Executive Assistant

OSL Retail Services Inc.; Mississauga; On-site; CAD 80,000 - 105,000; Full time

Benefits offered by this job

Competitive base salary

Generous vacation time

Comprehensive benefits

Retirement plan

Career growth

Job summary

OSL Retail Services Inc. in Mississauga seeks an experienced Executive Assistant to provide senior-level administrative support to the CEO/President of a Global Technology Company. The candidate must be dynamic, confidential, and adept at multitasking in a fast-paced environment.

Responsibilities include calendar management, travel coordination, event planning, document preparation, and managing confidential information. Some travel is required; discretion and professionalism are essential.

Qualifications

• 3+ years’ administrative experience supporting a Senior Executive in a fast-paced environment with multiple demands and an ever-changing schedule.
• Expert proficiency in Microsoft Suite including Adobe, Word, Excel, PowerPoint, Dropbox, Google.
• Discretion, tact, and loyalty; understands the importance of maintaining strict confidentiality.
• Polished, confident and professional manners as well as excellent communication and relationship management skills.

Responsibilities

• Prioritize incoming calls, meeting requests, conference calls, and communications.
• Research, book, and arrange travel for the CEO/President and family members, including flights, accommodations, and itineraries.
• Plan and execute business and social events, including venues, guest lists, catering, and entertainment.
• Execute on property management and financial settlements.
• Prepare proposals, letters, and client documents as required.
• Organize and manage charitable donations processing.
• Anticipate calendar, travel plans and expenses; optimize processes to drive results.

Skills

Discretion

Communication

Organisation

Multitasking

Education

Administrative experience

Tools

Microsoft Suite

Adobe

Word

Excel

PowerPoint

Dropbox

Google

Job description

Overview

The Executive Assistant will provide senior level executive administrative support to the CEO/President for a Global Technology Company as well as personal assistant to the CEO and family. The ideal candidate must be dynamic, confidential, and ability to multi-task.

The candidate must thrive in fast-paced environments, be able to manage through ambiguity and complexity, create and simplify processes, and simultaneously support and prioritize varying requirements/tasks impacting a growing organization. This role requires excellent communication and organizational skills and the ability to identify and eliminate bottlenecks, provide escalation management, anticipate, and make trade-offs and balance administrative and business needs versus operational constraints in alignment with the executive's preferences. Maturity, curiosity, creative problem solving, and the ability to work as part of a team are all essential for success in this role.

Location: Mississauga

Role Responsibilities:

• Prioritize incoming phone calls, meeting requests, conference calls, and communications.
• Research, book, and arrange travel for the CEO/President and family members, including transportation services, private aircraft or commercial travel, accommodations, meal and event reservations and preparation of comprehensive itineraries.
• Plan and execute business and social events including researching and booking venues, compiling guest lists, organizing catering and entertainment, and running the event.
• Execute on property management and financial settlements.
• Prepare proposals, letters, client documents as required.
• Organize and manage the processing of all charitable donations.
• Anticipate and organize calendar, travel plans and expenses.
• Proactively identify opportunities to optimize processes to drive business results.
• Assist in the creation of PowerPoint presentations.
• Utilize Microsoft Suite to create reports, analyze data, and report on trends.
• Research and carry out diverse and far-ranging personal requests and ensure ad hoc requests are completed in a timely manner.
• Running errands where required e.g. banking, shopping, delivery of personal correspondence.

Qualifications:

• 3+ years’ administrative experience supporting a Senior Executive in a fast-paced environment with multiple demands and an ever-changing schedule.
• Expert proficiency in Microsoft Suite including Adobe, Word, Excel, PowerPoint, Dropbox, Google.
• Discretion, tact, and loyalty; understands the importance of maintaining strict confidentiality.
• Polished, confident and professional manners as well as excellent communication and relationship management skills.
• Independent and resourceful self‑starter with the ability to manage multiple requests and meet deadlines.
• Proactive with the ability to solve problems, be creative, intuitive and anticipate needs.
• Strong team player with the ability to work independently.
• Demonstrated ability to perform well under pressure.
• Strong focus on accuracy and attention to detail.
• Flexible and adaptable in an environment with growing business needs.
• Ability to respond to out‑of‑hour requests according to the Executives’ needs as required.
• High energy and positive attitude.
• Some travel is required.

What’s in it for you:

• Competitive base salary: $80K-$105K plus bonus
• Generous time off: Start with 3 weeks of vacation, plus extra flex days to recharge.
• Comprehensive benefits package: Includes medical, dental, vision, & health spending account.
• Retirement support: Company-sponsored savings plan to help build your financial future
• Career growth: Ongoing training, development, and programs to help you advance.

The Interview Process:

• Step 1: If your profile is a match, we will invite you for a first conversation with the recruiter.
• Step 2: The next step is an in‑person interview with the Director Talent Acquisition.
• Step 3: The final step is an in‑person interview with the President/CEO.

We thank all interested applicants; however, only qualified candidates will be contacted. This position requires successful completion of a criminal background check.

Disclaimer: As part of our recruitment process, we utilize artificial intelligence (AI)-based tools to assist with certain stages, including initial resume screening and skills‑matching assessments. These tools are designed to help our hiring team identify candidates whose experience and qualifications align closely with the requirements of the role. Please note that all final hiring decisions are made by our recruitment team. The preceding job description has been designed to indicate the general nature and level of work performed by employees within this job. It is not designed to contain or be interpreted as a comprehensive inventory of all duties, responsibilities and qualifications required of employees assigned to this job. In compliance with Ontario’s Bill 190, we confirm that this posting represents a current existing vacancy within our organization.