Senior Director, Training & Learning Operations

Global Sports Jobs Limited; Los Angeles (CA); Hybrid; USD 210,000 - 260,000; Full time

Benefits offered by this job

Discretionary bonus

Medical insurance coverage

Paid vacation and leave

Commuter benefits

Job summary

Creative Artists Agency (CAA) in Los Angeles seeks a Senior Director of Training & Learning Operations to design and globally execute a comprehensive training strategy that aligns with talent development and corporate culture. You will partner with senior leaders, manage Workday Learning and external vendors, and lead a small team to scale impactful programs across a diverse, global workforce.

The role emphasizes AI literacy, change management, and measurement through leadership dashboards, with

Qualifications

• Bachelor's degree in a related field required.
• 12+ years in training, learning & development, or organisational effectiveness with 3–5 years in a senior leadership role.
• Proven experience designing and executing global training strategies within a complex, matrixed organisation.
• Experience managing learning operations at scale, including LMS administration and vendor/partner management.
• Background in change management principles and their application to training and organisational initiatives.
• Workday LMS expertise: content management, learner reporting, and system configuration.
• Facilitation excellence with engaging learning experiences for diverse audiences.

Responsibilities

• Design, develop, and execute a global training delivery strategy aligned with organisational priorities and values.
• Partner with senior leaders to plan, implement, and oversee change management aspects of global training initiatives.
• Collaborate to ensure an integrated global training strategy with scalable best practices and SOPs.
• Oversee Workday Learning Management System content, UX, reporting, and administration.
• Lead compliance training, rollout management, escalation handling, and results reporting.
• Maintain knowledge of AI-based learning tools and implement innovative solutions to enhance learning and efficiency.
• Manage external learning partners and vendors to ensure quality and value.
• Oversee LA training facility operations, scheduling, and program delivery.

Skills

Leadership

Change management

LMS administration

Facilitation

Instructional design

AI literacy

Stakeholder management

Data analytics

Education

Bachelor's degree

Master's degree (preferred)

Tools

Workday LMS

Job description

About the Role

The Senior Director, Training & Learning Operations is a key leadership role within CAA's Inclusion, Engagement, and Learning and Development organisation in Human Resources. The role is responsible for the design, development, and global execution of a comprehensive training strategy that supports CAA's talent, business goals, and culture. The postholder brings deep expertise in training and learning operations, instructional design, and organisational effectiveness to build scalable, high-impact training programmes for a diverse, global workforce. The role works in close partnership with the Senior Director, Learning & Development, the Global Head of Inclusion, Engagement & Learning & Development, and colleagues across a global Human Resources function to ensure an integrated and unified approach to global learning and training.

Key Responsibilities

• Design, develop, and execute a forward-looking global training delivery strategy aligned with CAA's organisational priorities and values.
• Partner with senior business leaders and key stakeholders to plan, implement, and oversee change management aspects of global training initiatives, including compliance, AI literacy, and skills-based development programmes.
• Collaborate with the Senior Director, Learning & Development to ensure a fully integrated global training and learning strategy, and establish scalable global training best practices and standard operating procedures.
• Provide strategic and operational oversight of CAA's Workday Learning Management System, including content management, system administration, user experience, and reporting.
• Lead compliance training efforts, including reviewing content, ensuring smooth and timely rollouts, managing escalation processes, and regularly reporting on results.
• Maintain current knowledge of AI-based learning tools, systems, and best practices, and identify and implement innovative solutions that enhance the learner experience and operational efficiency.
• Lead the selection and ongoing relationship management of external learning partners and vendors, ensuring quality, value, and alignment with CAA's training objectives.
• Oversee CAA's Los Angeles training facility, including strategic programming, scheduling, and operational management, ensuring a best-in-class environment for in-person learning, executive programming, and facilitation.
• Develop global and locally customisable templates, tools, and resources, and define and track key metrics and analytics to assess learner participation, programme effectiveness, and training impact, translating data into actionable recommendations and leadership dashboards.
• Build and develop a robust train-the-trainer programme, identifying, certifying, and coaching internal facilitators and training champions across global offices.
• Lead, develop, and inspire a team of two, fostering a culture rooted in trust, inclusion, high performance, and continuous growth, and modelling inclusive leadership practices.

Required Experience & Qualifications

• 12+ years of progressive experience in training, learning & development, or organisational effectiveness, with at least 3–5 years in a senior leadership role.
• Bachelor's degree required.
• Proven experience designing and executing global training strategies within a complex, matrixed organisation.
• Experience managing learning operations at scale, including LMS administration and vendor/partner management.
• Background in change management principles and their application to training and organisational initiatives.
• Workday LMS expertise: demonstrated knowledge of Workday Learning, including content management, learner reporting, and system configuration best practices.
• Facilitation excellence: strong facilitation skills with the ability to design and deliver engaging, impactful learning experiences for diverse audiences at all levels of the organisation.
• Training and instructional design best practices: deep understanding of adult learning principles, instructional design methodologies, and current best practices in blended and digital learning.
• Learning operations expertise: experience leading the operational infrastructure of a training function, including scheduling, vendor management, budget oversight, and programme logistics.
• Communications and change management: skilled communicator with the ability to develop compelling training narratives and manage the people side of change through structured change management frameworks.
• Inclusive leadership and team building: demonstrated ability to create a team environment defined by trust, belonging, psychological safety, and a high-performance culture, leading with empathy and equity in all aspects of people management.
• Relationship building and influence: exceptional interpersonal skills with the ability to build meaningful relationships, earn credibility, and effectively influence colleagues and stakeholders at all levels of the organisation without direct authority.
• AI and emerging learning technologies: current knowledge of AI-powered learning tools, platforms, and best practices, with the ability to evaluate and implement technology that enhances learning at scale.

Preferred Skills

• Master's degree in Organisational Development, Education, Human Resources, or a related field preferred.
• Relevant certifications in facilitation, instructional design, change management (e.g., Prosci, CPTD, ATD), or Workday LMS are a plus.

Workplace

This role is hybrid, based in the Los Angeles office.

Benefits & Perks

• Eligible for a discretionary bonus.
• Company pays 80%–100% of the cost of medical insurance, basic life and AD&D insurance, telemedicine, and employee assistance and mental health counselling (in person, virtually, or through text).
• Paid vacation, holidays, and sick time.
• Paid parental leave and other paid leaves of absence, including NICU leave.
• Bereavement resources and adoption benefits.
• Educational assistance.
• Mental health resources and an employee assistance plan.
• Voluntary benefits available, including dental and vision insurance, a 401K plan, flexible spending accounts (health care and dependent care), a health savings account, and voluntary life and AD&D insurance.
• Commuter benefits.
• Other statutory mandated benefits.

About the Company

Creative Artists Agency (CAA) is the leading entertainment and sports agency, with global expertise in filmed and live entertainment, digital media, publishing, sponsorship sales and endorsements, media finance, consumer investing, fashion, trademark licensing, and philanthropy. Founded in 1975, CAA is headquartered in Los Angeles and has offices in New York, Nashville, Memphis, Chicago, Miami, London, Munich, Geneva, Stockholm, Shanghai, and Beijing, among other locations globally.