Executive Assistant to a Founder-CEO

Executive Assistant to a Founder-CEO Remote (Toronto and Greater Toronto Area candidates only) | In-person events in Markham–Unionville once or twice a quarter | East Coast business hours | Travel once or twice a quarter About the role We're a Canadian-based company looking for an Executive Assistant to support a Canadian-US dual citizen founder and CEO of a profitable, growing, privately held technology company of about 120 staff, with contracts with global enterprises and critical infrastructure organizations around the world. The CEO keeps an intense travel schedule, spends personal time in either Toronto or the San Francisco Bay Area, and deeply integrates work and personal life. The identity of the company and the CEO will be shared under a non-disclosure agreement with candidates who pass the initial screens. The CEO works in cyber defence for critical infrastructure and national security, supporting the Canadian government, the US government, including the Department of War, and allies around the world. Working with public sector, military and industry leaders means absolute discretion is required, and precision and responsiveness are equally vital. You'll represent the CEO with grace, charm and discretion, and you'll shape how people experience the CEO and the company, from first contact through every interaction after. This is a remote role with no expectation of daily in-office work. It is open only to candidates living in Toronto and the Greater Toronto Area, because it includes in-person work supporting events at our sales and events office in the Markham–Unionville area, potentially once or twice a quarter, though this may vary over time. At the start of the role, you will oversee its renovation. Expect travel to the US or internationally once or twice a quarter, potentially to Ottawa, the San Francisco Bay Area, Washington, DC, or other venues. This is an AI-forward role. The company develops AI technologies for cyber defence, and supporting the CEO's adoption of AI is part of the job. You'll have your own fleet of AI agents for the work described here, with a budget for AI tools and colleagues who can help build automations. You'll be expected to use AI responsibly and keep up with the latest tools. Markets, AI technologies and roles at every company are changing quickly, and ours is growing fast, so parts of this role will change too. What endures is the human side: your judgment, relationships, presence, oversight and close partnership with the CEO, which only become more critical over time. What you'll do Partner in running executive operations for the CEO's priorities. In collaboration with the CEO, you'll expedite approvals, procurement and legal contracts across the executive leadership team and the company, and prepare materials for board and investor meetings. The role supports the CEO and their priorities. It is not a shared resource for the executive team, and requests from other executives should not compete with the CEO's priorities. Own the full calendar. This covers business meetings, conferences, speaking engagements, networking, and personal and family commitments, with a lot of multi-party scheduling, both external and internal. You'll reschedule and reprioritize as plans change, and guard against overbooking. Serve as the CEO's gracious emissary. The CEO receives many requests for advice, networking meetings, lunches and introductions. The best meetings are the ones both sides want, and you'll make those happen quickly. When the CEO wants to meet someone, you'll persist politely with their office until it's on the calendar. When a request doesn't fit the CEO's priorities, you'll decline or indefinitely postpone warmly so people still feel valued. No job too high, no job too low. You'll communicate with our board, investors, customers and advisory boards, including former three-star generals, and you'll also get a plane ticket refunded, chase down receipts and handle detailed adminis…

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