilot) with comprehensive knowledge of features, configuration options, and integrations.
Must rapidly learn new tools and translate evolving capabilities into actionable training content.
Strong understanding of prompt engineering techniques, AI governance and acceptable use frameworks, and the practical differences between major AI platforms.
Experience with learning management systems (LMS), training analytics, and content authoring tools.
Proven ability to manage complex, multi-stakeholder training programs with competing timelines and diverse audiences.
Track record of measuring training effectiveness and ROI, and using data to continuously improve program outcomes.
Comfortable managing multiple concurrent workstreams across firm-side and portfolio company engagements.
Genuinely curious about AI and emerging technology; actively experiments with new tools and stays current on the rapidly evolving landscape.
Strong executive presence and facilitation skills; comfortable presenting to senior leadership, investment professionals, and portfolio company C-suite executives.
Highly organized with a bias toward action; able to balance strategic curriculum planning with operational demands of calendaring, compliance tracking, and vendor management.
Collaborative and adaptable; builds trust quickly across diverse stakeholder groups and thrives in fast-paced, multi-entity environments.
This is a flexible/remote position; however, candidates should be located within convenient proximity to a major airport given travel requirements.
The role requires approximately 40% travel to H.I.G. offices and portfolio company sites for in-person training delivery, partner coordination, and stakeholder engagement.

Responsibilities

Curriculum Strategy & Content Management: Define and maintain a structured AI upskilling curriculum spanning foundational literacy, platform-specific skills, and advanced use case development, tailored to investment professionals, portfolio company operators, and functional leaders.
Direct the development of training materials (slide decks, hands-on exercises, quick-reference guides, video walkthroughs, assessments) in partnership with third-party training providers, supplementing with internally created content where firm-specific context or rapid turnaround demands it.
Ensure all content is continuously refreshed to keep pace with AI platform evolution, new model releases, and shifting best practices.
Build role-specific learning paths connecting AI capabilities to concrete business outcomes (e.g., deal team due diligence, operational efficiency, finance automation).
Third-Party Partner Coordination & Vendor Management: Serve as primary liaison with external training partners who develop the majority of program content.
Manage scope, timelines, deliverables, and quality.
Evaluate, select, and onboard vendors; negotiate contracts and manage performance against defined KPIs.
Direct partners to customize content to reflect H.I.G.’s specific AI platforms, governance policies, use cases, and organizational context.
Review and approve all partner deliverables for accuracy and relevance.
Training Operations & Direct Delivery: Own the end-to-end training process: maintain firm-wide and portfolio company training calendars, manage participant scheduling and communications, coordinate platform access, and ensure post-session follow-up.
Deliver AI training sessions directly, particularly for firm-specific platforms, workflows, and governance requirements.
Facilitate workshops, office hours, and hands-on labs that build participant confidence.
Maintain power-user-level knowledge of H.I.G.’s enterprise AI tools (Claude Enterprise, ChatGPT Team/Enterprise, ToltIQ, and emerging platforms), including all major features, integrations, and configuration options.
Manage training compliance reporting, tracking completion requirements and ensuring all mandatory programs are delivered on schedule.
Program Measurement, ROI Tracking & Adoption Analytics: Define and own training program KPIs: completion rates, participant satisfaction, knowledge retention, post-training platform adoption, and usage growth metrics.
Build and deliver recurring ROI reporting to H.I.G. leadership, quantifying business impact of upskilling programs (e.g., productivity gains, time savings, workflow adoption rates) across both the firm and portfolio companies.
Use adoption data and participant feedback to identify skill gaps, refine curriculum, and make data-backed recommendations for future training investments.
Change Management & Upskilling Strategy: Partner with H.I.G.’s GenAI Champions network and Strategy & Transformation Operating Partners to embed AI upskilling into broader digital transformation initiatives.
Collaborate with training partners to develop enablement campaigns (newsletters, tip sheets, use case libraries) that reinforce training and sustain adoption momentum between formal sessions.
Identify and cultivate internal AI power users who can serve as peer coaches and adoption accelerators within their teams.