Chief of Staff Montreal Canada at Oliver James — NeverHard

About The Opportunity Our client, a leading Canadian insurance brokerage, is seeking a Chief of Staff to serve as a strategic partner to the CEO and executive leadership team. Chief of Staff Location: Canada (Hybrid) This highly visible position will play a critical role in driving the firm’s strategic priorities, supporting executive decision-making, and ensuring alignment across key business initiatives. The successful candidate will operate at the center of the organization, helping transform strategy into execution while working closely with senior leaders across all areas of the business. This is a unique opportunity for an ambitious, intellectually curious, and commercially minded professional who thrives in fast-paced environments and enjoys solving complex business challenges. Position Overview The Chief of Staff will act as an extension of the CEO, helping manage strategic initiatives, coordinate cross-functional projects, and drive accountability across the organization. The role requires a combination of strategic thinking, operational excellence, executive presence, and the ability to influence stakeholders at all levels of the business. This individual will have exposure to board-level discussions, growth initiatives, operational priorities, acquisitions, talent strategies, and enterprise-wide transformation projects. Key Responsibilities Executive Partnership Serve as a trusted advisor and thought partner to the CEO. Support executive decision-making through research, analysis, and strategic recommendations. Prepare briefing materials, presentations, and executive communications. Manage and prioritize key strategic initiatives on behalf of the CEO. Strategic Planning & Execution Drive execution of enterprise-wide strategic priorities. Monitor progress against business objectives and key performance indicators. Coordinate initiatives across multiple business units and functions. Identify risks, bottlenecks, and opportunities impacting organizational performance. Cross-Functional Leadership Partner with leaders across Broking, Employee Benefits, Operations, Finance, Technology, Claims, and Corporate Development. Facilitate communication and alignment among executive stakeholders. Lead special projects and business transformation initiatives. Operational Excellence Establish governance frameworks and reporting structures. Develop executive dashboards and performance reporting. Improve organizational processes and operating efficiencies. Ensure accountability for key deliverables across the leadership team. Mergers, Acquisitions & Growth Initiatives Support strategic growth projects, including acquisitions, integrations, and market expansion initiatives. Assist with due diligence, executive presentations, and integration planning. Coordinate internal stakeholders throughout transaction and implementation processes. Qualifications Bachelor’s degree required; MBA or advanced degree preferred. 5-10+ years of experience in strategy, consulting, operations, finance, corporate development, insurance, or a related field. Experience working with senior executives and leadership teams. Strong analytical, problem-solving, and project management capabilities. Exceptional communication and presentation skills. Ability to manage multiple priorities in a fast-paced environment. High degree of professionalism, discretion, and executive maturity. Preferred Backgrounds Candidates may come from: Insurance Brokerage Management Consulting Corporate Strategy Business Operations Corporate Development Financial Services Professional Services Experience within insurance, risk management, employee benefits, or financial services is highly desirable but not required. Success Profile The Ideal Candidate Will Demonstrate Executive presence and confidence Strategic and commercial thinking Intellectual curiosity Strong organizational skills Ability to influence without authority High attention to detail Bias toward action and execution Strong relationship-building capabilities Why Join? Direct partnership with the CEO and executive leadership team. Exposure to enterprise-level decision-making. Opportunity to influence the future direction of a leading Canadian brokerage. High visibility across the organization. Significant career development and leadership opportunities. Dynamic, entrepreneurial, and growth-oriented environment. #J-18808-Ljbffr