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Robert Half Logo Robert Half · IT - Administration

Chief Of Staff

United States, Redwood City · Job Posted May 30, 2026
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Job Description

Robert Half is working with a rapidly growing leader in Enterprise AI and predictive analytics technology to identify a highly strategic and execution-oriented Chief of Staff to partner closely with the CEO during a pivotal stage of growth and transformation. This individual will serve as a trusted advisor and operational leader, driving cross-functional initiatives, improving organizational alignment, and helping execute high-priority business objectives across the company. The ideal candidate brings a blend of executive presence, analytical rigor, operational discipline, and the ability to thrive in a fast-paced, high-growth technology environment. This is an exceptional opportunity for someone who enjoys solving complex business challenges, influencing executive decision-making, and operating at the intersection of strategy, operations, and innovation within the AI and enterprise software space.

Job Responsibility

  • CEO Thought Partnership: Serve as a trusted advisor and sounding board to the CEO on strategy, prioritization, and the most important open questions facing the business. Pressure-test thinking with rigor, structure, and intellectual honesty.
  • Strategic Initiatives: Lead high-priority, cross-functional initiatives end-to-end — from problem definition and analysis through alignment and execution. Initiatives may span pricing strategy, market entry, organizational design, M&A diligence, or new product bets.
  • Executive Operating Cadence: Own the rhythms that drive alignment across the company, including executive leadership team meetings, OKR cycles, all-hands, and quarterly planning. Ensure decisions are documented, communicated, and followed through.
  • Decision Memos and Analysis: Translate complex, open-ended business problems into structured plans, decision memos, and data-driven recommendations the CEO and leadership team can act on within compressed timelines.
  • Technical Depth: Engage substantively with the product, platform, and data. Read code and architecture documents, query the data warehouse, and reason about technical tradeoffs alongside engineering leadership.
  • External Representation: Represent the CEO in select internal and external forums, including customer executive briefings, partner discussions, and executive recruiting.
  • Organizational Health: Identify gaps, bottlenecks, and broken processes before they surface elsewhere — and either drive resolution directly or assign the right owner.

Requirements

  • 8–12 years of progressive experience combining top-tier management consulting (McKinsey, Bain, BCG) and an operating role at a high-growth technology company
  • Bachelor's degree required, preferably in Computer Science, Engineering, Mathematics, Physics, or a related technical discipline
  • MBA from a top-tier program strongly preferred
  • Demonstrated technical fluency — able to engage credibly with engineering and product leaders on architecture, AI/ML, and data infrastructure topics
  • Exceptional structured problem-solving: ability to decompose ambiguous problems, build the underlying analysis, and produce executive-ready written recommendations under tight deadlines
  • World-class written and verbal communication, including experience drafting executive memos and presentations for senior leadership audiences
  • High-agency operator who defaults to action, navigates ambiguity without a playbook, and consistently closes loops without prompting
  • Discreet, low-ego, and trusted with highly sensitive information, decisions, and relationships
  • Genuine intellectual curiosity about enterprise AI and a long-term commitment to the mission
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