- 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 Setting
- SaaS
- Management Consulting
- Corporate Strategy
- Business Operations Tools & Technologies - AI Tools
- Presentation Software
- Project Management Software
- Collaboration Tools
- Data Visualization Tools

📌 Chief of Staff (Vancouver)
🏢 Jobtailor
📍 Vancouver