Chief of Staff (AI)

TL;DR

Chief of Staff (AI RFP automation): Serve as the CEO's strategic partner and force multiplier with an accent on growth projects, cross-functional initiatives, and operations scaling. Focus on driving high-priority strategic initiatives, fundraising support, and special projects like customer success frameworks in a high-growth GovCon AI platform.

Location: Onsite in New York City or Washington DC five days a week. U.S. Citizen required to handle sensitive GovCon data.

Company

Well-capitalized AI platform ($5M+ from Y Combinator and others) helping government contractors automate RFP responses, based in NYC, with 5x revenue growth toward $10M ARR.

What you will do

• Lead high-priority cross-functional projects, especially in growth marketing.
• Provide executive support: act as CEO sounding board, ghostwrite communications, proxy in meetings.
• Assist with fundraising materials and investor relations reporting.
• Tackle special zero-to-one projects like customer success frameworks or GovCon positioning.
• Oversee hiring for key roles and maintain high-intensity NYC/DC office culture.

Requirements

• 2–5 years high-performance experience in management consulting, investment banking, VC, or high-growth operator role.
• Strategic breadth to handle board decks and granular data analysis.
• Hyper-organized, proactive problem-solver who anticipates bottlenecks.
• Strong communicator able to explain AI and GovCon concepts clearly.
• U.S. Citizen able to work onsite in NYC or DC five days/week.

Nice to have

• Experience in GovCon or federal procurement.
• Technical literacy in LLMs and AI agentic workflows.
• Prior Chief of Staff or Founder’s Associate role.

Culture & Benefits

• High-intensity, mission-driven office culture in NYC/DC.
• Focus on scaling operations amid rapid growth (5x revenue, 10x DAU).
• Opportunity to impact strategic direction in well-funded startup.