Executive/Personal Assistant to Startup Founder

Pocketbook Agency; New York (NY); On-site; USD 113,000 - 138,000; Full time

Job summary

Pocketbook Agency in New York City seeks a sharp, highly discreet Executive/Personal Assistant to support its founder across two closely connected startup businesses. This high-touch role blends executive support, personal logistics, events, and day-to-day coordination in a founder-led environment.

The position starts as a contract with the potential to become permanent after a mutual fit assessment. You will manage calendars, travel, residences, vendors, and payments, and build systems using AI

Qualifications

• 2+ years of EA/PA or blended EA/PA experience, startup or founder-led preferred.
• Strong interest in AI with ability to use AI tools beyond basic tasks.
• High energy, curiosity, resourcefulness and grind factor.
• Comfort with wearing many hats in a loosely structured environment.
• Excellent judgment, discretion, organization, and follow-through.

Responsibilities

• Provide high-level executive and personal support to the founder, including calendar management, scheduling, payments, billing, travel, and administrative coordination.
• Coordinate logistics across two affiliated NYC-based startup offices.
• Manage personal support needs, including residences, vendors, transportation, and occasional aircraft-related coordination.
• Support office operations, team logistics, and ad hoc projects across both businesses.
• Assist with founder-related events and activations, including nightlife, brand, university, and celebrity-facing events as needed.
• Build systems and improve workflows using AI tools, automation, and operational best practices.
• Anticipate needs, manage shifting priorities, and keep projects moving in a fast-paced environment.

Skills

Executive support

Calendar management

Travel logistics

Discretion

AI tools use

Tools

AI tools

Job description

A stealth, venture-backed technology company is seeking a sharp, highly discreet Executive/Personal Assistant to support its founder across two closely connected startup businesses.

This is a high-touch, fast-paced role for someone who thrives in a dynamic founder environment. The assistant will serve as a resourceful, boots-on-the-ground operator balancing executive support, personal logistics, events, and day-to-day coordination across both teams.

This role begins as a contract position and is expected to transition to permanent following a mutual assessment of long-term fit.

Responsibilities

• Provide high-level executive and personal support to the founder, including calendar management, scheduling, payments, billing, travel, and administrative coordination.
• Coordinate logistics across two affiliated NYC-based startup offices.
• Manage personal support needs, including residences, vendors, transportation, and occasional aircraft-related coordination.
• Support office operations, team logistics, and ad hoc projects across both businesses.
• Assist with founder-related events and activations, including nightlife, brand, university, and celebrity-facing events as needed.
• Build systems and improve workflows using AI tools, automation, and operational best practices.
• Anticipate needs, manage shifting priorities, and keep projects moving in a fast-paced environment.

Requirements

• Approximately 2+ years of EA, PA, or blended EA/PA experience; startup, tech, or founder-led experience strongly preferred.
• Strong interest in AI and a demonstrated ability to use AI tools beyond basic tasks.
• High energy, curiosity, resourcefulness, and a strong “grind factor.”
• Comfortable wearing many hats and operating with limited structure.
• Excellent judgment, discretion, organization, and follow-through.
• Able to stay calm under pressure and move quickly as priorities evolve.
• Low ego, adaptable, and eager to learn in a high-growth environment.
• Experience supporting founders, executives, events, vendors, households, or personal logistics is a plus.

Location & Hours

• Fully in-office in New York City.
• Must be flexible in schedule. Hours can range from 10am-9pm.
• Flexibility for occasional evening events is required.

Structure & Compensation

• Compensation: Up to $125,000, depending on experience, plus benefits.