Chief of Staff - Montreal, Canada

5+ years in operations, client services, program/project management, or strategic support roles with direct ownership of client-facing delivery. Demonstrated success leading multi-stakeholder projects end-to-end (scope, timelines, budgets, risk, and change management). AI fluency: understands common LLM-enabled use cases; can shape prompts/playbooks, evaluate quality at a basic level, and choose appropriate off-the-shelf tools or vendors. High proficiency with Google Workspace, Asana/Notion, Slack. Comfort with modern web and content tools. Experience preparing polished executive documents and presentations. Bonus: familiarity with no/low-code automation, knowledge bases, and responsible AI considerations.

Partner with executive team to translate priorities into plans and outcomes. Maintain focus and accountability on deliverables, surfacing risks. Convert complex AI concepts into clear options with trade-offs. Produce executive materials for alignment and decisions. Own end-to-end delivery on client engagements involving AI-enabled solutions. Run discovery to surface use cases and translate findings into scopes. Coordinate solution build-outs with internal and external partners. Set evaluation routines for quality, safety, and user acceptance testing. Lead client check-ins, demo readiness, and present options. Track budget and scope, manage subcontractors, and ensure on-budget delivery. Create guides, FAQs, and training for client team adoption. Design and improve the operating system for work. Manage staffing and subcontractor contributions. Establish dashboards for delivery health and run meeting cadences. Prepare agendas, briefings, and executive presentations. Provide reporting on progress, risks, and decisions.