Position Summary

Reporting to the Chief Operating Officer (COO), the Executive Operations Lead serves as a trusted partner responsible for enhancing executive effectiveness, driving operational execution, and supporting a high-performing workplace experience across the organization. This role operates in a fast-paced, fluid, and evolving environment where priorities can shift quickly. The successful candidate will be comfortable navigating ambiguity, adapting to changing business needs, and managing multiple competing priorities with a high degree of ownership and limited direction.

They will bring structure to complexity, anticipate needs, exercise sound judgement, and remain focused on execution as priorities evolve.

The role combines executive support, project management, business analysis, workplace operations, and cross-functional coordination to help translate strategic priorities into measurable outcomes. Acting as an extension of the COO, the Executive Operations Lead manages critical information flow, develops executive-level presentations and communications, coordinates strategic initiatives, conducts research and analysis, oversees key workplace experience initiatives, and helps ensure organizational priorities continue to move forward.

The ideal candidate is highly organized, exceptionally discreet, analytically minded, resourceful, and capable of operating confidently with senior leaders. They thrive in dynamic environments, are comfortable shifting between priorities, and can move seamlessly between strategic initiatives and hands-on execution. They bring a proactive, solutions-oriented approach and a commitment to delivering both operational excellence and an exceptional employee experience.

Key Responsibilities

Executive Support & Communications (35%)

- Serve as a trusted and highly confidential partner to the COO.
- Manage the COO's priorities, ensuring alignment between strategic objectives, meetings, deliverables, and commitments.
- Develop, maintain, and continuously improve executive, leadership, board, and business presentations.
- Create professional PowerPoint presentations, briefing materials, reports, dashboards, and executive summaries for senior audiences.
- Draft, edit, and coordinate executive communications, correspondence, presentations, and meeting materials.
- Prepare meeting agendas, briefing notes, background information, and decision-support materials.
- Attend meetings as required, capture key actions, and ensure timely follow-up on commitments.
- Maintain strict confidentiality regarding business performance, organizational changes, employee matters, and strategic initiatives.

Project Management & Execution (20%)





- Coordinate and support cross-functional initiatives sponsored by the COO.
- Develop project plans, timelines, action trackers, and status updates for strategic priorities.
- Monitor progress against milestones and proactively identify risks, dependencies, and potential roadblocks.
- Facilitate project meetings and ensure accountability for deliverables across teams.
- Drive follow-up and execution of key action items resulting from leadership meetings and business reviews.
- Support organizational planning cycles and operational improvement initiatives.

Business Analysis & Research (20%)

- Conduct meaningful research on industry trends, competitors, market developments, operational practices, and business opportunities.
- Gather and assess information from multiple credible sources and synthesize findings into explicit, concise executive-level insights.
- Develop well-supported recommendations based on research and analysis to help inform executive decision-making.
- Prepare reports, business cases, presentations, and decision-support materials.
- Support the development and tracking of key business metrics and performance indicators.
- Translate complex information into clear, actionable summaries for leadership.
- Develop a strong understanding of the life insurance industry, distribution channels, products, regulatory environment, and business drivers.

Workplace Operations & Employee Experience (15%)

- Manage workplace planning initiatives, office enhancements, and facilities-related projects.
- Oversee the planning and execution of employee engagement activities, company events, leadership offsites, and workplace celebrations.
- Partner with HR and business leaders to deliver employee experience initiatives that support engagement and organizational culture.
- Oversee event budgets, logistics, communications, and execution for corporate and employee-facing events.
- Identify opportunities to improve workplace effectiveness, employee experience, and operational efficiency.

Stakeholder Coordination & Special Projects (10%)

- Serve as a liaison between the COO and leaders across the organization.
- Coordinate information gathering and collaboration across departments to support business initiatives.
- Build strong working relationships with stakeholders at all levels of the organization.




- Support executive and leadership team meetings, offsites, planning sessions, and strategic workshops.
- Lead or support special projects and business improvement initiatives as assigned.
- Ensure effective communication and alignment among stakeholders involved in key initiatives.

Qualifications

Education & Experience

- Bachelor's degree in Business Administration, Commerce, Finance, Communications, or a related field.
- 3+ years of experience in one or more of the following areas: executive support, project management, business operations, management consulting, or executive business partnering.
- Experience supporting senior executives or leadership teams is strongly preferred.
- Experience within financial services, insurance, or a regulated industry is considered an asset.
- Experience working in a start-up, growth-mode, or similarly fast-paced and evolving environment is considered a strong asset.

Skills & Competencies

- Exceptional discretion and ability to manage highly confidential information.
- Advanced Microsoft PowerPoint skills with demonstrated experience creating executive-level presentations.
- Strong business writing, communication, and presentation skills.
- Excellent analytical, research, problem-solving, and critical-thinking capabilities.
- Ability to conduct independent research, assess the credibility and relevance of information, and develop meaningful recommendations.
- Ability to synthesize large volumes of information into concise recommendations and action plans.
- Strong project coordination and organizational skills.
- Ability to influence and build relationships across functions without direct authority.
- Highly proactive, resourceful, and capable of working independently with limited direction.
- Strong attention to detail and commitment to quality.
- Advanced proficiency with Microsoft Office Suite, including PowerPoint, Excel, Word, and Outlook.
- Comfortable operating in a fast-paced and fluid environment where priorities can change quickly and multiple competing initiatives may need to be managed simultaneously.

Success in This Role

Successful candidates will become a trusted extension of the COO, consistently delivering high-quality work while navigating multiple, often changing priorities. They will be comfortable operating in a fluid environment, bringing structure and clarity to ambiguity, adapting quickly as business needs evolve, and ensuring critical initiatives move from concept to completion. They will create leverage for executive leadership by combining operational excellence, sound judgement, business acumen, resourcefulness, and exceptional execution.

📌 Executive Operations Lead (North York)
🏢 Greenstone Financial Services Canada
📍 North York