Workday · 1 month ago
Chief of Staff and Head of Operations, Office of the CTO
USA, CA, Pleasanton
Full-time
Hybrid
Director/Executive
$203K/yr - $360K/yr
10+ years expWorkday is a leading AI platform for managing people, money, and agents, and they are seeking a Chief of Staff and Head of Operations to support the Chief Technology Officer. This high-impact leadership role involves driving operational cadence, strategic execution, and cross-functional alignment across the technology functions, ensuring the CTO's time is optimized for the highest-impact priorities.
Artificial Intelligence (AI)Cloud ComputingEnterprise SoftwareHuman ResourcesSaaSSoftware
Responsibilities
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
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
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
Qualification
Required
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
Strong working knowledge of the modern software development lifecycle, technology organization structure (e.g., Platform, Architecture, AI/ML), and the enterprise technology landscape
Proven ability to communicate, present, and build trust with C-level executives and senior vice presidents
Exceptional organizational, planning, and program management skills with a proven track record of designing and running effective operational cadences (RoB)
Outstanding written and verbal communication skills, with the ability to distill complex technical and business topics into clear, concise executive narratives
Benefits
Workday Bonus Plan
Annual refresh stock grants
Company
Workday
Workday provides SaaS-based enterprise solutions for a company's human resources and financial management activities.
10001+ employees
H1B Sponsorship
Workday has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2025 (331)
2024 (388)
2023 (262)
2022 (503)
2021 (290)
2020 (229)
Funding
Current Stage
Public CompanyTotal Funding
$2.23BKey Investors
Elliott Management Corp.New Enterprise AssociatesGreylock
2025-09-16Post Ipo Equity· $2B
2012-10-12IPO
2011-10-24Series F· $85M
Leadership Team
Aneel Bhusri
CEO and Co-Founder
Peter Bailis
Chief Technology Officer
Recent News
2026-01-09
Company data provided by crunchbase