Chief of Staff

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 FutureFit 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 Our AI-powered platform brings efficiency and insight to workforce development, replacing outdated systems and unlocking human potential at scale.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 Chief of Staff 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 judgment 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 a Chief of Staff

• 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). For candidates living in New York City, our office is at 18 W 18th Street. 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.

At FutureFit AI, our hiring process is designed to help you assess whether this role and our culture are the right fit based on your unique skills, mindset, and experiences. We move fast and work with intensity, so we want you to get a real sense of that from the start.

Each journey includes a mix of interviews and a performance challenge. For this role, that might look like:

1. Online Application

2. Initial Screen with Director of People & Culture

3. Interview with Hiring Manager

4. Performance Challenge

5. Final 1:1 Interviews

6. Final Decision

Generally, this entire process takes around 6 weeks, although the timing can vary due to specific candidate circumstances.

At FutureFit AI, we're not just building a company—we're transforming how talent and opportunity connect. Join our driven team united by a commitment to job seekers and the workforce ecosystems we serve.

• Team: 30-50 across US and Canada (hubs in NYC and Toronto)

• Customers: Workforce development agencies and intermediaries, government agencies, employers

• Industry: SaaS/AI technology

• Funding: Bootstrapped 0-1, then raised funding led by JP Morgan

• Structure: Growth, Customer Success, Product, Engineering, Data, People & Culture, Finance & Operations

• Be Curious

• Drive to Outcomes

• Raise the Bar

• Speed Matters

• Own It

• We Over Me

At FutureFit, we use artificial intelligence (AI) tools to make our hiring process more efficient, consistent, and equitable—never to replace human judgment. We use AI in the following ways:

• Screening support: AI may help us compare applications against the skills and experience required for a specific role. These skills are defined by the hiring team for each position. A human reviews each application, with the AI assessment as just one input.

• Interview support: In some interviews, we may use an AI notetaker to summarize the discussion so interviewers can focus on being present in the conversation.

• Insights, not decisions: AI provides data points to support our team’s evaluation but does not make or recommend final hiring decisions. Every hiring decision is made by people.

We will ensure that individuals with disabilities are provided reasonable accommodation to participate in the job application or interview process, perform essential job functions, and receive other benefits and privileges of employment. Please contact us to request an accommodation.

© FutureFit AI All rights reserved, we are proud to be an equal opportunity workplace. We celebrate diversity and are committed to creating an inclusive environment for all employees. We do not discriminate on the basis of race, religion, color, gender identity, sexual orientation, age, disability, veteran status, or other applicable legally protected characteristics. We encourage people of different backgrounds, experiences, abilities, and perspectives to apply.