Chief of Staff

• Act as a trusted advisor and right-hand to the CEO
• Drive strategic alignment, operational execution, and organizational effectiveness
• Own executive meetings, business reviews, board meetings, and offsites, including agendas, pre-reads, decisions, and follow-through
• Own the OKR process end-to-end and provide the CEO and leadership team with an accurate view of business performance
• Prepare board materials, executive presentations, and briefings for critical meetings
• Lead cross-functional initiatives, including identifying, piloting, and rolling out AI tools to streamline internal processes
• Shape communications for town halls, company updates, and speaking engagements
• Stand in for the CEO where appropriate and determine what to decide or escalation
• Help the CEO prioritize and pressure-test decisions
• Champion AI adoption across the executive team by identifying use cases, vetting tools, running trainings, and coaching executives on AI-augmented workflows

Requirements

• 5+ years of experience in executive operations, management consulting, corporate strategy, project management, or business operations
• Experience preferably within a fast-paced tech or SaaS environment
• Proven experience supporting C-level executives or founders in a Chief of Staff, Business Manager, or Strategic Advisor role
• Strong strategic thinking and problem-solving capabilities
• Exceptional written and verbal communication skills
• Highly organized and detail-oriented
• Ability to manage multiple initiatives simultaneously under tight deadlines
• High EQ and interpersonal intelligence
• Ability to influence, mediate, and build trust across all levels of the organization
• Absolute discretion and professionalism in handling sensitive and confidential information
• AI fluency and ability to identify and implement practical AI use cases
• Legally eligible to work in Canada or the USA

Core Competencies

Demonstrates expertise in executive operations and strategic alignment, with a strong focus on AI adoption and organizational effectiveness. Proven ability to support C-level executives through effective communication, project management, and cross-functional leadership.

Highest-signal resume keywords

• Executive Operations Experience
• Strategic Thinking
• AI Fluency
• C-Level Support
• Project Management

ATS Optimization Keywords Hard Skills

• Project Management
• Strategic Planning
• AI Implementation
• OKR Process Management
• Data Analysis
• Business Performance Metrics
• Executive Presentation Preparation
• Cross-Functional Leadership
• Board Meeting Preparation
• Operational Execution

Soft Skills

• Exceptional Communication
• High Emotional Intelligence
• Organizational Skills
• Influencing Skills
• Problem-Solving

Industry Keywords

• Tech Environment
• SaaS
• Management Consulting
• Corporate Strategy
• Business Operations

Tools & Technologies

• AI Tools
• Presentation Software
• Project Management Software
• Collaboration Tools
• Data Visualization Tools

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Ul

• Act as a trusted advisor and right-hand to the CEO
• Drive strategic alignment, operational execution, and organizational effectiveness
• Own executive meetings, business reviews, board meetings, and offsites, including agendas, pre-reads, decisions, and follow-through
• Own the OKR process end-to-end and provide the CEO and leadership team with an accurate view of business performance
• Prepare board materials, executive presentations, and briefings for critical meetings
• Lead cross-functional initiatives, including identifying, piloting, and rolling out AI tools to streamline internal processes
• Shape communications for town halls, company updates, and speaking engagements
• Stand in for the CEO where appropriate and determine what to decide or escalation
• Help the CEO prioritize and pressure-test decisions
• Champion AI adoption across the executive team by identifying use cases, vetting tools, running trainings, and coaching executives on AI-augmented workflows

Li

5+ years of experience in executive operations, management consulting, corporate strategy, project management, or business operations

P

Demonstrates expertise in executive operations and strategic alignment, with a strong focus on AI adoption and organizational effectiveness. Proven ability to support C-level executives through effective communication, project management, and cross-functional leadership.

Work Hours

Full Time