Director, AI-Driven Executive Experiences

Momentum; Austin (TX); On-site; USD 180,000 - 260,000; Full time

Job summary

Leadout Capital is seeking a Director of Executive Talent Experiences to redefine how senior leaders develop and apply insights within an AI-enabled environment. You will shape strategy, design high-impact experiences, and partner with executives to foster measurable leadership growth and organizational performance.

The role requires strategic thinking, strong stakeholder management, and the ability to operate across design, execution, and measurement in a fast-moving setting.

Qualifications

• Significant experience in executive development, leadership development, talent management, organizational effectiveness, learning experience design, chief-of-staff work, strategy, or a related field.
• Demonstrated ability to design learning and development experiences that result in behavior change and organizational impact, particularly with senior or executive populations.
• Strong understanding of executive leadership, organizational dynamics, talent strategy, and the realities of operating at scale.
• Exceptional executive presence and the ability to build trust and credibility with C-suite and senior leaders.
• Strong chief-of-staff instincts: highly organized, detail-oriented, anticipatory, discreet, pragmatic, and excellent at managing complexity.
• Strong analytical and systems-thinking capabilities; able to synthesize ambiguous inputs, identify patterns, and turn insight into action.
• Experience with executive talent processes such as succession planning, talent reviews, leadership assessments, executive onboarding, or executive coaching.
• Curiosity and demonstrated interest in AI and the future of work and learning, with a willingness to experiment and challenge conventional approaches.
• Excellent written, verbal, facilitation, and stakeholder-management skills.
• Ability to operate comfortably between strategy and execution—zooming out to define the system and zooming in to ensure every detail is right.
• you are equally comfortable in three modes: Strategist — You can see around corners, understand the business, and define what leaders will need next; Designer — You can turn a complex leadership challenge into an experience that changes behavior and creates lasting impact; Operator — You execute with extraordinary precision and care, understand how executives operate, and make complex experiences feel effortless.
• You are intellectually curious, highly discerning, low-ego, and energized by ambiguity; you care deeply about the quality of the experience, but you care even more about whether it actually changes how leaders lead and how organizations perform
• Travel approximately 25%

Responsibilities

• Define and evolve the strategy for executive talent experiences across the company, aligned to business strategy and the capabilities required for the next generation of leaders.
• Design distinctive, high-impact experiences for executives and senior leaders that drive measurable changes in leadership behavior, decision-making, and organizational performance.
• Translate business priorities, leadership challenges, and organizational shifts into targeted development experiences, interventions, and moments that matter.
• Reimagine executive development beyond traditional courses and workshops through experiences, simulations, coaching, peer learning, real-work application, and AI-enabled development.
• Build differentiated experiences for different executive populations, leadership moments, and business contexts.

Job description

Leadout Capital is seeking a Director of Executive Talent Experiences to redefine how senior leaders develop and apply insights within an AI-enabled environment. You will shape strategy, design high-impact experiences, and partner with executives to foster measurable leadership growth and organizational performance.

The role requires strategic thinking, strong stakeholder management, and the ability to operate across design, execution, and measurement in a fast-moving setting.