Executive Assistant to the CEO

the COOL companyKitchener, ON

About The Position

The COOL company is a global leader in AI-powered advertising technology, helping brands, agencies, and publishers simplify advertising and amplify performance. Powered by COOL AI, our intelligent platform unifies creative generation, media activation, optimization, and attribution into one continuously learning system. Instead of relying on fragmented tools and manual campaign management, COOL AI executes thousands of real-time micro-optimizations across search, social, display, video, and connected TV—helping customers launch faster, optimize continuously, and achieve stronger business outcomes. Our innovation and growth have earned industry-wide recognition, including being named a 7-time recipient of the Inc. 5000 list of America's Fastest-Growing Private Companies, a 2-time Deloitte Technology Fast 500 honoree, recognized on Crain's New York Fast 50, honored by the Digiday Media Awards for helping modernize digital media, and named one of Adweek's Top 10 Fastest Growing Solution Providers globally. We're building the future of advertising, where every signal becomes intelligence and every optimization drives performance. As we continue to grow globally, we're looking for curious, ambitious people who want to work with cutting-edge AI technology, solve complex challenges, and help redefine what's possible in modern advertising. We are seeking a highly organized and proactive Executive Assistant to support our CEO at a fast-growing AdTech company. The ideal candidate will have 5+ years of experience supporting an executive, with strong communication skills, excellent judgment, and the ability to manage multiple priorities in a fast-paced environment. This role requires someone who is detail-oriented, resourceful, and comfortable working across time zones while maintaining a high level of professionalism and confidentiality.

Requirements

  • 5+ years of experience as an Executive Assistant supporting an executive
  • Excellent written and verbal communication skills in English
  • Strong organizational and time-management skills
  • Ability to manage confidential information with discretion
  • Experience coordinating across international time zones
  • Proficiency with tools such as Google Workspace, Slack, Zoom, and calendar management systems
  • Strong attention to detail and ability to prioritize tasks effectively
  • Comfortable working in a fast-paced, startup environment

Nice To Haves

  • Experience working in technology or AdTech companies
  • Experience supporting senior leadership or C-level executives
  • Ability to manage multiple projects simultaneously

Responsibilities

  • Provide high-level administrative support to a senior executive
  • Manage complex calendars, schedule meetings, and coordinate across multiple time zones
  • Handle email management, prioritize communications, and draft professional correspondence
  • Coordinate internal and external meetings, including preparing agendas, documents, and follow-ups
  • Arrange domestic and international travel, including flights, accommodations, and itineraries
  • Support meeting preparation, take notes, and track action items
  • Liaise with internal teams, external partners, and stakeholders on behalf of the executive
  • Maintain organized records, documents, and reports
  • Assist with special projects, research, and operational tasks as required
  • Ensure smooth day-to-day operations by anticipating needs and proactively solving problems

Benefits

  • Opportunity to work closely with senior leadership
  • Exposure to a fast-growing global AdTech company
  • Dynamic and collaborative work environment
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