Chief of Staff supporting the CEO at Private AI, focusing on operational management and system building. Work in hybrid mode based in Toronto, collaborating with executive leadership.
Responsibilities
Serve as the operational backbone for the CEO
Manage the CEO's calendar architecture
Implement an EA-managed email system
Create and maintain SOPs for operations
Be the primary point of contact between the CEO and internal teams
Document institutional knowledge
Support social media and external presence
Manage vendors and special projects
Handle high-priority projects as the company evolves
Requirements
2-5 years of experience in operations, chief of staff, executive assistant, or similar roles
Experience in early-stage software or AI company
Ability to turn messy brain dumps into clear tasks
Comfortable with ambiguity and judgment calls
Communicate clearly and directly—written and verbal.
Must be based in Toronto with willingness to be onsite 2-3 days/week
Familiarity with AI tools to accelerate work.
Bonus points for social media content management and operational documentation experience
Benefits
Opportunity to work with top-tier investors
Gain exposure to both company-building and investment decision-making
Participate in critical infrastructure for the AI era
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