Executive Assistant to CEO and Head of Operations

Pocketbook Agency; San Francisco (CA); On-site; USD 90,000 - 135,000; Full time

Job summary

Pocketbook Agency is seeking a sharp, proactive Executive Assistant to support the CEO and Head of Operations in San Francisco. You will manage complex schedules, coordinate high-level communications, and drive seamless operations in a fast-moving startup environment.

Ideal candidates have 10+ years in C-suite support within high-growth startups, exceptional organization, and a proven ability to anticipate needs while exercising sound judgment and discretion.

Qualifications

• 10+ years of experience supporting C-suite executives or senior leadership in high-growth startups.
• Proven ability to anticipate needs, exercise sound judgment, and independently solve problems.
• Excellent organizational skills with meticulous attention to detail and follow-through.

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 for leadership.
• Serve as a trusted partner to executive leadership, maximizing efficiency and organizational effectiveness.
• Act as primary point of contact for internal and external stakeholders with professionalism and discretion.
• Plan and manage detailed travel itineraries, including flights and accommodations.
• Handle sensitive information with utmost discretion and professionalism.
• Collaborate with Office Manager to ensure seamless executive support and operations.
• Support key initiatives by coordinating with cross-functional teams to drive efficiency.

Skills

Executive support

Calendar management

Communication

Relationship management

Ambiguity tolerance

Education

Bachelor's degree

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.