Director, Digital Workplace Training

Digital Workplace is a core function within OCEO focused on the systems, norms, and operating habits that enable modern execution in a distributed organization. The team is responsible for turning collaboration platforms and productivity tools into a connected digital workplace that supports clarity, transparency, and speed at scale. By establishing shared standards for how information is organized, how work is coordinated, and how leaders and teams collaborate day to day, Digital Workplace reduces friction, improves execution quality, and helps the organization operate as One College Board, regardless of location. 

About the Opportunity 

As Director, Digital Workplace Training, you will build the enterprise capability and confidence required for effective, consistent use of College Board's digital workplace. In a distributed organization with shared tools and ambitious execution goals, productivity depends not just on access to technology but on whether leaders and staff understand how to use those tools in aligned, purposeful ways. This role exists to build that fluency at scale. 

Reporting to the Senior Director, Digital Workplace within the Office of the CEO, you will design and deliver enterprise learning, onboarding, and enablement that reinforce intended usage patterns and support consistent ways of working across the organization. You will translate digital workplace strategy, standards, and workflows into clear, practical learning experiences that help leaders, staff, and their support teams work with greater clarity, speed, and confidence. 

Our ideal candidate understands that effective enterprise training is not about content volume or one-time sessions. It is about behavior change, reinforcement, and confidence over time. You bring strong judgment, a learner-centered mindset, and the ability to design enablement that actually sticks in complex organizational environments. 

In this role, you will 

Enterprise Digital Workplace Learning Strategy (30%) 

• Define the enterprise approach to digital workplace learning, aligned to priority workflows, standards, and execution expectations. 

• Establish required learning pathways for key roles, including leaders, managers, staff, Executive Assistants, and Special Assistants. 

• Ensure learning priorities are driven by enterprise execution needs and adoption gaps, not just tool releases. 

Learning Design and Scalable Enablement (25%) 

• Design and deliver practical, role-specific learning experiences that build confidence and consistency in using enterprise digital tools. 

• Develop scalable learning assets (playbooks, guides, templates, and job aids) that reinforce intended usage patterns and shared ways of working. 

• Ensure learning emphasizes real workflows and behaviors rather than abstract tool functionality. 

Enterprise Onboarding and Change Enablement (20%) 

• Integrate digital workplace learning into enterprise and divisional onboarding experiences. 

• Partner with the Digital Workplace Product Manager and Technology during major tool, platform, or workflow changes to deliver timely, role-specific enablement. 

• Support enterprise readiness during periods of change by ensuring leaders and staff understand new expectations and can continue executing effectively. 

Adoption Reinforcement and Effectiveness Measurement (15%) 

• Track learning uptake, confidence, and effectiveness using participation data, feedback, and adoption signals. 

• Identify gaps in understanding or consistency and adjust learning approaches accordingly. 

• Partner with Product to align learning insights with roadmap decisions and adoption strategies. 

Executive, Executive Assistant, and Special Assistant Enablement (10%) 

• Serve as a strategic thought partner to executives and their support teams, helping shape how digital systems and workflows should operate to support leadership execution. 

• Own the design and effectiveness of enterprise enablement services for executives, Executive Assistants, and Special Assistants, ensuring access to structured learning, clear guidance, and hands-on support delivered by the Digital Workplace team. 

• Ensure executive and assistant enablement aligns with enterprise standards while remaining responsive to real-world leadership needs. 

About You 

You have: 

• 5+ years of experience in enterprise learning, enablement, digital adoption, or related roles. 

• Experience designing learning for complex, distributed organizations. 

• A strong ability to translate tools, workflows, and standards into clear, practical learning experiences. 

• Experience supporting organizations through significant digital change or platform transitions. 

• A learner-centered mindset and strong instincts for adult learning and behavior change. 

• Comfort working cross-functionally with Product, Technology, Talent, and executive stakeholders. 

• Strong facilitation, communication, and influence skills. 

• The judgment to balance enterprise consistency with local adaptation. 

• A commitment to College Board's mission and to improving outcomes for students. 

• Ability to travel 2-4 times a year on behalf of College Board business 

All positions at College Board require 

• A passion for expanding educational and career opportunities and mission-driven work. 

• Authorization to work in the United States for any employer. 

• Curiosity and enthusiasm for emerging technologies, with a willingness to experiment with and adopt new AI-driven solutions, and comfort learning and applying new digital tools independently and proactively. 

• Clear and concise communication skills, written and verbal. 

• A learner's mindset and a commitment to growth: welcoming diverse perspectives, giving and receiving timely, respectful feedback, and continuously improving through iterative learning and user input. 

• A drive for impact and excellence: solving complex problems, making data-informed decisions, prioritizing what matters most, and continuously improving through learning, user input, and external benchmarking. 

• A collaborative and empathetic approach: working across differences, fostering trust, and contributing to a culture of shared success. 

About Our Process 

• Application review will begin immediately and will continue until the position is filled. 

• While the hiring process may vary, it generally includes resume and application submission, a recruiter phone or video screen, a hiring manager interview, a performance exercise, a panel interview, a conversation with leadership, and reference checks. 

About Our Benefits and Compensation 

College Board offers a competitive benefits and compensation program that attracts top talent looking to make a difference in education. As a self-sustaining non-profit, we believe in compensating employees equitably in relation to each other, their qualifications, their impact, and the relevant market. 

The hiring range for a new employee in this position is $80,000 to $135,000. College Board differentiates salaries by location, so where you live will narrow the portion of this range in which you can expect a salary. 

Your salary will be carefully determined based on your location, relevant experience, the external labor market, and the pay of College Board employees in similar roles. College Board strives to provide our best offer up front based on this criteria. 

Your salary is only one part of all that College Board offers, including but not limited to: 

• A comprehensive package designed to support the well-being of employees and their families and promote education. Our robust benefits package includes health, dental, and vision insurance, generous paid time off, paid parental leave, fertility benefits, pet insurance, tuition assistance, retirement benefits, and more. 

• Recognition of exceptional performance through annual bonuses, salary growth over time through market increases, and opportunities for merit raises and promotions based on increased scope of responsibility. 

• A job that matters, a team that cares, and a place to learn, innovate, and thrive. 

You can expect to have transparent conversations about benefits and compensation with our recruiters throughout your application process. 

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