[Hiring] Director, AI Training and Enablement @H.I.G. Capital

Role Description

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. 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

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 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.

Qualifications

• 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.
• 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.

Requirements

• 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.
• Manage training compliance reporting, tracking completion requirements and ensuring all mandatory programs are delivered on schedule.
• 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.
• Use adoption data and participant feedback to identify skill gaps, refine curriculum, and make data-backed recommendations for future training investments.
• 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 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.

Benefits

• 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.