Executive Assistant to Chief Executive Officer

Executive Assistant & Law Clerk📍 Whitby, ON (On-site / Hybrid) 💰 $65,000–$75,000 per year (based on experience) 💼 Full-time, PermanentMake an Impact at the Executive LevelAt 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 DoingExecutive SupportManage 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 SupportDraft, 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 ManagementSupport the execution of strategic business projects and operational initiatives.Track progress, manage follow-ups, and keep workflows aligned with company goals.What You BringDiploma 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.