At FIRST Insurance Funding of Canada (FIRST Canada), we are proud to promote a workplace that fosters growth and innovation. We employ a dedicated team of enthusiastic individuals who thrive in an entrepreneurial, fast-paced workplace. Our open concept and creative culture fosters team work and presents opportunities for growth within the organization. FIRST Canada is an affiliate of Wintrust, a financial services company with more than $66 billion in assets.

Join the FIRST Insurance Funding of Canada (FIRST Canada) team.

We are a multi-year Globe and Mail / Morneau Shapell Employee Recommended workplace with an award-winning culture.

We offer a flexible, hybrid-work model and our FIRST Flex program offers opportunity to work internationally.

We have a comprehensive benefit package including:

Health Benefits

Include Basic medical and dental coverage

We have a dedicated team of enthusiastic individuals who thrive in an entrepreneurial, fast-paced environment.

We support work / life balance and promote growth-from-within opportunities.

Why join this team?

- We have a culture that encourages an entrepreneurial spirit
- We offer multiple opportunities for development and upward mobility

Position Summary: The Executive Assistant will serve as a trusted partner to the CEO and COO, providing high-level administrative, organizational, and coordination support while helping ensure effective management of priorities, schedules, meetings, communications, and key business initiatives.

The Executive

Assistant will play an important role in maintaining strong connection to the employee experience and organizational culture. Through participation in key employee committees and culture initiatives, the EA will identify emerging themes and opportunities and appropriately share relevant feedback and insights with the CEO and COO. This role requires exceptional communication skills, sound judgement, discretion, and the ability to manage multiple priorities. The EA will be highly collaborative, demonstrate a high degree of professionalism and confidentiality, and be comfortable working with individuals at all levels of the organization.





Essential Duties and Responsibilities:

Executive Support

- Provide dedicated executive support to the CEO and COO, managing competing priorities, and ensuring both executives are appropriately supported.
- Manage complex calendars, schedule meetings, appointments, and events while ensuing effective prioritization of time and commitments.
- Coordinate travel arrangements, including itineraries, accommodations, transportation, and expense reporting.
- Screen, prioritize, and respond to correspondence on behalf of the CEO and COO, as appropriate.
- Prepare briefing materials, presentations, reports, agendas, and other documentation.
- Track action items, deadlines, and follow-up activities.
- Anticipate the needs of the CEO and COO and proactively identify opportunities to improve efficiency and effectiveness.

Meeting and Leadership Coordination
- Coordinate executive meetings, leadership team meetings, and other key stakeholder engagements.
- Prepare meeting agendas, materials, minutes, and follow-up documentation.
- Ensure timely distribution of meeting packages and support effective communication among participants.
- Coordinate executive events, business updates, and other organizational engagements.
- Support the coordination and follow-through of key organizational priorities and initiatives.

Employee Engagement and Organizational Culture
- Participate as a representative in key employee committees and culture initiatives which may include the Staff Engagement Committee and Health, Safety, and Wellness Committee.
- Represent the CEO and COO’s offices in a professional, approachable, and positive manner, contributing positively to FIRST Canada’s culture.
- Bring forward relevant observations, ideas,



and feedback gained through participation in organizational activities like the SEC and HSW committees, as appropriate, the help keep the CEO and COO connected to the broader organization.
- Support engagement and culture initiatives by helping coordinate activities, communications, and follow up.

Stakeholder Management
- Serve as a key point of contact for internal and external stakeholders interacting with the CEO and COO.
- Build and maintain strong working relationships across the organization and with external partners.
- Represent the CEO and COO professionally and appropriately in interactions with employees, leaders, clients, partners, and other stakeholders.
- Handle sensitive and confidential information with the highest level of discretion and professionalism.
- Administrative and Operational Support
- Manage expense reports, invoices, and budget tracking related to the CEO and COO offices.

Maintain accurate records, files, and documentation
- Support special projects, strategic initiatives, and organizational priorities as assigned.
- Assist in developing and improving administrative processes and procedures.
- Provide additional administrative and coordination support to the executive team as required.

Knowledge/ Skills/ Abilities Required:

- Excellent organizational, planning and time management skills and detail orientation
- Capacity to work independently and with a team on projects
- Must have excellent interpersonal communication (both written and oral), and telephone etiquette skills
- Customer focus in dealing with all levels of employees and visitors

Training / Education / Experience Qualifications:

- 5-7 years of experience supporting various management levels preferred
- Advanced skills with MS Office Suite
- Bachelor's degree or equivalent

Compensation: The estimated salary for this role is $59,000 - $77,000. Actual pay rate may vary based on several factors, such as a candidate’s qualifications, skills and experience.

AI Disclosure

No AI technology is used in the recruitment process

Vacancy Status

This position is a 12 Month Contract Opportunity

📌 Executive Assistant - FIFC (Toronto)
🏢 FIRST Insurance Funding of Canada
📍 Toronto