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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

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Description

- 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 environment.

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 quick-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