Executive Assistant to CEO and Head of Operations

Pocketbook Agency; San Francisco (CA); On-site; USD 120,000 - 180,000; Full time

Job summary

Pocketbook Agency is seeking an Executive Assistant to support the CEO and Head of Operations in a fast-growing tech startup. You will manage the CEO's calendar, organize materials, draft agendas, and coordinate high-level communications in a high-pressure environment.

You will partner with leadership to maximize efficiency, handle sensitive information with discretion, and plan complex travel. The role requires 10+ years supporting C-suite and a strong track record in startups.

Qualifications

• 10+ years of experience supporting C-suite executives, founders, or senior leadership teams in high-growth startups.
• Proven track record of strategic executive support beyond traditional calendar management.
• Demonstrated ability to anticipate needs, exercise sound judgment, and independently solve problems.
• Exceptional organizational skills with meticulous attention to detail and follow-through.
• Strong interpersonal and communication skills across teams and external partners.

Responsibilities

• Manage the CEO's complex calendar, coordinate meetings, prioritize appointments, and optimize time efficiency.
• Organize materials, draft agendas, and ensure information is readily available; anticipate conflicts and resolve before impacting leadership.
• Serve as a trusted partner to executive leadership to maximize efficiency and organizational effectiveness.
• Act as a primary point of contact for internal and external stakeholders with discretion and sound judgment.
• Plan and manage detailed travel itineraries, flights, accommodations, and logistics.
• Handle sensitive information with discretion and professionalism.
• Partner with Office Manager to ensure seamless executive support and operations.
• Support cross-functional initiatives to drive efficiency and execution.

Skills

Calendar management

Executive support

Cross-functional collaboration

Communication

Ambiguity handling

Multitasking

Google Workspace

Slack

Education

Bachelor's degree or higher

Tools

Google Workspace

Slack

Job description

We're looking for a sharp, proactive Executive Assistant to support the CEO and Head of Operations of a rapidly growing tech/software startup in San Francisco, CA. As a key partner to leadership, you'll manage complex schedules, coordinate high-level communications, and ensure seamless operations in a fast-moving environment. The ideal candidate thrives under pressure, anticipates needs before they arise, and builds strong relationships across teams and external partners.

Responsibilities

• Manage the CEO's complex calendar, coordinate meetings, prioritize appointments, and optimize time efficiency.
• Organize materials, draft agendas, and ensure all necessary information is readily available. Anticipate scheduling conflicts and proactively implement solutions before they impact leadership.
• Serve as a trusted partner to executive leadership, helping maximize efficiency, productivity, and organizational effectiveness.
• Act as a primary point of contact for internal and external stakeholders, handling communications with professionalism, discretion, and sound judgment.
• Plan and manage detailed travel itineraries, including flights, accommodations, and logistics, proactively addressing any issues.
• Handle sensitive information with the utmost discretion and professionalism.
• Partner with Office Manager to ensure seamless executive support and business operations.
• Support key initiatives by collaborating with cross-functional teams to drive efficiency and execution.

Qualifications

• 10+ years of experience supporting C-suite executives, founders, or senior leadership teams, specifically within a high-growth startup environment.
• Proven track record of providing strategic executive support beyond traditional calendar management.
• Demonstrated ability to anticipate needs, exercise sound judgment, and independently solve problems.
• Exceptional organizational skills with meticulous attention to detail and follow-through.
• Strong interpersonal and communication skills to build rapport across teams and with external partners.
• Comfortable operating with ambiguity and adapting quickly in a dynamic environment. Ability to multitask in a fast-paced environment with shifting priorities.
• Expert user of Google Workspace, Slack, and modern business productivity tools.
• A highly educated background preferred, with a focus on supporting startups.
• Experience in project management is a plus.

Location

Full time in office with flexibility, SF or NYC.