Head of Learning and Leadership Development, Director

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Position Summary

Guggenheim Investments is seeking a Learning and Leadership Development leader to build the skills, leadership capabilities and continuous learning culture that employees, managers and leaders need to perform at their best today and to prepare for the future.

This is a builder-and-operator role. The successful candidate will set the enterprise learning strategy, design the curricula and development programs, and run them — from the first day a new manager steps into the role through the development of the firm’s senior and executive leaders. They will also lead the firm’s work on future-ready skills, including AI fluency and adoption, reskilling and upskilling, and the function-specific and technical learning that investment and corporate professionals need to stay at the front of their fields.

The role owns all four pillars of the Learning function. It is accountable for capability outcomes, not learning activity: courses delivered and hours completed are inputs. The test of this role is whether managers manage better, leaders are ready when the firm needs them, and employees build the skills the business will depend on. This role will be based in either Stamford, CT or New York City, full-time.

Responsibilities

Key Responsibilities:

- Set the multi-year learning and leadership development roadmap, grounded in a needs assessment and sequenced against business priorities.
- Partner with business leaders, HR Business Partners and functional heads to diagnose capability gaps and translate them into targeted development.
- Design and run the manager development pathway, from new manager readiness through the core curriculum, coaching and feedback skills, and performance and talent management capability.
- Build and govern the leadership capability framework, and use it to anchor senior leader development, the executive development and coaching program, and support through leadership transitions.
- Partner closely with the Head of Talent Management & Culture so that learning programs build the capabilities that performance, talent review, advancement and succession frameworks require, and so that the future leadership pipeline is developed, not just identified.
- Lead the firm’s AI fluency and adoption learning agenda in partnership with Technology, Risk and Compliance, alongside wider reskilling and upskilling programs.
- Own the learning platform, content portfolio, vendor and coaching-provider relationships, and the learning budget; make disciplined build-versus-buy decisions.
- Build the measurement layer for learning: define outcome metrics (manager effectiveness, leadership readiness, skill acquisition, internal mobility) rather than relying on participation and completion counts.
- Build, lead and develop the Learning & Leadership Development team.
- Embed inclusive leadership practices and equitable access to development across all four pillars (listed below).

Enterprise Learning

Own the enterprise learning strategy and the skills and capability development agenda that flows from it. Run a structured learning needs assessment with the businesses, build and maintain the enterprise learning curriculum, and own the learning platform and content portfolio — what is built in-house, what is bought, and what is retired.

Manager Development

Prepare people for management and make them effective once they are in it. Own new manager readiness and the core manager curriculum; build coaching and feedback skills; develop managers’ capability to run performance and talent management processes well, in partnership with the Talent Management function that owns those frameworks; and measure manager effectiveness so the firm can see whether development is changing how people are managed.

Leadership Development

Define what leadership means at Guggenheim Investments and develop it deliberately. Own the leadership capability framework, senior leader development, and the executive development and coaching program; support leaders through critical leadership transitions; and build the future leadership pipeline in partnership with Talent Management’s talent review and succession work.

Professional & Functional Development

Build the professional and technical skills that the firm’s functions depend on. Own function-specific learning in partnership with business and functional leaders, technical and professional skills development, the firm’s AI fluency and adoption program, reskilling and upskilling, and the career development resources employees use to plan and build toward their next role.

Qualifications

Basic Qualifications:

- 10+ years 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, and credibility working directly with senior leaders.
- Experience conducting learning needs assessments and building curricula tied to identified capability gaps and business outcomes.
- Measurement discipline: able to define and report learning outcome metrics and use the data to change programs.
- Working knowledge of learning platforms and digital content, and a practical point of view on how AI changes both what people need to learn and how they learn it.
- Exceptional facilitation, influence and executive communication skills.
- Bachelor’s degree or equivalent experience.

Preferred Qualifications

- Financial services, asset management or other regulated-industry experience, including developing investment or other highly technical professionals.
- Experience standing up 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 (e.g., ICF credential, Hogan, MBTI, 360 instruments) or relevant L&D credentials (e.g., ATD CPTD).

We are not seeking agency assistance with this role.

We are unable to consider candidates who require current or future visa sponsorship for employment in the United States.  Candidates must be authorized to work in the US without current or future visa sponsorship or transfer.

The benefits offered for this position:

- 401k with matching contribution
- Healthcare and wellbeing programs
- Paid leave
- Learning and development opportunities
- Family and caregiving support
- Employee assistance program

Salary Range

Annual base salary between
$200,000.00-$225,000.00

The base salary range represents the low and high end of the anticipated base salary range for this position. Actual base salaries may vary depending on factors such as location and experience. The range listed reflects base salary only, and the total compensation package may include other components such as incentive compensation.