CEO Strategy & Execution Lead

Sycamore; Palo Alto (CA); On-site; USD 150,000 - 230,000; Full time

Benefits offered by this job

Equity

Job summary

Sycamore in Palo Alto is seeking a Chief of Staff to work directly with the CEO, turning priorities into action and ensuring important work moves forward.

You will coordinate strategy and execution across the leadership team, prepare for meetings, and drive follow-through, with a bias for using AI and lightweight tools to move fast. This role is for someone early to mid-career, highly organized, an exceptional communicator.

Qualifications

• Typically 2–6 years in strategy consulting, investing, startup operations, or related analytical roles.
• Exceptional written and verbal communication.
• Strong judgment about context, audience, and tone when representing a CEO.
• Discretion with confidential information.
• High attention to detail and exceptional follow-through.
• Strong strategic and analytical instincts.
• Ability to work across executives, employees, customers, investors, and partners.
• AI-native mindset; willingness to build lightweight tools.
• Comfort with ambiguity and changing priorities.
• Low ego; toggle between high-level strategy and details.
• MBA or similar experience is helpful but not required.

Responsibilities

• Keep a clear view of the CEO’s priorities and ensure the work behind them moves.
• Prepare the CEO for important internal, customer, investor, and partner meetings with context, materials, and decisions.
• Turn meetings 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 without an obvious owner.
• Be AI-native; use AI, automation, and lightweight tools to work faster and better.

Skills

Strategy

Communication

Execution

Project management

Decision making

AI tooling

Education

MBA

Tools

AI automation

Job description

Sycamore in Palo Alto is seeking a Chief of Staff to work directly with the CEO, turning priorities into action and ensuring important work moves forward.

You will coordinate strategy and execution across the leadership team, prepare for meetings, and drive follow-through, with a bias for using AI and lightweight tools to move fast. This role is for someone early to mid-career, highly organized, an exceptional communicator.