Job Description

About the Role

We are seeking a highly experienced and detail-oriented Executive Assistant to provide direct support to the Chief Executive Officer (CEO), an entrepreneur overseeing multiple companies in the insurance industry. This role requires a professional who can balance corporate and personal responsibilities, operate effectively in a fast-paced environment, and adapt quickly to shifting priorities.





The successful candidate will act as a trusted partner to the CEO, ensuring that priorities are executed with precision, discretion, and proactive problem-solving.

Key Responsibilities

Provide comprehensive executive support, including calendar management, email correspondence, meeting coordination, and follow-ups. Assist with both corporate and personal tasks, including travel arrangements, errands, and event coordination. Support operations across multiple companies, ensuring seamless organization and execution. Serve as a key point of contact and gatekeeper, exercising judgment to prioritize requests and protect the CEO's time. Prepare and manage documentation, reports, presentations, and communications with accuracy and professionalism. Anticipate the needs of the CEO and proactively resolve scheduling, operational, and logistical challenges. Represent the CEO with discretion and professionalism in all interactions. Maintain confidentiality and handle sensitive information with the highest level of trust. Adapt to varying work hours, including occasional evenings and weekends, based on business needs. Utilize and adapt to productivity, communication, and project management tools as required.

Required Qualifications

Minimum of 5 years' experience as an Executive Assistant supporting senior executives. Insurance industry experience is considered an asset but not required. Advanced proficiency in Microsoft Office Suite (Word, Excel, Outlook, PowerPoint) Strong organizational skills with exceptional attention to detail. Ability to multitask and manage competing priorities under tight deadlines. Excellent written and verbal communication skills. High degree of professionalism, discretion, and reliability. Proactive and resourceful, with the ability to anticipate needs and act independently. Adaptable to shifting priorities and comfortable working in a dynamic, entrepreneurial environment. Must be based in Calgary (preferably South Calgary) and able to work in a hybrid arrangement, with 1-2 days per week in the office as required.

Why Join

This is a unique opportunity to work directly with a CEO/entrepreneur and gain exposure to diverse industries and business initiatives. The role offers flexibility through a hybrid work arrangement and the chance to make a meaningful impact in both corporate and personal spheres.

To Apply

Please submit your resume and a brief cover letter outlining your relevant experience and interest in this opportunity. We thank all applicants for their interest; only those selected for an interview will be contacted.