Chief of Staff (AI)

TL;DR

Chief of Staff (AI): Supporting the executive team in operational and logistical execution with an accent on calendar architecture, prioritization, and project management. Focus on extending executive bandwidth, deploying modern AI tools to maximize output, and managing high-intensity operational scaffolding.

Location: Must be based in the US or Canada. Hybrid options available for candidates in New York City and Toronto.

Salary: $130,000–$145,000 USD

Company

AI-powered platform helping people access better jobs faster, focusing on workforce development and reducing economic inequality.

What you will do

• Manage executive calendars, prioritization, and gatekeeping with high judgment.
• Coordinate travel logistics, bookings, and expenses to minimize friction.
• Develop briefing documents and pre-reads to prepare the CEO for recurring meetings.
• Lead project work for executive offsites, travel, and senior-hire candidate experiences.
• Provide cross-functional operations support during organizational inflection points.
• Maintain strict discretion with sensitive information regarding finances and strategy.

Requirements

• 5+ years of experience supporting senior executives (founder/CEO), preferably in venture-backed companies.
• Must be based in the US or Canada.
• Demonstrated track record of managing project work alongside core administrative duties.
• Fluency with the modern AI toolkit for daily high-output productivity.
• Comfort with ambiguity and occasional flexibility outside standard business hours.

Nice to have

• Experience at a high-growth Series A through C startup.
• Background in workforce development, AI, or B2B SaaS.
• Proven skills in event production or offsite logistics.
• Basic project management discipline, including the ability to build tracking systems.

Culture & Benefits

• High-velocity, high-intensity environment with a strong drive for outcomes.
• Hybrid work flexibility for those located in NYC or Toronto.
• Remote-first approach with expected travel up to once per month.
• Commitment to diversity and an equitable, AI-enhanced hiring process.

Hiring process

• Online application followed by an initial screen with the Director of People & Culture.
• Interview with the Hiring Manager and a Performance Challenge.
• Final 1:1 interviews and final decision.