Executive Assistant

Come join our team!

High velocity, high intensity, high trust, high bar, high impact, and a will to win.

If those words resonate deeply with you, this could be your next career move. We're seeking someone who leads with humility, pursues audacious goals, and is motivated by meaningful impact on people and the world.

At Future Fit AI, our core mission is to help more people get to better jobs faster and cheaper, with a specific focus on those facing barriers to opportunity. Our work helps resolve the growing issue of economic inequality, ensuring that no one is left behind in the future of work. Our AI-powered platform brings efficiency and insight to workforce development, replacing outdated systems and unlocking human potential at scale.

Ready to make an impact? Apply today.

Important note:

Data shows that men typically apply when meeting 3/10 requirements, while women often wait until it's 10/10. We encourage you to apply if you see a strong (not necessarily perfect) fit.

We’re seeking a Executive Assistant to join our team. You will play a key role in helping our executive team run fast, and develop our organization.

A clarifying note on the shape of the role:
This role exists to extend the executive team’s bandwidth on the executional and logistical work. The split runs roughly sixty-forty, with sixty percent dedicated to executive support and forty percent to project and operations work. The person who fits is someone who wields the modern AI toolkit aggressively, with the result that the output looks like the work of two.

• Executive time and inboxes: Calendar architecture, prioritization, and gatekeeping, with the judgement to make tradeoff calls without checking first.
• Travel and the mechanics of the week: Booking, expenses, logistics, the small frictions that compound into lost hours if left untended.
• Pre-reads and preparation: Briefing documents for recurring meetings, so the CEO walks in already knowing what matters.
• Project work for the executive team: Offsites, executive travel, senior-hire candidate experience, event logistics, the operational scaffolding around important moments.
• Operations support: Cross-functional ops support during inflection points, in partnership with Strategy & Operations.
• Discretion: Comfort with sensitive information about people, finances, and strategy. The work involves knowing things one does not repeat.

• Five-plus years supporting a senior executive, ideally a founder or CEO at a venture-backed company, as an EA or as PA
• A demonstrated track record of taking on project work without dropping the core role.
• Comfort with ambiguity, confidential information, and a calendar that can change by the hour.
• Fluency with the modern AI toolkit. You use it daily, you have opinions about which tools earn their keep, and you are not waiting for permission to deploy them.
• Comfort with occasional flex outside standard business hours during periods of high intensity, and in-person availability on short notice when the work calls for it.

• Experience at a high-growth Series A through C startup.
• Event production or offsite logistics chops.
• Light project management discipline; you can build a simple tracker without one being handed to you.
• Background in workforce development, AI, or B2B SaaS.

Your alma mater isn’t our focus. Your grit, hunger, and drive are. If you learn continuously, tackle challenges head‑on, and know your strengths and gaps intimately—you’re our person.

We are open to candidates living anywhere in Canada or the US. For candidates living in Toronto, our office is conveniently located at 325 Front St West (a short walk from Union Station). You are welcome to come in on a hybrid schedule.

Although this role is remote, you may be expected to travel up to once per month.

The base salary range for this role is 130,000

USD-145,000

USD or the equivalent in CAD. This range reflects the varying levels of expertise and responsibilities that will be determined through the interview process, based on…