Executive Assistant - CEO in San Jose at Wing Assistant

We are looking for a high-leverage Executive Assistant to act as a strategic right hand to our CEO. This is not a typical administrative position. Beyond handling calendar management and travel coordination in a fast-paced, chaotic environment, you will play an active role in driving operational efficiency.

We need a clear-thinking, proactive problem solver who can jump right in without needing hand-holding. You will analyze data, build reports, identify operational gaps, and bring solutions to the table before issues arise.

1. Executive Operations & Gatekeeping

• Act as the primary point of contact and buffer for the CEO, managing internal and external communications with tact and judgment.

• Maintain complete situational awareness of the CEO’s priorities, deadlines, and ongoing projects.

• Manage complex, fluid calendars across multiple time zones, adjusting dynamically to continuous travel schedule changes.

• Handle seamless international travel arrangements, itineraries, and logistics.

2. Data Analysis & Business Intelligence

• Gather data across departments to create clear, actionable executive reports, dashboards, and presentations.

• Continuously audit workflows and metrics to identify gaps, inefficiencies, and areas for process improvement.

• Conduct research and synthesize complex information into quick, digestible briefs for decision-making.

3. Financial & Administrative Support

• Assist with financial tracking, expense management, budget auditing, and financial reporting.

• Monitor key financial indicators and track cross-departmental deliverables to ensure projects remain on budget and on schedule.

• Handle confidential business and financial information with high discretion.

• Turnkey Capability: Proven experience as an Executive Assistant, Chief Of Staff, Business Operations Manager, or Strategic Coordinator. You can drop into a fast-moving environment on Day 1 without requiring extensive training.

• High IQ & Analytical Thinking: Exceptional logic and problem-solving ability. You don't just report data; you understand what the numbers mean and recommend action.

• Proactive & Autonomous: You anticipate needs before they are voiced and actively look for ways to lighten the CEO's operational load.

• Chaos Tolerance: High adaptability, mental resilience, and composure in fast-changing, high-pressure environments.

• Financial Literacy: Comfort with numbers, spreadsheets, financial statements, and basic business finance principles.

• Time Zone Agility: Willingness and technical setup to work asynchronously and align with the CEO’s shifting global schedule.

• Tech Savvy: Advanced proficiency in modern workspace tools (e.g., Claude, Notion, Slack, Google Workspace, Excel/Google Sheets, project management platforms).