Chief of Staff and Head of Operations, Office of the CTO

Chief of Staff and Head of Operations, Office of the CTO Scroll down to find an indepth overview of this job, and what is expected of candidates Make an application by clicking on the Apply button. Join to apply for the Chief of Staff and Head of Operations, Office of the CTO role at Jobs via Dice 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 Workday is the enterprise AI platform for managing people, money, and agents. Workday unifies HR and Finance on one intelligent platform with AI at the core to empower people at every level with the clarity, confidence, and insights they need to adapt quickly, make better decisions, and deliver outcomes that matter. Workday is used by more than 11,000 organizations around the world and across industries — from medium-sized businesses to more than 65% of the Fortune 500. For more information about Workday, visit . About The Role This is a high-impact leadership role and critical executive partner to the Chief Technology Officer (CTO) . The Chief of Staff and Head of Operations is the central nervous system of the CTO organization, responsible for driving the operational cadence, strategic execution, and cross-functional alignment of all technology functions. The role acts as a trusted advisor, strategic filter, and organizational linchpin, ensuring the CTO's time is optimized for the highest-impact priorities. You will drive efficiency and alignment across the entire technology team, which spans AI, Architecture, Platform, Experiences, and Design , enabling Workday to continuously deliver innovative, cloud-based enterprise solutions for Finance and HR. Key Responsibilities Operational Cadence and Execution (Head of Operations) Manage the Rhythm of Business (RoB): Design, manage, and continuously optimize the CTO organization's operating rhythm, including leadership staff meetings, business reviews, operational reviews, and executive offsites. Drive Accountability: Institute and manage a clear, repeatable process for tracking all executive decisions and action items, ensuring timely and effective execution by the CTO's leadership team. Track and Communicate Progress: Develop, maintain, and synthesize insights from simple, clear dashboards to track key initiatives, product goals, and organizational health metrics. Proactively identify and highlight critical risks for the CTO. Lead Internal Communications: Own the internal communications strategy for the CTO organization, including all-hands meetings, internal announcements, and leadership messages to ensure a clear, consistent, and inspiring narrative. Align Key Partners: Serve as the primary operational point of contact, building strong alignment and partnership with EAs, other Chiefs of Staff, and senior leaders across the broader Product & Technology organization. Executive Partnership (Chief of Staff) Optimize Executive Focus: Partner closely with the CTO's Executive Assistant to strategically manage the CTO's calendar, agenda, and priorities, ensuring time is efficiently allocated to the most critical strategic activities. Serve as Proxy and Filter: Act as the first point of contact for inbound requests and escalations to the CTO. Triage, resolve, or delegate issues as needed to protect the CTO's focus time. Ensure Meeting Readiness: Proactively prepare the CTO for all key meetings (internal, customer, partner, and strategic). This includes defining clear agendas, compiling comprehensive pre-read materials, and driving all follow-up actions. Represent the CTO: Attend key internal and external meetings on behalf of the CTO, synthesizing information, communicating official decisions, and driving progress with stakeholders. Strategic Planning and Initiatives Lead Strategic Analysis: Conduct focused research, analysis, and deep dives on specific, high-priority topics to support executive decision-making (e.g., new technology trends, competitive analysis, M&A preparation, or internal organizational design). Manage Special Projects: Lead and execute high-priority, cross-functional projects on behalf of the CTO. These initiatives often fall outside day-to-day operations and require dedicated executive oversight to successfully launch and transition to a long-term owner. Connect the Organization: Build strong, trusted relationships across the entire CTO organization and identify and help resolve cross-functional friction points between engineering, product, and design teams. Foster Team Culture: Partner with HR and the leadership team to develop and execute programs that build a strong, connected, inclusive, and high-performing engineering and design culture, aligned with Workday's core values. About You Experience: Minimum of 10+ years of progressive experience, with at least 3-5 years in a Chief of Staff, Head of Operations, Strategic Program Management, or similar executive-facing role within a large-scale SaaS or Enterprise Technology company. Technical Acumen: Strong working knowledge of the modern software development lifecycle, technology organization structure (e.g., Platform, Architecture, AI/ML), and the enterprise technology landscape. Executive Presence: Proven ability to communicate, present, and build trust with C-level executives and senior vice presidents. Organizational Management: Exceptional organizational, planning, and program management skills with a proven track record of designing and running effective operational cadences (RoB). Communication: Outstanding written and verbal communication skills, with the ability to distill complex technical and business topics into clear, concise executive narratives. 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.CA.Pleasanton Additional US Location(s) Base Pay Range: $202,900 USD - $360,500 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. Are you being referred to one of our roles? If so, ask your connection at Workday about our Employee Referral process At Workday, we value our candidates' privacy and data security. Workday will never ask candidates to apply to jobs through websites that are not Workday Careers. Please be aware of sites that may ask for you to input your data in connection with a job posting that appears to be from Workday but is not. In addition, Workday will never ask candidates to pay a recruiting fee, or pay for consulting or coaching services, in order to apply for a job at Workday. xrczosw Seniority level Executive Employment type Full-time Job function Administrative Industries Software Development Referrals increase your chances of interviewing at Jobs via Dice by 2x Sign in to set job alerts for “Chief of Staff” roles.