Sr. Director, AI Strategy & Enablement

OneSource Virtual (OSV) has worked exclusively with Workday customers since 2008 to deliver compliant, in-tenant technology and expert services to automate the administrative, transactional tasks of payroll, taxes, earned wage access, accounts payable, and benefits. With over 1,500 customers, 92% retention, and $225+ billion in treasury movement annually, OSV helps organizations maximize their Workday investment and operate it with confidence. Payroll, benefits, and finance solutions — all in one place. 

AI is part of how OneSource Virtual innovates and runs. This role owns how we decide to use, govern, and scale it. It builds the strategy and a multi-year roadmap, finds where AI can change how we work and what we offer, turns experiments into repeatable capability, and sets the standards that keep the work safe given the sensitivity of the data we handle, backed by IT leadership. It shows leadership evidence of what is paying off and what isn't. The role works across technology and the business, with teams owning how they use AI within the standards this role sets.

Essential Functions

• Own the AI strategy and roadmap. Build and maintain a multi-year view that moves us from scattered experimentation toward AI embedded in how we work, aligned with technology and business priorities, and revise it as the technology and our evidence change.
• Hold a clear point of view and influence outcomes. Take positions on AI direction, make the case for them, and move decisions toward clear outcomes across the organization.
• Identify where AI can change how we work and what we offer, and keep watch on how the technology and the market are moving. Make the case for the bets worth making, and bring what matters to leadership early.
• Surface use cases from the people doing the work, and prototype selectively. Discover and catalog process improvements across functions, bring forward automation opportunities worth pursuing, and build to prove a standard, a pattern, or a value case before wider investment.
• Keep a clear, current view of AI use. Know what exists, who owns it, what data it touches, and what value it produces, and decide what to back, scale, or retire, including vendor pilots, on consistent terms.
• Set responsible-AI standards and risk review. Define a risk-based approach to governance with security, legal, and data owners, reflecting the sensitivity of the customer and company data we handle. Extend it to agents and skills, and see that AI efforts are reviewed in proportion to their risk before they proceed.
• Guide AI investment. Gain visibility into where AI spend sits across the company, advise on AI tool and vendor investments, and evaluate partner opportunities, including the Workday relationship.
• Hold the owners of AI efforts to their commitments, and raise issues to leadership when they aren't met.
• Establish how value is measured. Set a baseline, including the effect on delivery capacity, and a small set of agreed success measures, track how our AI capability matures over time, and report plainly on what is working and what is not.
• Enable people and capture what works. Help people use AI well, spread reusable patterns, and turn concentrated tribal knowledge into something people and agents can use.
• Partner across the business, and make the sanctioned path the easy one. Build shared direction with leaders in technology and across the business, respect that teams own how they use AI within the standards this role sets, and understand why teams hold back or work around official channels so the causes get addressed instead of relying on mandates alone.
• Shape how it works in practice. Work with IT leadership to define how these standards operate day to day.
• Communicate with executives and across the company. Prepare clear updates on the roadmap, progress, and business impact.
• Build the team. Develop and lead the AI strategy function as it forms.

Competencies

• AI strategy and roadmapping with practical knowledge of enterprise AI adoption, platforms, and what it takes to move from experiment to production.
• Opportunity sensing: spotting where AI changes the work or the offer, and making the case for it.
• Governance and risk judgment, especially for sensitive and regulated data.
• Operating-model design: how decisions, ownership, and accountability work across teams.
• Measurement and analysis: setting baselines, choosing measures that mean something, and being honest about uncertainty.
• Influence and follow-through across peers, functions, and executives, including holding owners to commitments.
• Change and enablement: learning, peer communities, and adoption that people choose.
• Technical fluency with current AI tools, including building agents or prototypes, enough to earn credibility with builders.
• Clear executive communication and stakeholder management.

Supervisory Responsibility

Leads the AI strategy function as it forms and works through partners across the company. Directs build work where the role owns it, and sets standards and review practices for AI work built elsewhere in the organization, backed by IT leadership.

Qualifications and Experience

• 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 building agents or prototypes.
• Experience preparing and presenting strategy to senior executives.

Preferred Skills

• Experience in SaaS, financial services, or HR and payroll technology, with an 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.
• Partnership development with platform vendors and technology partners.
• Programming or prototyping skills in Python or similar languages.

#LI-REMOTE

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.