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 solid 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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📌 Chief of Staff (Winnipeg)
🏢 Jobtailor
📍 Winnipeg