Director, Digital Workplace Training

College Board•New York, NY

2d•$80,000 - $135,000•Remote

About The Position

The Office of the CEO (OCEO) is a small, high-leverage enterprise team that operates at the center of College Board. Working directly with the CEO, President, and senior leaders, OCEO strengthens and accelerates mission impact by ensuring the organization moves in a coherent, disciplined, and aligned way. The office brings together executive leadership support and enterprise execution, connecting strategy to action and enabling leaders to focus on what matters most for students. 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. 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.

Requirements

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
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.

Responsibilities

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.
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.
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.
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.
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.