Sr. Director, AI Strategy & Enablement

OSV

3d•Remote

About The Position

OneSource Virtual is seeking a senior leader to own how the organization decides to use, govern, and scale AI. The role will develop and maintain a multi-year AI strategy and roadmap aligned with technology and business priorities, identify opportunities to improve operations and offerings, and turn selected experiments into repeatable capabilities. It will establish responsible-AI standards and risk reviews appropriate to sensitive customer and company data, working with IT leadership, security, legal, and data owners. The role will maintain visibility into AI use cases, ownership, data access, investment, and value; advise on tools, vendors, and partner opportunities; and establish measures and executive reporting to show what is working and what is not. It will guide adoption by enabling employees, sharing reusable patterns, capturing organizational knowledge, and working across business and technology teams. The position leads the AI strategy function as it forms, directs build work it owns, and sets standards and review practices for AI work across the organization, backed by IT leadership.

Requirements

Bachelor's degree in Computer Science, Engineering, Business Administration, or a related field.
10+ years of technology or innovation experience with increasing responsibility and strategic impact.
5+ years leading cross-functional initiatives, portfolios, or governance work, including budget awareness and stakeholder coordination.
Practical experience with AI, machine learning, or automation, including vendor evaluation and moving work from pilot to production.
Experience with governance, risk, or responsible-AI practices, ideally involving sensitive or regulated data.
Track record of measuring outcomes and improving results with data.
Hands-on fluency with current AI tools and experience building agents or prototypes.
Experience preparing and presenting strategy to senior executives.
AI strategy and roadmapping knowledge, including enterprise AI adoption, platforms, and the transition from experiment to production.
Ability to identify AI opportunities and make a case for them.
Governance and risk judgment, particularly for sensitive and regulated data.
Operating-model design experience or capability, including decisions, ownership, and accountability across teams.
Measurement and analysis skills, including setting baselines, selecting meaningful measures, and communicating uncertainty honestly.
Ability to influence and follow through across peers, functions, and executives, including holding owners to commitments.
Change and enablement skills, including learning, peer communities, and supporting voluntary adoption.
Technical fluency with current AI tools, including enough experience building agents or prototypes to establish credibility with builders.
Clear executive communication and stakeholder management skills.

Nice To Haves

Experience in SaaS, financial services, or HR and payroll technology.
Understanding of compliance and data privacy requirements, including international requirements.
Experience designing operating models or governance approaches.
Experience enabling adoption through learning and peer communities.
Experience developing partnerships with platform vendors and technology partners.
Programming or prototyping skills in Python or similar languages.

Responsibilities

Own and maintain a multi-year AI strategy and roadmap aligned with business and technology priorities, revising it as technology and evidence change.
Take positions on AI direction, make the case for them, and influence clear organizational decisions and outcomes.
Identify opportunities for AI to change business processes and offerings, monitor technology and market developments, make investment cases, and raise relevant issues to leadership early.
Discover and catalog process improvements across functions, identify automation opportunities, and selectively prototype to validate standards, patterns, or value before wider investment.
Maintain a current view of AI use cases, owners, data touched, and value produced; decide which initiatives, including vendor pilots, to support, scale, or retire.
Define risk-based responsible-AI governance with security, legal, and data owners, taking account of sensitive customer and company data and extending standards to agents and skills.
Ensure AI efforts receive review proportionate to their risk before proceeding.
Gain visibility into AI spending, advise on tools and vendor investments, and evaluate partner opportunities, including the Workday relationship.
Hold owners of AI initiatives accountable for commitments and escalate issues to leadership when commitments are not met.
Establish baselines and success measures, including effects on delivery capacity; track AI capability maturity and report results plainly.
Enable employees to use AI effectively, share reusable patterns, and capture tribal knowledge in forms usable by people and agents.
Build shared direction with technology and business leaders while respecting teams' ownership of AI use within established standards; address reasons teams avoid or work around sanctioned channels.
Work with IT leadership to define how AI standards operate day to day.
Prepare clear executive and company-wide updates on the roadmap, progress, and business impact.
Develop and lead the AI strategy function as it forms, work through partners across the company, direct build work owned by the role, and set standards and review practices for AI work built elsewhere.