Senior Director, Training & Learning Operations

ROSTR, Inc.; Northern, Los Angeles (KY, CA); Hybrid; USD 227,000 - 260,000; Full time

Job summary

Creative Artists Agency (CAA) seeks a Senior Director, Training & Learning Operations to design, lead, and scale a global training strategy. This leader will oversee LMS (Workday) administration, vendor partnerships, and analytics, while shaping learning programs that support a diverse, global workforce.

Based in Los Angeles with a hybrid schedule, you will partner with senior executives across HR and business units to drive measurable learning outcomes and a culture of continuous development.

Qualifications

• 12+ years of progressive experience in training, learning & development, or organizational effectiveness, with 3–5 years in a senior leadership role.
• Bachelor’s degree required; Master’s degree preferred in a related field.
• Certifications in facilitation, instructional design, change management (e.g., Prosci, CPTD, ATD) or Workday LMS are a plus.
• Proven experience designing and executing global training strategies within a complex, matrixed organization.
• Experience managing learning operations at scale, including LMS administration and vendor/partner management.
• Background in applying change management principles to training and organizational initiatives.

Responsibilities

• Design, develop, and execute a forward-looking global training delivery strategy aligned with priorities and values.
• Partner with senior leaders to plan, implement, and oversee change management for global training initiatives including AI literacy.
• Collaborate with Learning & Development to ensure integrated global strategy across regions.
• Establish scalable global training best practices and standard operating procedures.
• Provide strategic and operational oversight of Workday LMS content management, administration, and reporting.
• Lead vendor/partner management for external learning providers and measure training impact.
• Oversee Los Angeles training facility programming and operations.
• Develop templates, tools, and dashboards to track participation and program effectiveness.
• Build a robust train-the-trainer program and coach internal facilitators.
• Lead a team of two and foster a culture of trust, inclusion, and high performance.

Skills

Workday LMS Expertise

Facilitation Excellence

Training & Instructional Design

Learning Operations

Communications & Change Management

Inclusive Leadership & Team Building

Relationship Building & Influence

AI & Emerging Learning Technologies

Education

Bachelor’s degree

Master’s degree in Organizational Development, Education, Human Resources, or related field (preferred)

Tools

Workday LMS

Job description

Who We Are

Creative Artists Agency (CAA) is the leading entertainment and sports agency, with globalexpertisein filmed and live entertainment, digital media, publishing, sponsorship sales and endorsements, media finance, consumer investing, fashion, trademark licensing, and philanthropy.Distinguished by its culture of collaboration and exceptional client service, CAA’s diverse workforceidentifies, innovates, and amplifies opportunities for the people and organizations that shape culture and inspire the world.The trailblazer of the agency business, CAA was the first to build a sports business, create an investment bank, launch a venture fund, found technology start-up companies, establish a philanthropic arm, build a business in China, and form a brand marketing services division, among other innovations. Named Most Valuable Sports Agency by Forbes for eight consecutive years, CAA represents more than 2,000 of the world’s top athletes in football, baseball, basketball, hockey, soccer, in addition to coaches, on-air broadcasters, and sports personalities and works in the areas of broadcast rights, corporate marketing initiatives, social impact, and sports properties for sales and sponsorshipopportunities.Foundedin 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.

The Role

The Senior Director, Training & Learning Operations will serve as a key leader within CAA’sInclusion, Engagement, and Learning and Developmentorganizationwithin Human Resources, responsible for the design, development, and global execution of a comprehensive training strategy that supports CAA’s talent, business goals, and culture. This individual will bring deepexpertiseintraining andlearning operations, instructional design, and organizational effectiveness to build scalable, high-impact training programs that serve a diverse, global workforce.

This role works in close partnership with the Senior Director, Learning & Development,Global Head of Inclusion, Engagement & Learning & Developmentand across a global Human Resources function,to ensure an integrated and unified approach to global learning and training — one that is grounded in measurable outcomes and a shared commitment to building a global culture of continuous learning.

Responsibilities

Global TrainingDeliveryStrategy

• Design, develop, and execute a forward-looking global trainingdeliverystrategy aligned with CAA’s organizational 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 programs
• Collaborate closely with the Senior Director, Learning & Development to ensure a fully integrated global training and learning strategy that drives consistent, high-quality experiences across all regions
• Establish scalable global training best practices and standard operating procedures that enable consistency and efficiency across markets

Learning Management System (LMS) & Technology

• Provide strategic and operational oversight of CAA’s Workday Learning Management System (LMS), including content management, system administration, user experience, and reporting
• Lead compliance training efforts in close partnership with stakeholders across CAA: lead team to review content, ensure smooth andtimelyrollouts, manage escalation processes, and regularly report on results.
• Maintain current knowledge of AI-based learning tools, systems, and best practices;identifyand 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

Los Angeles Learning Facility

• Oversee CAA’s Los Angelestrainingfacility, including strategic programming, scheduling, and operational management
• Ensure the facility serves as a best-in-class environment forinnovative and engagingin-person learning experiences, executive programming, and facilitation

Tools,Measurement & Analytics

• Develop /identifyglobal and locally customizable templates, tools, and resources to drive consistency and cohesion in learning practices and processes
• Define and track key metrics and analytics to assess learner participation, program effectiveness, and overall training impact across the organization
• Translate data insights into actionable recommendations that continuously improve training quality and business outcomes
• Develop and present regular reporting and dashboards for senior leadership

Train-the-Trainer & Capability Building

• Build and develop a robust train-the-trainer program that enables global consistency in training practices, facilitation standards, and program execution
• Identify, certify, and coach internal facilitators and training champions across global offices

Team Leadership

• Lead, develop, and inspire a team of 2, including a Learning Solutions Manager and an LMS Administrator
• Foster a team culture rooted in trust, inclusion, high performance, and continuous growth
• Model inclusive leadership practices and create an environment where every team member can thrive and deliver their best work

Qualifications

• 12+ years of progressive experience in training, learning & development, or organizational effectiveness, with at least 3–5 years in a senior leadership role
• Bachelor’s degreerequired;Master’s degree in Organizational 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
• Proven experience designing and executing global training strategies within a complex, matrixed organization
• Experience managing learning operations at scale, including LMS administration and vendor/partner management
• Background in change management principles and their application to training and organizational initiatives

Skills & Competencies

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 organization.

Training & 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 programlogistics.

Communications & 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 & Team Building

Demonstrated ability to create a team environment defined by trust, belonging, psychological safety, and a high-performance culture. Leads with empathy and equity in all aspects ofpeoplemanagement.

Relationship Building & Influence

Exceptional interpersonal skills with the ability to build meaningful relationships, earn credibility, and effectively influence colleagues and stakeholders at all levels of the organization — without direct authority.

AI & Emerging Learning Technologies

Current knowledge of AI-powered learning tools, platforms, and best practices; ability to evaluate and implement technology that enhances learning at scale.

Location

This role ishybrid,based in ourLos Angeles office.

Compensation

The annual base salary for this position is in the range of $227,000 - $260,000 inLos Angeles, CA. This position is also eligible for benefits and a discretionary bonus.Ultimately, thesalary may vary based upon, but not limited to, relevant experience, time in the role, business sector, and geographic location, among other criteria.