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Director Of Strategic Initiatives

Posted on June 25, 2025

Dublin, Ireland
0 - 0 USD (yearly)

Full Time

Your work days are brighter here.

At Workday, it all began with a conversation over breakfast. When our founders met at a sunny California diner, they came up with an idea to revolutionize the enterprise software market. And when we began to rise, one thing that really set us apart was our culture. A culture which was driven by our value of putting our people first. And ever since, the happiness, development, and contribution of every Workmate is central to who we are. Our Workmates believe a healthy employee-centric, collaborative culture is the essential mix of ingredients for success in business. That’s why we look after our people, communities and the planet while still being profitable. Feel encouraged to shine, however that manifests: you don’t need to hide who you are. You can feel the energy and the passion, it's what makes us unique. Inspired to make a brighter work day for all and transform with us to the next stage of our growth journey? Bring your brightest version of you and have a brighter work day here.

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About the Team

With teams located in the US, Canada, Ireland, and Latvia, the Workday Spend Product Development organization is dedicated to building the best Spend Management platform for Financials customers. Our strategy focuses on expanding our suite's capabilities, strengthening our full platform positioning, and enhancing the user experience for all Spend personas, including Expense Submitters, Buyers, and Suppliers.

Our products empower Procurement and Sourcing teams to proactively manage costs and mitigate risk, with a strong but not exclusive focus on the Healthcare Industry. Current key initiatives include integrating AI for Contract Intelligence and Intelligent Purchasing, improving the Expense Submitter Experience with features like real-time transactions, and driving overall engineering efficiency by reducing manual overhead through strategic operational improvements and leveraging AI and tooling initiatives across all our teams.

About the Role

Workday is seeking a Director of Strategic Initiatives (DoSI) to act as a pivotal strategic advisor and counsel to the Senior Director of Workday Spend Product Development. This critical role is designed to drive forward key strategic initiatives, ensuring the attainment of operational excellence across the organisation.

The DoSI will lead initiatives aimed at accelerating business operations and enhancing effectiveness and efficiencies within the Spend Development teams. A key responsibility will be to foster and maintain robust cross-departmental relationships, which are essential for enabling leadership success. The ideal candidate will possess a profound passion for driving continuous improvement and will thrive within an employee-first, customer-centric culture.

In this role, you will have the opportunity to:

Operational Excellence & Strategic Execution:
- Drive operational excellence by identifying and executing opportunities to optimise organisational systems and processes, while uniting multiple stakeholders to facilitate critical decisions.
- Define, lead, and contribute to process and change management initiatives for Spend Development teams.
- Provide thought leadership and assist in defining, planning, and orchestrating strategic business and operational initiatives, ensuring successful outcomes and clear visibility of status and progress.
Data, Metrics & Business Insights:
- Curate and communicate the overall narrative for business-related metrics through regular interaction with metric owners, proactively understanding data trends and insights.
- Monitor and analyse trends to provide critical insights, integrating these metrics into business and operations reviews.
Communication & Cultural Initiatives:
- Orchestrate and develop operational cadences and key communication strategies for the organisation.
- Coordinate and develop compelling content for team and org-wide meetings and events, as well as curating org-specific content for senior management reporting.
- Provide thought partnership and assist with defining, planning, and orchestrating culture-based initiatives across the team.
Organisational Development & Talent Management:
- Co-ordinate and lead Org Professional Development Programs.
- Develop and implement creative ways to cultivate all types of learning and innovation ideas throughout the organisation.
- Develop and implement creative ways to cultivate all types of recognition throughout the organisation, ensuring representation in Product and Corporate level recognition as appropriate.
Financial & Resource Management:
- Oversee budget spend to ensure optimal leverage of financial resources, including headcount, travel, professional development, and employee relations.
Cross-functional Collaboration & Program Management:
- Collaborate across the organisation to align Objectives and Key Results (OKRs), including managing cross-team communication, alignment, and proactive reporting.
- Program manage local initiatives with the teams, such as offsites and working with People & Purpose .
- Collaborate effectively with other Directors of Strategic Initiatives (DoSI) / Chiefs of Staff within the broader ecosystem, particularly concerning process change.

About You

Basic Qualifications

At least 10 years of experience in a Product Development environment, demonstrating a proven track record in:
- Developing and executing strategic priorities.
- Strategising and executing impactful change management initiatives.
- Project and Program Management, including leading multiple strategic programs and projects concurrently.
- Crafting and delivering executive-level presentations, demonstrating gravitas and the ability to communicate clear messages effectively across all organisational levels and roles.
- Managing a fiscal budget across multiple teams.

Other Qualifications

Strategic Acumen & Problem Solving:
- Demonstrated business acumen, including the keenness and quickness to understand and navigate complex business situations towards successful outcomes, with the ability to quickly connect disparate information.
- Proficiency in critical thinking and problem-solving, leveraging data from multiple sources, assessing diverse viewpoints, and making robust data-driven decisions and recommendations.
- Experience with risk mitigation strategies and implementation.
Interpersonal & Leadership Skills:
- A proven ability to build strong, impactful connections across diverse cross-functional teams, including Product, Technology, Services, and Sales.
- Exceptional facilitation skills, adept at navigating difficult situations and conversations, and skilled in delivering constructive feedback across all organisational levels.
- Demonstrated ability to influence leaders at all levels of the organisation.
- Experience in leading teams with a strong focus on achieving tangible outcomes and results.
Operational & Business Acumen:
- Extensive experience in managing operational excellence, encompassing the ability to delve into details, construct and communicate operational metrics, define clear success measures, and effectively gauge progress towards established goals.

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.

Are you being referred to one of our roles? If so, ask your connection at Workday about our Employee Referral process!

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