Assistant Executive Director jobs

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 administration and communication on behalf of the CEO and the company. From time to time, you may provide overflow support for the Chief Revenue Officer and the technical co-founder with travel, expenses and external meetings.

• Review materials with a sharp eye. Much of the CEO's material for the board, investors and the company is AI-generated and can contain errors or hallucinations. You'll oversee its accuracy, both through agents and automations you build and through careful manual review.

• Plan resilient, efficient travel. You'll plan multi-city trips across time zones, including meetings, breakfasts and dinners, restaurant reservations and ground logistics. When something goes wrong, you'll get it back on track and smooth things over with the people affected.

• Support events in Markham–Unionville and on the road. You'll organize networking dinners and VIP gatherings at our Markham–Unionville sales and events office and in the San Francisco Bay Area, at restaurants, event spaces and the CEO's home. That covers catering, guest logistics, guest bios, profiles and analyses, and follow-up. Early on, you'll also oversee the office's renovation, keeping contractors, schedules, paperwork and approvals moving.

• Handle personal logistics. As a partial personal assistant, you'll take home workloads off the CEO's plate so they can spend more time on the company: supporting family logistics and needs, and coordinating personal travel, travel documents and service providers. The CEO typically works while on family vacations, so you'll organize activities and logistics that let that work flow.

• Find, vet and select vendors. For personal and professional needs, you'll screen vendors, check references and credentials, run requests for proposals (RFPs), compare bids and recommend the best fit, using AI to speed up research and comparison while making the final call yourself.

• Manage relationships and follow-up. You'll maintain the CEO's contacts, draft messages for the CEO's review, track follow-ups and handle gifts and thank-yous.

• Be a true partner. You'll keep in touch through quick calls and texts throughout the day, and offer candid input on priorities and how the CEO's time is spent.

What you bring

• At least 3 to 5 years of experience as an executive assistant or personal assistant to a CEO, founder or other high-profile principal.

• Precision and responsiveness by text, phone and email, keeping pace with a dynamic, fast-moving CEO and culture.

• Exceptional attention to detail. You catch the errors others miss, in a schedule, the business terms of a contract or a board slide.

• Exceptional presence: warm, gracious and polished on the phone, in writing and in person.

• Excellent judgment, absolute discretion and trustworthiness, including managing need-to-know information across compartmentalized projects and keeping complex information-sharing rules straight.

• Political neutrality at work. You're free to hold your own political views outside work; inside the company, we stay politically neutral and support governments in protecting their citizens. If you choose to make your affiliation with the company public, apply a simple test: if an adversary put any of your public statements on the front page of a major newspaper, would you, the company, our partners or our customers be uncomfortable?

• Ease with a dynamic founder-CEO. We work toward quarterly and twice-yearly targets, and within those priorities, days and weeks can change quickly. Your job is to make that change flow smoothly.

• Comfort with AI tools, or eagerness to learn them quickly.

• Ability to travel once or twice a quarter and pass detailed background checks.

• Legally eligible to work in Canada, living in Toronto or the Greater Toronto Area, and able to attend in-person events in Markham–Unionville.

How we evaluate: IQ, EQ, JQ and PQ

• IQ (problem-solving): you turn complex, moving logistics into a workable plan and find good options under tight constraints.

• EQ (reading people): you sense what someone needs and adjust your tone so they feel respected, whether inviting, declining or apologizing.

• JQ (decision quality): you make sound calls with incomplete information, including what's need-to-know and what to decide yourself versus bring to the CEO.

• PQ (navigating power): you understand rank, protocol and influence, use them to get the right people in the room, and recognize when someone is using them on you.

Nice to have

• A background in technology, executive operations, investment banking, private equity, management consulting, private service or hospitality.

• Graphic design experience. The CEO was previously an interaction designer and values attention to detail and visual layout, particularly on slides.

• Experience with technical platforms such as Jira, Confluence, GitHub and AI tooling (helpful, not required).

• Experience living or working in more than one country.

Compensation: C

135,000–C180,000 annual cash compensation, depending on capabilities.

We use AI tools to help screen and assess applications. A person on our team reviews every application before any hiring decision is made.

This posting is for an existing vacancy.

Pay: $135,000.00-$180,000.00 per year

Work Location: Remote