Sr Director, Strategic Initiatives

Your work days are brighter here.

We’re obsessed with making hard work pay off, for our people, our customers, and the world around us. As a Fortune 500 company and a leading AI platform for managing people, money, and agents, we’re shaping the future of work so teams can reach their potential and focus on what matters most. The minute you join, you’ll feel it. Not just in the products we build, but in how we show up for each other. Our culture is rooted in integrity, empathy, and shared enthusiasm. We’re in this together, tackling big challenges with bold ideas and genuine care. We look for curious minds and courageous collaborators who bring sun-drenched optimism and drive. Whether you're building smarter solutions, supporting customers, or creating a space where everyone belongs, you’ll do meaningful work with Workmates who’ve got your back. In return, we’ll give you the trust to take risks, the tools to grow, the skills to develop and the support of a company invested in you for the long haul. So, if you want to inspire a brighter work day for everyone, including yourself, you’ve found a match in Workday, and we hope to be a match for you too.

About the Team

At Workday, the Enterprise Planning & Performance team acts as the connective tissue linking all functions to work towards a shared set of priorities. We own the cycle of planning, executing, and analyzing company progress, translating high-level strategy into tangible actions, measurable results, and driving accountability. We are building this capability to support Workday, a newly minted S&P 500 company, through its next phase of growth. Our team embraces an agile mindset, evangelizes an AI-first, data-driven approach, and has a passion for continuous improvement.

About the Role

We are seeking a Senior Director to lead our Strategic Initiatives team. This is a critical executive leadership role responsible for ensuring the successful execution of Workday's most important and complex cross-functional initiatives. You will be accountable for the business outcomes of our largest strategic programs, from launching new ventures to steering at-risk projects back on track. You will lead a team of high-caliber execution leaders and partner with senior executives across the company to turn our most ambitious strategic goals into reality.

Key Responsibilities:

• Lead a high-performing team of Principals and Senior Managers, providing mentorship and guidance to drive the execution of a diverse portfolio of strategic initiatives.

• Take co-ownership of business outcomes for major company initiatives, supporting programs from initial launch to full-scale execution.

• Provide hands-on executive leadership for a portfolio of flagship initiatives, short-term task forces, and critical interventions.

• Drive "path to green" SWAT interventions for at-risk initiatives by identifying key blockers, driving resolution with stakeholders, and developing clear recovery plans.

• Manage senior executive relationships, ensuring cross-functional alignment between product, GTM, and financial targets to facilitate decision-making.

• Establish and monitor standards for initiative progress, outcomes, and risks across the portfolio.

• Oversee diverse initiative support models, ranging from launching new strategic programs to leading targeted interventions for critical business opportunities.

About You

Basic Qualifications:

• 10+ years of progressive experience in corporate strategy, business operations, or program management.

• 10+ years of experience in Strategy Consulting and/or Strategic Finance.

• Extensive knowledge of enterprise software/SaaS industry strongly preferred.

Other Qualifications:

• Team Leadership: A track record of hiring, developing, and leading teams of versatile, high-impact program leaders and strategic thinkers.

• Executive Credibility & Influence: Proven experience building relationships with and influencing senior executive leaders on complex business challenges.

• Structured Problem Solving: A strong toolkit for diagnosing performance issues, developing hypotheses, and structuring data-driven analysis to create actionable recommendations.

• Business & Organizational Acumen: Deep understanding of how to navigate a complex, matrixed organization to get things done and lead impactful change.

• Portfoli