Olivia R.
Ea to the Founder & CEO Manager, Executive Support @Plusgrade
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WORK HISTORY
Ea to the Founder & CEO Manager, Executive Support @Plusgrade
Montreal, QC, CA
As Executive Assistant to the CEO and Manager of Executive Support, I serve as a strategic partner to the CEO, providing actionable insights to optimize their focus and drive key organizational initiatives. A major part of my role involves heading the Admin Function while leading and developing a dynamic team of Executive and Administrative Assistants. I champion the integration of AI-driven workflows across the team, enabling our team to automate repetitive tasks, streamline information flow, and elevate their impact so they can focus on higher-value, strategic support for the leadership team.In addition to executive support, I also manage Workplace and the company’s corporate travel program. This includes defining workplace and travel policies, supervising workplace and travel-related technology, negotiating with vendors, and overseeing budgets. I also lead the implementation of an AI-powered Agent within our travel ecosystem which is automating traveler assistance, enhancing risk management, and enabling real-time support for our global employees. We are currently working on developing a similar agent to enable the Workplace Team. These innovations ensure that our travel and Workplace operations remain efficient, scalable, and aligned with organizational needs.
EDUCATION
Dawson College
DEC, Photography
Concordia University
Bachelor of Fine Arts (BFA), Art History and Studio Arts
Concordia University
Diploma, Entrepreneurship
ABOUT OLIVIA R.
I am an AI-driven executive operations leader with 10+ years of experience supporting CEO/Founders and scaling Executive Support functions in fast-paced tech environments. I design intelligent workflows and build custom AI agents that enhance executive productivity, streamline operations, and reduce manual work—enabling leaders to focus on high-impact priorities.I have led major operational improvements including implementing EOS, designing executive meeting structures, developing integrated planning frameworks, and launching an AI-powered Travel & Expense Assistant used company-wide. My focus is on leveraging automation and data-informed systems to improve efficiency, clarity, and decision-making.As Executive Assistant to the CEO and Manager of Executive Support, I lead a high-performing team of Executive and Administrative Assistants while overseeing the company’s end-to-end corporate travel program. I champion AI adoption across Executive Support, Admin Operations, and Corporate Travel to ensure these functions are scalable, efficient, and continuously innovating.
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