Executive Assistant to Chief Executive Officer
About the role
Executive Assistant & Law Clerk
📍 Whitby, ON (On-site / Hybrid)
💰 $65,000–$75,000 per year (based on experience)
💼 Full-time, Permanent
Make an Impact at the Executive Level
At Cottage Dream Vacations (CDV) , we help Canadians build wealth through real estate investing and building luxury resorts across Canada — and we’re looking for a proactive, detail-driven Executive Assistant & Law Clerk to support our CEO and leadership team.
This is a dynamic, fast-paced role for someone who thrives on organization, precision, and the satisfaction of keeping complex operations running smoothly. You’ll have a front-row seat to the strategic decisions that drive our growth, while managing critical legal, real estate, and executive initiatives.
What You’ll Be Doing
Executive Support
- Manage complex calendars, prioritize appointments, and coordinate meetings and travel.
- Prepare the CEO for meetings with agendas, briefings, and key documents.
- Handle confidential communications with professionalism and discretion.
- Act as a trusted liaison between the CEO and internal/external stakeholders.
Legal & Real Estate Administrative Support
- Draft, organize, and manage confidential real estate documents, agreements, and contracts.
- Support corporate governance tasks — meeting minutes, resolutions, and corporate records.
- Conduct due diligence and manage both digital and physical filing systems.
- Coordinate closings and liaise with legal counsel, agents, and municipalities.
- Track key legal dates and ensure compliance with deadlines.
Project & Information Management
- Support the execution of strategic business projects and operational initiatives.
- Track progress, manage follow-ups, and keep workflows aligned with company goals.
What You Bring
- Diploma or Certificate in Law Clerk Studies (or equivalent legal training/experience).
- 3–5 years in an Executive Assistant or Law Clerk role supporting senior leadership.
- Experience in real estate law — purchase/sale agreements, land registry, and closings.
- Exceptional attention to detail , time management, and organizational skills.
- Strong written and verbal communication with a professional, polished tone.
- Tech-savvy with Google Workspace , Microsoft Office , and digital document systems.
- High emotional intelligence, sound judgment, and absolute confidentiality.
Why You’ll Love Working Here
✨ Make a direct impact on key projects and business outcomes.
🚀 Grow within a fast-evolving, entrepreneurial company.
🤝 Work alongside an ambitious, collaborative leadership team.
💰 Earn a competitive salary of $65,000–$75,000 with room to grow.
Executive Assistant to Chief Executive Officer
About the role
Executive Assistant & Law Clerk
📍 Whitby, ON (On-site / Hybrid)
💰 $65,000–$75,000 per year (based on experience)
💼 Full-time, Permanent
Make an Impact at the Executive Level
At Cottage Dream Vacations (CDV) , we help Canadians build wealth through real estate investing and building luxury resorts across Canada — and we’re looking for a proactive, detail-driven Executive Assistant & Law Clerk to support our CEO and leadership team.
This is a dynamic, fast-paced role for someone who thrives on organization, precision, and the satisfaction of keeping complex operations running smoothly. You’ll have a front-row seat to the strategic decisions that drive our growth, while managing critical legal, real estate, and executive initiatives.
What You’ll Be Doing
Executive Support
- Manage complex calendars, prioritize appointments, and coordinate meetings and travel.
- Prepare the CEO for meetings with agendas, briefings, and key documents.
- Handle confidential communications with professionalism and discretion.
- Act as a trusted liaison between the CEO and internal/external stakeholders.
Legal & Real Estate Administrative Support
- Draft, organize, and manage confidential real estate documents, agreements, and contracts.
- Support corporate governance tasks — meeting minutes, resolutions, and corporate records.
- Conduct due diligence and manage both digital and physical filing systems.
- Coordinate closings and liaise with legal counsel, agents, and municipalities.
- Track key legal dates and ensure compliance with deadlines.
Project & Information Management
- Support the execution of strategic business projects and operational initiatives.
- Track progress, manage follow-ups, and keep workflows aligned with company goals.
What You Bring
- Diploma or Certificate in Law Clerk Studies (or equivalent legal training/experience).
- 3–5 years in an Executive Assistant or Law Clerk role supporting senior leadership.
- Experience in real estate law — purchase/sale agreements, land registry, and closings.
- Exceptional attention to detail , time management, and organizational skills.
- Strong written and verbal communication with a professional, polished tone.
- Tech-savvy with Google Workspace , Microsoft Office , and digital document systems.
- High emotional intelligence, sound judgment, and absolute confidentiality.
Why You’ll Love Working Here
✨ Make a direct impact on key projects and business outcomes.
🚀 Grow within a fast-evolving, entrepreneurial company.
🤝 Work alongside an ambitious, collaborative leadership team.
💰 Earn a competitive salary of $65,000–$75,000 with room to grow.