Executive & Personal Assistant to Founder — AI-Driven Ops

A stealth, venture-backed tech startup in NYC is looking for an Executive/Personal Assistant to support its founder. This is a high-touch, fast-paced role. It starts as a contract position and transitions to permanent once both sides assess long term fit.

This is a unique opportunity for a sharp, highly discreet, and operationally minded assistant who can blend high-level personal support, traditional executive assistance, and light office operations. The right person will bring strong judgment, speed, follow-through, and a modern, AI-forward approach to building systems.

• 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
• Identify repetitive tasks and improve workflows through AI tools, automation, and systems building
• Serve as a steady, resourceful operator in a fast-moving founder environment

• 5+ years of experience in EA, PA, or blended EA/PA support.
• Strong experience supporting a founder, executive, or high-net-worth principal.
• Proven judgment, discretion, and follow-through.
• Strong organization skills. You stay calm under pressure and move fast.
• A track record of building systems that improve operational efficiency.
• Comfort with AI tools and automation in your daily workflow.
• Ability to thrive in a startup environment with fluid hours and high expectations.
• Low ego, adaptability, and resilience.
• 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.

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

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

$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.