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 Workplace

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