Sr. Director, AI Strategy & Transformation

Senior Director of Ai Strategy & Transformation

OneSource Virtual (OSV) has helped more than 1,000 Workday customers take their teams from transactional to transformational with innovative technology and services for HR, payroll, and finance. Founded in 2008, OSV is the leading exclusive provider of Business-Process-as-a-Service (BPaaS) solutions for Workday, delivering services with unparalleled choice, unwavering commitment, and uncompromising support. OneSource Virtual's global headquarters is located in Dallas, Texas, with additional locations across North America and Europe.

The Senior Director of AI Strategy & Transformation will lead OneSource Virtual's enterprise-wide artificial intelligence adoption initiative, driving strategic implementation of AI technologies across all departments and business functions. This executive role requires a visionary leader who can coordinate communication plans across multiple groups, execute complex client messaging strategies, and control high-stakes meetings while managing budgets for AI transformation initiatives. The Senior Director will prepare executive-level presentations, identify and mentor successors using metrics-driven approaches, and implement advanced tracking systems to measure AI adoption success. This position demands exceptional leadership during organizational change, the ability to hold multiple groups accountable, and strategic delegation skills while maintaining minimal day-to-day operational involvement. The role combines deep AI expertise with executive leadership capabilities to position OneSource Virtual at the forefront of AI-driven business transformation.

Essential Functions / Duties / Responsibilities

• Coordinate communication plans with other groups to ensure seamless AI adoption strategies across technology, operations, customer service, sales, HR, legal, and executive teams while maintaining alignment with business objectives.
• Guide strategic conversations toward clear decisions and implementable solutions, ensuring productive outcomes in AI strategy sessions, vendor evaluations, and cross-departmental implementation planning.
• Understand and manage the budget for AI transformation initiatives, including technology procurement, training investments, development resources, and ROI measurement across the organization.
• Prepare and format information to be delivered to executives, creating compelling presentations on AI strategy, implementation progress, competitive advantages, and business impact metrics.
• Identify and actively mentor successors using metrics, developing next-generation AI leaders through measurable development programs and succession planning initiatives.
• Implement and enhance metric-based tracking and success measurements across AI adoption groups and advocate adoption of measurement frameworks in similar transformation initiatives.
• Maintain clearly articulated opinions on AI strategy and influence outcomes toward strategic AI adoption positions across the organization and industry.
• Demonstrate effective planning and negotiation skills during periods of organizational change and technology disruption, maintaining transformation momentum under complex conditions.
• Hold multiple groups accountable including AI working groups, departmental implementation teams, and vendor partners producing work in coordination with transformation initiatives.
• Evaluate, recommend, and procure AI training materials for each department, assessing organizational needs and ensuring effective knowledge transfer and skill development across all business functions.
• Discover and catalog process improvements across the organization through systematic analysis, identifying AI automation opportunities and prioritizing initiatives based on business impact and feasibility.
• Develop AI solution prototypes to validate approaches, demonstrate value propositions, and guide strategic decisions on technology adoption and implementation methodologies.
• Lead development resources to build AI solutions, directing technical teams in implementing strategic AI initiatives while ensuring alignment with business objectives and quality standards.
• Delegate tasks to direct and indirect reports with limited hands-on involvement in day-to-day operations, intervening strategically when senior leadership is required for AI initiatives.
• Identify and measure group-level productivity improvements resulting from AI adoption, implementing data-driven optimization strategies and ROI measurement frameworks.
• Exhibit senior leadership behaviors with staff, combat resistance to AI adoption, and actively seek innovative solution recommendations from transformation teams and external partners.

Competencies

Supervisory Responsibility

This role has oversight responsibility for AI transformation initiatives across the organization, including Directors, Managers, development teams, and external consultants. Responsibilities include strategic leadership, resource allocation, cross-functional coordination, and vendor management for AI implementation projects.

Qualifications and Experience

Preferred Skills

You are encouraged to learn and share ideas when you join the OneSource Virtual team. We reward innovative thinking, fresh perspectives, creative collaboration, and hard work. As an organization experiencing routine strategic growth, we are always on the lookout for intelligent, talented, and forward-thinking professionals to join our team. OSV employees enjoy a values-based culture, upward mobility, and professional development with opportunities of all kinds.