Executive Support & Founder Operations Specialist

Jobtailor; New York (NY); Hybrid; USD 90,000 - 130,000; Full time

Job summary

Jobtailor is seeking an executive assistant to the CEO in New York/DC, supporting day-to-day operations and fast-paced decision-making. The role includes calendar management, meeting prep, and coordinating travel for multi-day engagements with federal and private-sector stakeholders.

You will draft briefs, talking points, and follow-ups, ensuring timely communication and organized handoffs. A candidate with startup or public-sector exposure will thrive in this high-ambiguity environment.

Qualifications

• 2–4 years supporting a founder or senior executive.
• Demonstrated ownership and ability to execute with incomplete information.
• Tight written communication for briefs, follow-ups, and summaries under time pressure.
• Fluency with AI tools, applied to speed and not as a substitute for judgment.
• Willingness to travel frequently, including multi-day trips to Washington, DC.
• Comfort with daily ambiguity and shifting priorities.
• Must split time between New York City and Washington, DC.
• Preferred: federal/public sector or startup experience.

Responsibilities

• Manage the CEO's day-to-day operations.
• Build advance meeting briefs from board materials and internal context.
• Travel to Washington, DC with the CEO for multi-day engagements.
• Attend meetings, take notes, and own resulting action items.
• Prepare talking points and logistics for speaking engagements and external events.
• Manage the CEO's inbox and calendar, including triage and drafting responses.
• Coordinate follow-ups with investors, partners, and federal stakeholders.
• Track open threads and close loops.
• Support recruiting for priority hires and interview prep.
• Deliver ad-hoc briefs, partner decks, and research.

Skills

Executive support

Written communication

AI tool fluency

Travel readiness

Time management

Job description

Jobtailor is seeking an executive assistant to the CEO in New York/DC, supporting day-to-day operations and fast-paced decision-making. The role includes calendar management, meeting prep, and coordinating travel for multi-day engagements with federal and private-sector stakeholders.

You will draft briefs, talking points, and follow-ups, ensuring timely communication and organized handoffs. A candidate with startup or public-sector exposure will thrive in this high-ambiguity environment.