AI Strategic Operations Director

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

Come join our team and help shape the future of AI at Workday!
Workday is a leader in enterprise-class, software-as-a-service (SaaS) Human Capital Management and Financial Management solutions. Our AI capabilities are central to our strategy, empowering customers to transform their businesses. The AI Services team is at the forefront of this transformation, responsible for building and delivering AI-powered solutions that drive customer value and business growth.
Our team brings a diverse range of skills from across product, engineering, and professional services. We're passionate about innovation and committed to excellence, working to Workday's core values of Customer Service and Integrity. We collaborate closely with our engineering, product, and sales teams to ensure that our customers are successful in adopting AI technologies and realizing their business objectives.

About the Role

You will be the driving force behind the operational strategy and execution for our AI Services organization. This is a critical role that will focus on maximizing customer value through strategic business leadership, financial rigor, and cross-functional collaboration. You will serve as a key partner to our leadership team, building the operational infrastructure needed to scale and innovate our AI services.

You’ll use your experience in strategic planning and operations to manage complex organizational changes, lead long-range planning initiatives, and ensure the successful delivery of our AI programs. If you are a self-starter with a passion for driving operational excellence and can thrive in a complex, fast-paced environment, this is the role for you.

About You

Core Responsibilities:

• Strategic Business & Operations Leadership: Drive operational execution to the strategic vision of our AI-powered services. You will ensure alignment across the organization and a focus on maximizing customer value.
• Financial Modeling & Optimization: Develop and maintain financial models and metrics. You will lead deep-dive analyses and drive continuous operational improvement across our AI services.
• Executive Workshops & Cross-Functional Collaboration: Design and facilitate strategic workshops with executives and cross-functional stakeholders. You will identify improvement opportunities, co-create innovative solutions, and enhance customer outcomes.
• Change Management & Organizational Transition: Lead and manage complex organizational changes, ensuring the effective adoption of new technologies, structures, and processes across the AI services organization.
• Executive-Level Communications & Alignment: Craft high-impact executive communications and business narratives. You will ensure leadership alignment, transparency, and clarity on service performance and direction.
• Organizational Design & Financial Justification: Shape the AI organizational structure and lead efforts to justify investments through data-driven business cases and strategic workforce planning.
• Planning and Portfolio Management: Oversee end-to-end delivery of complex programs, leveraging OKRs and quarterly cycles to ensure timely execution, ownership, transparency, and results.
• Performance Measurement: Establish and manage key performance indicators (KPIs) and lead OKR development and execution to foster accountability and measurable success at scale.
• AI M&A Integration: Lead the seamless integration of operational processes from acquired companies into the existing services organization. This includes ensuring business continuity and actively managing operations to validate and optimize integrated processes.

Basic Qualifications:

• 15+ years of experience in strategic operations, business planning, or a similar role, with a focus and understanding of software (SaaS) and professional services delivery.
• 5+ years of experience in a leadership role, driving operational strategy and tactical execution initiatives to achieve measurable improvement in efficiency, team performance and business outcomes.
• 8+ years of developing and maintaining Executive level relationships resulting in successful partnerships and strategic alignment.
• Project Management Certified

Other Qualifications:

• Proven experience working with and supporting a senior leadership or C-suite audience.
• Strong business acumen with the ability to analyze financial and market information to identify opportunities and drive strategic decision-making.
• Experience with financial modeling, forecasting, and business case development.
• Solid understanding of AI, machine learning, and/or emerging technologies is a plus.
• Exceptional communication and presentation skills, with the ability to create compelling business narratives and effectively align stakeholders.
• Proven ability to lead complex organizational change and manage large-scale programs.
• Demonstrated experience in a fast-paced, complex environment, with the ability to manage multiple priorities and deliver results.
• Experience with mergers and acquisitions (M&A) integration is highly valued.
• Strong internal engagement skills, with a focus on building relationships, driving customer satisfaction, and utilizing effective communication strategies to increase retention and sales growth, are essential.
• Ability to travel up to 50% domestic and globally

Workday Pay Transparency Statement

The annualized base salary ranges for the primary location and any additional locations are listed below. Workday pay ranges vary based on work location. As a part of the total compensation package, this role may be eligible for the Workday Bonus Plan or a role-specific commission/bonus, as well as annual refresh stock grants. Recruiters can share more detail during the hiring process. Each candidate’s compensation offer will be based on multiple factors including, but not limited to, geography, experience, skills, job duties, and business need, among other things. For more information regarding Workday’s comprehensive benefits, please click here.

Primary Location: USA.IL.Home Office Chicago Metro

Primary Location Base Pay Range: $183,100 USD - $274,700 USD

Additional US Location(s) Base Pay Range: $165,700 USD - $294,400 USD

Our Approach to Flexible Work

With Flex Work, we’re combining the best of both worlds: in-person time and remote. Our approach enables our teams to deepen connections, maintain a strong community, and do their best work. We know that flexibility can take shape in many ways, so rather than a number of required days in-office each week, we simply spend at least half (50%) of our time each quarter in the office or in the field with our customers, prospects, and partners (depending on role). This means you'll have the freedom to create a flexible schedule that caters to your business, team, and personal needs, while being intentional to make the most of time spent together. Those in our remote "home office" roles also have the opportunity to come together in our offices for important moments that matter.

Pursuant to applicable Fair Chance law, Workday will consider for employment qualified applicants with arrest and conviction records.

Workday is an Equal Opportunity Employer including individuals with disabilities and protected veterans.

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