Sr. Director, AI Strategy & Transformation

OSV

76d

About The Position

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.

Requirements

• Bachelor's degree in Computer Science, Engineering, Business Administration, or related field.
• 10+ years of technology or innovation leadership experience with demonstrated progression through increasing levels of responsibility and strategic impact.
• AI, machine learning, or automation implementation experience including strategic planning, vendor management, and enterprise-scale deployment.
• 8+ years of senior leadership experience managing large-scale transformation initiatives with responsibility for budget management, stakeholder coordination, and organizational change.
• Proven track record of leading complex client relationships and managing challenging situations during technology transformations with successful resolution and relationship preservation.
• Executive presentation and communication experience with ability to prepare and deliver strategic information to C-level executives, board members, and external stakeholders.
• Demonstrated expertise in metrics-based management and organizational performance measurement with track record of driving productivity improvements through technology adoption.
• Hands-on experience with AI development and prototyping including familiarity with major AI platforms, development tools, and implementation methodologies.

Nice To Haves

• Advanced AI and machine learning experience or certifications from major technology providers (AWS, Azure, Google Cloud) demonstrating technical depth and strategic understanding.
• Experience in SaaS, financial services, or HR technology industries with understanding of enterprise AI applications and compliance requirements.
• Industry thought leadership experience including publications, speaking engagements, and participation in AI strategy forums and professional associations.
• Advanced programming and prototyping skills in Python, R, or similar languages with ability to create functional AI demonstrations and proof-of-concept solutions.
• Partnership development experience with AI vendors, research institutions, and technology consulting organizations.
• International experience with understanding of global AI regulations, data privacy requirements, and cross-cultural technology adoption.
• Leadership development expertise with track record of developing next-generation technology leaders and AI specialists.

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.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: Bachelor's degree
• Number of Employees: 501-1,000 employees