Location: Remote

Position Type: Permanent

Reports to: CEO

About the role

We're looking for a Chief of Staff to work directly alongside our CEO - 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 we grow, our CEO's focus is shifting outward: toward partners, funders, and the communities we serve. Your job is to make that possible. You'll keep strategy and execution connected across teams, lead our adoption of AI and automation, and take on the 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 you.

This is a builder's role. You'll have a direct line to the CEO, a seat at the leadership table, and a mandate to shape how the organization works — not just keep it running.

What you'll do

- 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. Where work tends to slow down at the handoff points between departments, you keep it moving.
- Lead our internal AI and automation strategy. We teach AI literacy to youth across Canada, and we intend to be a living example of what a thoughtfully AI-enabled organization looks like. You'll own how we put AI to work internally: finding the manual, repetitive work that eats our teams' time, building or piloting solutions (hands-on where you can), getting people to actually use them, and showing the hours and capacity we win back. We're a lean charity with big ambitions - every hour you free up is an hour redirected toward students, educators, and communities.
- Extend the CEO's reach. Prepare decisions, lead special projects, and represent the CEO in internal forums so momentum never depends on one person's calendar.
- Sharpen how we operate. Leadership meetings, goal-setting and KPI tracking, reporting,



and the discipline of clear decisions with clear owners - you'll design and run the systems that keep everyone rowing in the same direction.

What success looks like in year one

- Cross-team initiatives finish on schedule with clear ownership at every step.
- The organization measurably reclaims time through the automation and AI practices you've put in place.
- Leadership decisions get made faster, stick, and reach the people they affect.
- The CEO spends most of their time on external priorities, confident the internal engine runs without them.

Who you are

- 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.

Why join us

- Mission with scale. Your work directly expands how many young people — especially those from underserved communities — get the digital and AI skills to shape their future. Operations here isn't back-office; it's the engine of the mission.
- Practice what we teach. Help a leading AI-education charity become the proof point for how nonprofits can responsibly harness AI — a story you'll help write, not just support.
- A true thought partnership with the CEO, with real access, real trust, and a seat at the leadership table.
- Rare scope. Organization-wide influence from day one, at the intersection of education, technology, and social impact — alongside global partners and a community of educators and youth across Canada and beyond.

Benefits

- 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.
- 20 jours de vacances annuelles (incluant 5 jours en décembre pendant la fermeture des bureaux).
- Des avantages sociaux collectifs, notamment une assurance médicale, une assurance de congés parentaux, une assurance dentaire, et un complément de REER.
- Travailler à domicile et un horaire adaptable de 35 heures par semaine.
- 10 jours personnels/bien-être par année.
- Des opportunités de développement et de formation continue.

EEO Statement

Digital Moment is proud to be an equal opportunity employer who champions collaboration, innovation, and diversity of thought.

We pride ourselves on being a truly collaborative, innovative and diverse team. We celebrate the big - and small - wins. We laugh often and love to build connections. We support and help each other learn and grow. We are really good at what we do and we care a lot about doing it.

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