Chief of Staff

Digital Moment

Chief of Staff at a Montreal-based charity enhancing operational efficiency and strategies for digital literacy programs. Collaborating with the CEO to execute high-priority projects.

Posted 7/28/2026full-timeRemote • 🇨🇦 CanadaLeadWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in leading AI and automation strategies while effectively managing cross-team initiatives and decision-making processes. Capable of designing systems that enhance organizational efficiency and alignment across diverse teams.

Highest-signal resume keywords

AI Strategy DevelopmentCross-Team CollaborationSystems ThinkingProject ManagementInfluencing Without Authority

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

AI-Assisted DevelopmentLow-Code PlatformsScriptingWorkflow OptimizationDecision Tracking

Soft Skills

TrustworthinessDiscretionProactive Follow-ThroughComfort with AmbiguityLow Ego

Industry Keywords

Organizational EfficiencyAlignment BuildingCross-Functional InitiativesExecutive CommunicationSpecial Project Leadership

About the role

Key responsibilities & impact

Connect strategy to execution.
Run our planning and priority-setting rhythm, track decisions through to completion, and steer cross-team initiatives from kickoff to finish.
Lead our internal AI and automation strategy.
Prepare decisions, lead special projects, and represent the CEO in internal forums so momentum never depends on one person's calendar.
Design and run the systems that keep everyone rowing in the same direction.

Requirements

What you’ll need

A systems thinker who sees organizations as machines and instinctively spots where they leak time and energy.
A natural integrator who builds alignment across teams and influences people who don't report to you.
Hands-on with AI - you've already rebuilt your own workflows around these tools and can create working solutions yourself, whether through low-code platforms, scripting, or AI-assisted development. We'll ask you to show us, not tell us.
A neutral broker with no departmental allegiance - every team should trust that you're optimizing for the whole.
Discreet and trustworthy - you'll handle sensitive information and act on the CEO's behalf every day.
Low ego - you're happiest when the people around you succeed, and you don't need the spotlight to know you're winning.
Comfortable with ambiguity - much of what reaches your desk arrives undefined, and you turn it into structure, priorities, and results.
Credible with senior leaders - you've operated at a level where directors and executives take you seriously.
Relentless on follow-through - proactive, decisive about what matters most, and allergic to loose ends.

Benefits

Comp & perks

20 days of annual vacation (including 5 days in December during office closure).
Group benefits including RRSP, parental top-up, medical and dental.
Working from home, and a flexible 35 hour work week.
10 annual wellness days.
Continuous learning and development opportunities.