Chief of Staff / Chef(fe) de bureau

Digital Moment•Montreal, QC

16h•Remote

About The Position

We're looking for a Chief of Staff to work directly alongside our CEO. This role is for someone who thrives on making a whole organization run better rather than owning a single piece of it, and who wants their operational excellence to translate directly into impact for young people. As the organization grows, the CEO's focus is shifting outward towards partners, funders, and the communities served. The Chief of Staff's job is to make that possible by keeping strategy and execution connected across teams, leading the adoption of AI and automation, and taking on high-priority projects that don't fit neatly into any one department. When something spans multiple teams, lands without a clear owner, or needs to move fast, it comes to this role. This is a builder's role with a direct line to the CEO, a seat at the leadership table, and a mandate to shape how the organization works.

Requirements

Systems thinker who sees organizations as machines and instinctively spots where they leak time and energy.
Natural integrator who builds alignment across teams and influences people who don't report to you.
Hands-on with AI - experience rebuilding workflows around AI tools and creating working solutions through low-code platforms, scripting, or AI-assisted development.
Neutral broker with no departmental allegiance.
Discreet and trustworthy.
Low ego.
Comfortable with ambiguity.
Credible with senior leaders.
Relentless on follow-through.

Responsibilities

Connect strategy to execution by running the planning and priority-setting rhythm, tracking decisions through to completion, and steering cross-team initiatives from kickoff to finish.
Lead the internal AI and automation strategy, finding manual, repetitive work that eats teams' time, building or piloting solutions, getting people to use them, and showing the hours and capacity won back.
Extend the CEO's reach by preparing decisions, leading special projects, and representing the CEO in internal forums.
Sharpen how the organization operates by designing and running systems for leadership meetings, goal-setting and KPI tracking, reporting, and the discipline of clear decisions with clear owners.