Chief of Staff

• Act as a trusted advisor and right-hand to the CEO
• Drive strategic alignment, operational execution, and organizational effectiveness
• Translate executive priorities into action
• Optimize internal processes and facilitate cross-functional collaboration
• Work closely with the CEO and executive team as a thought partner, problem-solver, and operational lead
• 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 business-status visibility to the CEO and leadership team
• Prepare board materials, executive presentations, and briefings for critical meetings
• Lead cross-functional initiatives and hand them off cleanly
• Identify, pilot, and roll out AI tools to streamline internal processes
• Shape communications for town halls, company updates, and speaking engagements
• Stand in for the CEO where appropriate
• 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

Requirements

• 5+ years of experience in executive operations, management consulting, corporate strategy, project management, or business operations
• Preferably experience 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 adopt AI tools
• Legal eligibility to work in Canada or the USA
• Ability to work on a hybrid model, typically three days per week at a hub location

Core Competencies

Demonstrates expertise in executive operations and strategic alignment, with a strong focus on optimizing internal processes and facilitating cross-functional collaboration. Proven ability to support C-level executives, manage multiple initiatives, and drive AI adoption within the organization.

Highest-signal resume keywords

• Executive Operations
• Strategic Thinking
• Project Management
• AI Fluency
• Communication Skills

Hard Skills

• Project Management
• Strategic Planning
• OKR Process Management
• Board Meeting Preparation
• Cross-Functional Initiative Leadership

Soft Skills

• Problem-Solving
• Organizational Skills
• Interpersonal Intelligence
• Influencing Skills
• Discretion

Industry Keywords

• Tech Environment
• SaaS
• C-Level Support
• Business Operations

Tools & Technologies

• AI Tools
• Presentation Software