Head of Learning and Leadership Development, Director

Guggenheim Investments•Stamford, CT

4d•Onsite

About The Position

Guggenheim Investments is seeking a Learning and Leadership Development leader to build employee, manager, and leadership capabilities and foster a continuous learning culture. This builder-and-operator role sets the enterprise learning strategy, designs development curricula and programs, and runs them across the employee lifecycle, from new-manager readiness to senior and executive leadership development. The role also leads future-ready skills initiatives, including AI fluency and adoption, reskilling and upskilling, and function-specific and technical learning for investment and corporate professionals. The role owns all four pillars of the Learning function and is accountable for capability outcomes rather than activity measures. Success is reflected in improved management, leadership readiness, and employee skills aligned to future business needs. The position is based in the Stamford, Connecticut office, with frequent travel to the New York City office. The role sets a multi-year learning roadmap; partners with business leaders, HR Business Partners, and functional heads to identify and address capability gaps; owns manager and leadership development; and works closely with the Head of Talent Management & Culture to align development with performance, talent review, advancement, and succession frameworks. It also owns the learning platform, content portfolio, vendor and coaching-provider relationships, learning budget, and measurement approach, and builds and develops the Learning & Leadership Development team. Inclusive leadership practices and equitable access to development are to be embedded across the function’s four pillars.

Requirements

At least 10 years of experience in learning and development, leadership development, organizational development, or talent, including direct ownership of enterprise learning strategy or a leadership development portfolio.
Demonstrated experience designing and launching manager and leadership development programs end to end.
Track record designing or running executive development and coaching programs, with credibility working directly with senior leaders.
Experience conducting learning needs assessments and building curricula tied to capability gaps and business outcomes.
Ability to define and report learning outcome metrics and use data to change programs.
Working knowledge of learning platforms and digital content, and a practical perspective on how AI changes what and how people need to learn.
Exceptional facilitation, influence, and executive communication skills.
Bachelor’s degree or equivalent experience.
Must be authorized to work in the United States without current or future visa sponsorship or transfer.

Nice To Haves

Financial services, asset management, or other regulated-industry experience, including developing investment or other highly technical professionals.
Experience establishing a learning function or materially rebuilding one.
Experience leading an enterprise AI fluency, digital skills, or reskilling program.
People management experience.
Coaching or assessment certification (such as an ICF credential, Hogan, MBTI, or 360 instruments) or relevant L&D credentials (such as ATD CPTD).

Responsibilities

Set a multi-year learning and leadership development roadmap based on needs assessment and business priorities.
Partner with business leaders, HR Business Partners, and functional heads to diagnose capability gaps and create targeted development.
Design and run the manager development pathway, including new-manager readiness, core curricula, coaching and feedback skills, and performance and talent management capability.
Build and govern the leadership capability framework and use it to guide senior leader development, executive development and coaching, and support during leadership transitions.
Partner with the Head of Talent Management & Culture to align learning with performance, talent review, advancement, and succession frameworks, and to develop the future leadership pipeline.
Lead AI fluency and adoption learning in partnership with Technology, Risk, and Compliance, alongside reskilling and upskilling programs.
Own the learning platform, content portfolio, vendor and coaching-provider relationships, and learning budget; make build-versus-buy decisions.
Define and use learning outcome metrics, including manager effectiveness, leadership readiness, skill acquisition, and internal mobility, to improve programs.
Build, lead, and develop the Learning & Leadership Development team.
Embed inclusive leadership practices and equitable access to development across the four learning pillars.
Own enterprise learning strategy, the skills and capability agenda, structured learning needs assessments, enterprise curriculum, platform, and content portfolio; determine what to build, buy, or retire.
Prepare employees for management and improve manager effectiveness; develop coaching, feedback, performance management, and talent management capabilities in partnership with Talent Management.
Own the leadership capability framework, senior leader development, executive development and coaching, support for critical leadership transitions, and leadership pipeline development with Talent Management.
Build function-specific, technical, and professional skills in partnership with business and functional leaders; own AI fluency and adoption, reskilling and upskilling, and career development resources.