Top Chief Of Staff Jobs in Toronto

Chief of Staff to the CEO responsible for executive alignment, OKRs, leadership cadence, board governance, strategic initiatives, M&A coordination, and CEO communications. The role tracks commitments, drives cross-functional decisions, manages operating rhythms, supports planning cycles, and leads a small Business Operations team. Success requires strong influence without authority, strategic and financial fluency, operational rigor, discretion, and experience in scaling B2B SaaS, fintech, or payments organizations.

Partners with a senior operations executive to lead strategic growth projects, pricing and service experiments, sales funnel analysis, operating scorecards, goal reviews, financial planning, P&L reporting, market research, and executive communications. The role drives organizational cadence, tracks performance, identifies growth opportunities, and supports decision-making through clear analysis and board-ready reporting.

Chief of Staff supporting the Chief AI Officer by managing organizational planning, operating rhythms, budgets, headcount, business reviews, cross-functional dependencies, and strategic initiatives. The role coordinates research, modeling, product, delivery, security, finance, and other teams to ensure priorities are aligned and programs ship effectively. It also leads special projects, facilitates executive communication, resolves ownership and trade-off issues, and represents the AI organization in high-stakes discussions.

Serve as a strategic partner to the CRO and GTM leadership team by translating company strategy into priorities, operating plans, and measurable outcomes. Lead executive operating mechanisms, business reviews, QBRs, strategic planning, and complex cross-functional initiatives. Improve GTM effectiveness, align senior stakeholders, resolve organizational barriers, synthesize business insights, and build scalable operating systems across Sales, Marketing, Customer Success, Channel, and Revenue Operations.

The Chief of Staff and EOS Integrator partners with the CEO to translate strategy into company priorities, quarterly Rocks, scorecards, and accountable execution. The role aligns customers, partners, growth, technology, product, and operations; leads weekly leadership meetings; manages customer and partner commitments; supports product delivery and market expansion; and embeds AI agents into company workflows. The position begins fractionally with potential to become full time and is compensated through equity.

Supports Audit function strategy, performance management, financial coordination, leadership governance, executive communications, engagement activities, and strategic initiatives. The role develops KPI reporting and scorecards, coordinates leadership routines and governance forums, prepares executive materials, tracks strategic commitments, facilitates cross-functional collaboration, and supports town halls, offsites, and organizational effectiveness projects.

Partner with the Head of Talent to scale a global Talent organization. Translate strategy into execution, lead high-visibility talent initiatives, embed with teams needing leadership or expertise, improve cross-functional processes, and use hiring data, tools, and AI to strengthen recruiting and talent operations.

Two-year executive leadership program partnering with operating leaders, CEOs, and functional teams across vertical software companies. Own cross-functional value-creation initiatives spanning go-to-market, sales, marketing, pricing, customer success, finance, M&A integration, and business operations. Support executive decision-making, implement operating improvements, and help newly acquired companies establish priorities and operating rhythms. High performers may advance into CEO, C-suite, or headquarters leadership roles.

Deputy to the Chief Engineer responsible for leading engineering personnel, planning and executing maintenance and repairs, managing spares and fuel operations, ensuring environmental compliance, supporting safety investigations, and maintaining the shipboard management system and risk assessments.

Chief of Staff serving as a strategic advisor and organizational integrator for WES Canada’s Managing Director and leadership team. Responsibilities include coordinating executive priorities, board governance, strategic planning, dashboards, budgets, communications, cross-functional initiatives, and organizational reporting. The role manages high-priority projects, supports decision-making, monitors execution, builds stakeholder relationships, and supervises administrative staff in a complex, matrixed nonprofit environment.

Chief of Staff to the CEO responsible for driving company priorities, building the organization’s operating cadence, managing KPI reporting, leading cross-functional special projects, and increasing executive leverage. The role requires turning ambiguous problems into measurable plans, coordinating leaders and external partners, deploying AI effectively across operations, and improving organizational efficiency in a high-growth B2B SaaS environment.

The Chief of Staff will lead diverse initiatives, drive AI transformation, manage client relationships, and operate autonomously in a fast-paced environment.

Work directly with founders to drive multi-GW energy projects end-to-end: deliver construction and procurement milestones, lead special projects, support large-scale project and equity financing, hire across levels, and resolve urgent operational issues on-site.

Partner with the CEO and CTO to turn discussions into durable decisions, run executive cadence, validate analyses (including AI-assisted work), own priority cross-functional initiatives end-to-end, manage risk intake, and ensure commitments are executed with clear owners and measurable outcomes.

The Chief of Staff/Business Operations Manager will drive strategic initiatives, optimize processes, and collaborate with executives to achieve company objectives.

Hands-on generalist operator who builds and owns legal, compliance (HIPAA), HR, payroll, accounting, vendor management, and day-to-day operations. Manages outside counsel, contract lifecycle, audits/certifications (e.g., SOC 2), onboarding/offboarding, payroll/AP/AR, and operational processes to scale a healthcare startup.

The Chief of Staff will partner with the Managing Director of AI, leading AI transformation initiatives, designing automated processes, and ensuring successful client engagement and organizational rollouts.

Partner with the CEO to create operational clarity and accountability across a fast-growing AI startup. Own vendor/contract management, finance/ops logistics, recruiting-process machinery, cross-team coordination, leadership operating rhythms, and high-priority special projects. Convert founder intuition into scalable processes while retaining agility.

Lead operational rhythms and client delivery, focusing on AI solutions. Collaborate with executives and manage multi-stakeholder projects for positive outcomes.

The Chief of Staff will lead operational projects, ensuring delivery of AI solutions, managing client relations, and coordinating cross-functional efforts for success.