Executive Assistant

About CloudNorth Systems

CloudNorth Systems is a managed IT and cloud services provider specializing in supporting small to mid-sized Canadian businesses by acting as their outsourced IT department. The company offers managed services such as IT support, proactive monitoring, helpdesk assistance, system patching, cybersecurity, and cloud migration solutions. Their goal is to deliver enterprise-level technology reliability while maintaining affordable pricing tailored to each client’s unique needs, fostering long-term partnerships for ongoing operational excellence.

Role Overview

We are seeking a highly organized Executive Assistant to join CloudNorth Systems in a full-time, hybrid capacity based in the Greater Toronto Area. This role requires providing comprehensive administrative support to senior leadership, including calendar management, scheduling meetings, coordinating travel arrangements, preparing and reconciling expense claims, and drafting correspondence. The assistant will also develop presentations, handle meeting materials, and facilitate internal and external communications. Additional responsibilities include maintaining confidential files, supporting office administrative tasks, overseeing meeting logistics and follow-ups, and serving as a liaison between executives, internal teams, and external partners.

Key Qualifications

• Demonstrated experience providing high-level executive administrative support, including expertise in managing calendars, organizing meetings, and planning travel.
• Proven ability to prepare and accurately reconcile expense reports and manage related documentation.
• Outstanding written and verbal communication skills, enabling effective interaction with executives, staff, and external contacts.
• Strong administrative competencies such as document management, data entry, filing, and maintaining an organized office environment.
• High degree of professionalism and discretion when handling sensitive and confidential information.
• Exceptional time management, prioritization, and multitasking skills, capable of thriving in a dynamic, fast-paced setting.
• Proficiency in productivity software including Microsoft 365 or equivalent office applications, calendar systems, and email platforms.
• Experience supporting senior or C-level executives is advantageous.
• Post-secondary education in business administration or related disciplines, or comparable professional experience.