Job Summary: The Strategic Executive Assistant serves as a trusted administrative and strategic partner to the President and Vice President (Visionary and Integrator). This role exists to enable both leaders to focus fully on strategic priorities by removing friction, managing daily workflows, and ensuring seamless coordination of executive operations. Responsibilities span from managing calendars and communications to advising on high-impact programs like Temporary Foreign Worker planning. This individual acts as a gatekeeper, problem-solver, and liaison—driving alignment, accountability, and execution across the leadership team. The ideal candidate is humble, driven, and solutions-oriented, exemplifying discretion, proactivity, and reliability. This person is not only detail-oriented and organized but also able to anticipate needs, communicate effectively, and help maintain organizational alignment with leadership priorities. The Strategic Executive Assistant will also assist in coordinating (Sensitive)family-related logistics, such as childcare arrangements, to support a healthy work-life balance for the President and Vice President ensuring their full focus on their leadership responsibilities.
This role requires an individual who exemplifies the company values of humble, driven, and solutions-oriented.
Humble – Employees that are team players and are respectful of others and the job at hand. Great team players lack excessive ego or concerns about status. Humble employees are quick to point out contributions of others and slow to seek attention of their own.
Driven – Employees who are motivated and focused on self improvement. Driven or hungry employees are always looking for more. More things to do, learn, and take responsibility for. They never have to be pushed by a manager to work harder because they are self-motivated and diligent.
Solutions Oriented – Employees who focus on solving, and preventing problems from occurring, not just identifying them. This is equal parts of problems with systems and processes and the common sense that an employee has about people. They are aware, act appropriately, ask good questions, and listen to understand.
Role and Accountability:

• Executive & Administrative Support
• Serve as the single point of contact and trusted gatekeeper for the President and Vice President (Visionary and Integrator), ensuring alignment on high-priority strategic and operational work.
• Act as a personal executive assistant to both the President (Visionary) and Vice President (Integrator), coordinating their calendars, appointments, and family-related obligations (e.g., school events, travel logistics) to ensure smooth daily operations and no scheduling conflicts.
• Monitor and coordinate communications across platforms (e.g., email, text, WhatsApp), triaging priorities and drafting correspondence on behalf of the President or Vice President when appropriate.
• Create and maintain a private communication channel (e.g., WhatsApp group) between the President and VP to ensure quick and effective decision-making.
• Prepare materials for leadership meetings, including agendas, decks, pre-read summaries, notes, and action follow-ups. (Ensure meeting rooms, boardrooms or offsite locations are confirmed and set up prior to the commencement of attendees arriving
• Organize and maintain confidential records, meeting notes, and company documents related to executive operations.
• Provide administrative oversight and reminders using Microsoft To-Do (or similar tools) for executive task tracking and accountability.
• Maintain trusted access and readiness to support executive priorities, including time-sensitive matters related to either professional or personal domains.
• Coordinate domestic and international travel for the President and VP, including booking, itinerary planning, expense tracking, and submission of expense reports.
• Manage and safeguard confidential executive-level data and documents.
• Support executive-level event coordination, including off-site meetings and special engagements.
• Strategic & Cross-Functional Alignment
• Help enforce and manage Rocks, Scorecard tracking, and EOS meeting rhythms, ensuring team alignment with executive priorities.
• Ensure follow-up and accountability on action items discussed during leadership, off-site, and strategic planning meetings.
• Collaborate with the Strategic Project Manager and Finance & Operations Support to maintain project alignment, communication, and continuity.
• Draft or amend job descriptions, accountability chart, policies, and procedures as requested by the Integrator, coordinating version control and communicating updates to leadership.
• Coordinate and support executive reporting dashboards for KPIs, Scorecards, and quarterly Rock reviews.
• Maintain alignment of leadership initiatives with the broader company accountability chart and organizational priorities.
• Identify and recommend opportunities to improve communication flow and executive support processes.
• Program & Policy Oversight (TFW Advisory)
• Provide high-level advisory support to the leadership team on TFW and labour planning issues, ensuring that critical components (e.g., LMIA timelines, i2i communications, housing, inspections) are being managed effectively—without executing day-to-day tasks.
• Review housing plans, headcount plans, and labour projections to provide informed recommendations prior to leadership approvals.
• Identify risks or gaps in compliance or coordination and bring them forward proactively with solutions in mind.
• Offer guidance on key legislative or program changes affecting the TFW portfolio and assist other departments in ensuring readiness and alignment.
• Monitor weekly labour hours to ensure minimum thresholds are being met. Where outliers are identified—either significantly above or below expectations—follow up with the responsible parties to gather justification and drive transparency and accountability in scheduling practices.
• Continuity & Coverage
• Act as a backup to the Strategic Project Manager and Finance & Operations Support during absences, ensuring continuity of executive-level coordination and project tracking.
• Support short-term executive needs during periods of intensive planning or absence, ensuring continuity in communication and decision-making.
• Maintain key process documentation and SOPs to ensure continuity of knowledge and decision-making protocols during leadership transitions or absences.
• Confidentiality & Ethics
• Maintain strict confidentiality and handle sensitive information with the highest level of integrity and professionalism.
• Uphold ethical standards in all communications and activities, building trust and credibility with the leadership team.
• Crisis & Emergency Support
• Provide responsive support during urgent situations or crises, helping to coordinate rapid communication and problem resolution to minimize disruption.
• Execute daily responsibilities to meet departmental goals while adhering to company values ( Humble, Driven, Solutions - Orientated).
• Provide feedback and suggestions to improve processes within the scope of the role.
• Attend relevant department and company-wide meetings, including Level 10 meetings, contributing to organizational alignment and effectiveness.
• Collaborate cross-functionally to address challenges, develop solutions, and align strategies with company goals.
• Utilize Microsoft To-Do (or similar) for task tracking and reminders, ensuring productivity and accountability.
• Perform other duties as assigned.

Knowledge, Skills and Abilities:

• Proven experience supporting C-suite or senior leadership as an Executive Assistant, Strategic Coordinator, Chief of Staff, or high-level Administrative Advisor.
• Excellent organizational and time-management skills, with an innate ability to prioritize and balance multiple workflows.
• Strong written and verbal communication skills with a high degree of discretion and emotional intelligence.
• Proficiency in Microsoft Office Suite (Outlook, Word, Excel, PowerPoint) and digital productivity tools (Microsoft To-Do, OneNote, Loop, or similar).
• Ability to work independently and proactively, anticipate needs, and solve problems with a strategic lens.
• Knowledge of the Temporary Foreign Worker program is a strong asset but not required for execution.
• Experience or knowledge of HR and legal documentation processes is an asset.
• Familiarity with EOS (Entrepreneurial Operating System) or similar business operating systems is preferred.
• Demonstrated discretion and capability to manage a blend of professional and personal executive responsibilities, including sensitive or family-related logistics.
• Strong ethical judgement and ability to handle confidential information appropriately
• Skilled in managing urgent or crisis communications and coordinating quick responses.

Education and Experience:

• Post-secondary education in Business Administration, Office Management, Human Resources, or related field preferred.
• Additional coursework or certifications in executive support, HR, legal studies, or operations management is an asset.
• 3–5 years of experience in a senior-level administrative, operational, or executive support role.
• Demonstrated ability to work in a fast-paced, dynamic environment requiring confidentiality, multitasking, and judgment.

In accordance with the Ontario Human rights Code and the Accessibility for Ontarians with Disabilities Act, The Company is an equal opportunity employer who is committed to providing an inclusive and barrier free recruitment and selection process. Applicants should advise Human Resources if they require any type of accommodation during the recruitment process.
Salary $55,000 - $65,000 annually

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