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

Workday•Pleasanton, CA

3d•Hybrid

About The Position

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.

Requirements

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.

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.