AI-Forward Executive/Personal Assistant

A tech startup in NYC is looking for an Executive/Personal Assistant to support its founder. This is a high-touch, fast-paced role.

This role is built for someone who thinks in systems and reaches for AI first. You need genuine curiosity about AI tools, a fast learning curve, and the drive to build smarter processes from day one. The founder wants a right hand who treats AI as a core part of how the job gets done, not an add-on.

Responsibilities:

• Use AI tools and automation to handle scheduling, correspondence, research, and reporting
• Build and refine systems that make the founder’s day-to-day faster and cleaner
• Provide high-level executive support, including scheduling, payments, billing, and administrative coordination
• Manage personal support for the founder, including oversight of residences, staff and vendor coordination, transportation logistics, and occasional aircraft-related coordination
• Support light office operations and day-to-day team logistics
• Spot repetitive tasks and eliminate them through automation and smart tooling
• Serve as a steady, resourceful operator in a fast-moving founder environment

Requirements:

• Genuine curiosity about AI and a habit of using it in daily work — this matters more than years of experience
• Some experience in EA, PA, or blended EA/PA support (open to candidates earlier in their career)
• Strong organization skills. You stay calm under pressure and move fast
• Low ego, adaptability, and resilience
• Comfort with ambiguity and a fast-changing environment
• Strong fit for a close-knit, high-performance office
• Experience in startup, tech, venture, or founder-led environments preferred but not required
• Exposure to household, staff, or vendor management preferred but not required

Location: Fully in-office in Tribeca, 11:00 AM – 9:00 PM

Structure: Contract-to-hire. The role transitions to full-time

Compensation: $110,000, depending on experience + 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.