Chief of Staff to the CEO
Hybrid (Palo Alto)Full-timePosted 3d ago
About the role
Chief of Staff role supporting the CEO to turn priorities into action, maintain momentum, and ensure important work gets done. Focused on leverage, clarity, follow-through, and AI-native working practices in a fast-moving startup environment based in Palo Alto.
Responsibilities
- Keep a clear view of the CEO’s priorities and make sure the work behind them keeps moving.
- Prepare the CEO for important internal, customer, investor, and partner meetings with the context, materials, and decisions needed going in.
- Turn meetings and conversations into action by capturing decisions, assigning owners, tracking commitments, and driving follow-through.
- Coordinate internal and external communication so the right people have the right context at the right time.
- Draft clear, concise communications on behalf of the CEO for employees, customers, investors, and other stakeholders.
- Jump into strategic questions, research, analysis, planning, and special projects as priorities change.
- Surface issues early, close open loops, and take ownership of work that does not yet have an obvious owner.
- Be AI-native. You use AI as a core part of how you work and are willing to build, automate, and create when needed.
Qualifications
- Typically 2-6 years of relevant professional experience in strategy consulting, investing, startup operations, or another analytical and strategic role.
- Exceptional written and verbal communication. You can take a messy set of ideas and turn them into something clear, concise, and useful.
- Strong judgment about context, audience, and tone, including when communicating on behalf of a CEO.
- Sound judgment and discretion when handling confidential company, employee, customer, and investor information.
- High attention to detail and exceptional follow-through. You keep track of commitments and make sure they get closed.
- Strong strategic and analytical instincts. You can quickly understand a new problem, structure it, and determine what matters.
- Comfortable working across senior executives, employees, customers, investors, and external partners.
- AI-native in how you work. You actively look for ways to use AI, automation, and lightweight tools to work faster and better.
- Comfortable with ambiguity, changing priorities, and taking on work outside a predefined job description.
- Low ego and willing to move between high-level strategic work and the small details required to make something happen.
- An MBA or similar experience can be helpful, but is not required.
Skills
Required:Strategic thinkingCommunication (written and verbal)Execution and follow-throughCross-functional coordinationAI/native tooling
Benefits
- Competitive cash compensation and meaningful equity in the company you are helping build.
Last updated Oct 22, 2026. Interested? Apply on the company site.
About Sycamore
The Trusted Agent Operating System
Sycamore: The trusted agent operating system for the enterprise.
Progressive Trust SystemAdaptive System GenerationContinuous ImprovementCollective IntelligenceTrust by designSecureCompliantAuditable
More open roles at Sycamore
- Forward Deployed Engineer3d agoHybrid (Palo Alto)
- Member of Product Staff3w agoHybrid (Palo Alto, CA) · Products
- Deployment Strategist1mo agoHybrid (Palo Alto) · Go-to-Market & Operations
- Marketing Intern2mo agoHybrid (Palo Alto) · Go-to-Market & Operations
- Domain Expert, Semiconductors & Infrastructure2mo agoPalo Alto, CA