Director of Strategic Initiatives, Medium Enterprise

Posted:
3/2/2026, 11:16:57 AM

Location(s):
San Francisco, California, United States ⋅ California, United States ⋅ Washington, United States ⋅ Santa Clara, California, United States ⋅ Seattle, Washington, United States ⋅ Pleasanton, California, United States

Experience Level(s):
Expert or higher ⋅ Senior

Field(s):
Business & Strategy

Workplace Type:
Hybrid

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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

The Workday GO organization is a newly established, high-impact team within the broader Workday Growth Organization, dedicated to accelerating Workday's success in crucial, must-win market segments, with a particular focus on the Medium Enterprise (ME) business. Led by the General Manager (GM) of Workday GO, this team is responsible for aligning product strategy, Go-to-Market (GTM) execution, and operational excellence to drive step-change performance in these key markets. We operate with the focus and agility of an integrated business unit, backed by the resources and stability of Workday. The Director of Strategic Initiatives is a critical new leadership role designed to drive operational excellence throughout the ME business. This covers programs that range from Marketing and Sales to Security and Product. Come be part of our exciting team!

About the Role

As the Director of Strategic Initiatives (Business Operations), you are the strategic "force multiplier" for the General Manager of Workday GO. This is not just an operations role—it is a leadership position designed to help the GM see around corners in a complex, high-growth environment.

You will be the architect of our operational rhythm, transforming a matrixed, multi-functional organization into a high-velocity machine. Your mission is to provide the early line of sight—the "top-down, bottom-up" visibility—required to identify risks, bridge the gap between Product and Commercial teams, and ensure we are delivering flawlessly against our Medium Enterprise growth strategy.

Key Responsibilities

  • Strategic Navigation: Act as a high-level proxy and "navigator" for the GM, cutting through organizational complexity to ensure the business is performing to plan.

  • Operational Rhythm: Design and lead the cadence of the business (MBRs, QBRs, leadership offsites, and weekly reviews) to ensure cross-functional alignment from Marketing and Sales to Product and Security.

  • Matrix Orchestration: Bridge the gap between disparate teams—including traditional development and matrixed leadership—to ensure a unified approach to our "must-win" market segments.

  • Early Line of Sight: Implement rigorous reporting and "high-velocity infrastructure" that allows the leadership team to detect performance trends early and course-correct in real-time.

  • Executive Influence: Run complex work-streams across the Workday executive ecosystem, ensuring the GO organization remains integrated with the broader corporate strategy.

Why This Role is Critical

In a matrixed SaaS environment, the biggest risk is a lack of visibility. This role is the solution. By establishing a clear "Lead-to-Cash" operational framework and ensuring tight alignment between Product & Technology and our Commercial engines, you provide the structural integrity needed to achieve a step-change in performance for our Medium Enterprise business.

About You

Basic Qualifications

  • 8+ years experience in project or program management, envisioning, defining, and delivering impactful projects/programs at scale.

Other qualifications

  • Experience in operational management for an integrated business including process, tooling, and reporting ownership.
  • Demonstrated ability to communicate clearly and concisely to all levels of the organization.
  • Exceptional ability to drive Cross-Functional Alignment at both tactical and strategic levels across the organization, ensuring transparency, accountability, and effective execution for complex programs.
  • Shown ability to lead Meeting Facilitation optimally for executive-level meetings and strategic discussions, driving alignment, decisions, and actions.
  • Exceptional Proactive Thinking skills to anticipate program challenges and facilitate smooth program delivery.
  • Confirmed mastery in Stakeholder Engagement by building deep relationships with diverse and critical team members across the company and across the globe.
  • Strong analytical skills with the ability to design and handle reporting processes.
  • Deep understanding of enterprise SaaS across functions to deliver successful customer outcomes.


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.WA.Seattle


 

Primary Location Base Pay Range: $158,400 USD - $237,600 USD


 

Additional US Location(s) Base Pay Range: $143,400 USD - $254,600 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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