Executive/Personal Assistant to Startup Founder

JRN 2567

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.

Pocketbook Agency is acting solely as a recruiting and placement firm for this position and is not the employer of record for this role unless otherwise explicitly stated. All hiring decisions, compensation, benefits, and employment terms are determined by the client employer. By applying, you acknowledge that submission of an application does not guarantee placement or employment.

Pocketbook Agency is an equal opportunity recruiting firm and does not discriminate in its recruiting, screening, or placement practices based on race, color, religion, sex, gender identity, sexual orientation, national origin, age, disability, veteran status, or any other protected characteristic under applicable law.