See All Jobs Executive Assistant Private Equity, PropTech, Real Estate, SaaS (Software as a Service), Software, Technology Type Full-Time Location(s) Kingston, Kingston, Canada Remote Compensation CAD $30,000 - CAD $35,000 Annually Share This Job Full-Time

Kingston, Kingston, Canada

Remote Important Location Requirement: This is a remote position; however, candidates must be located in the same country, city, or region where the job is posted. The successful candidate must be available to attend a local office, meeting, training session, or company event if requested. Please only apply if you are based in the location listed on this job posting.

Remote does not mean the position is open worldwide. EST Hours Required Support a Founder Who Operates at High Speed The Rothenbury Group owns and operates businesses across real estate, technology, property management, brokerage, leasing, maintenance, staffing, media, and other technology-enabled service companies. We’re looking for an experienced Executive Assistant to work directly with the CEO.

This role is designed for someone who thrives in fast-moving environments where priorities change quickly, confidentiality is critical, and every day looks different. You’ll help keep the CEO organized, informed, prepared, and focused by managing schedules, meetings, communication, follow-up, and day-to-day execution across multiple companies and ongoing initiatives. If you’re someone who enjoys bringing structure to complexity, anticipating problems before they happen, and making senior executives more productive, we’d like to hear from you.

Our Hiring Process

Every application is reviewed by our recruiting team. If your experience aligns with what we’re looking for, you’ll receive an email within 24 to 48 hours of applying with a link to complete a pre-recorded online interview.



The interview helps us better understand your executive support experience, organization, communication style, AI experience, judgment, professionalism, and ability to thrive in a fast-moving executive workplace.

Selected candidates will then continue through the next stage of the interview process. What You’ll Be Doing Your Responsibilities Will Include Managing the CEO’s calendar, meetings, and daily priorities

Coordinating schedules across multiple companies and stakeholders

Preparing meeting agendas, recording detailed notes, and tracking action items

Following up with employees, executives, contractors, vendors, and external partners to ensure commitments are completed

Preparing reports, summaries, presentations, documents, and executive communications

Managing confidential business information with professionalism and discretion

Coordinating travel, logistics, and scheduling when required

Helping organize projects, deadlines, priorities, and executive workflows

Supporting multiple business initiatives while maintaining exceptional attention to detail

Using AI tools to improve productivity, organization, research, documentation, communication, and executive efficiency Who We’re Looking For The Ideal Candidate Will Have 5+ years supporting a CEO, Founder, Owner, or senior executive

Experience supporting multiple executives, companies, departments, or major initiatives simultaneously

Outstanding organizational and time-management skills





Excellent written and verbal communication

Strong judgment, professionalism, and discretion The confidence to professionally follow up with senior leaders and hold people accountable for commitments The ability to remain calm under pressure while managing changing priorities

Advanced experience using AI tools such as ChatGPT, Claude, or similar platforms to improve workflows, research, documentation, summaries, and executive productivity A Bachelor’s degree or equivalent professional experience is preferred Technology Requirements This Is a Fully Remote Role. You’ll Need Dual-monitor setup

Computer with 16 GB RAM minimum

Reliable internet connection (100 Mbps or faster)

Webcam

Noise-cancelling headset

Professional, quiet workspace during Eastern Time business hours What Success Looks Like The right person doesn’t wait to be asked. They anticipate needs, stay one step ahead, protect the CEO’s time, and make sure priorities continue moving without constant reminders. They know how to manage competing priorities, communicate clearly, handle confidential information professionally, and remain composed when plans change unexpectedly.

Most importantly, they create clarity, consistency, and reliability in an environment where speed and execution matter. Why Join the Rothenbury Group? Work directly with the CEO across multiple growing companies

Exposure to technology, AI, operations, real estate, media, staffing, and business strategy

Opportunity to support meaningful projects across a diverse group of businesses

Competitive compensation based on experience

Long-term growth within a fast-moving, technology-driven organization The opportunity to become a trusted member of the CEO’s inner circle See all open roles

📌 Executive Assistant (Kingston)
🏢 Rothenbury Group
📍 Kingston