Director, Finance and Operations

CA$120,000 – CA$150,000 | Toronto, CA

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 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 Our AI-powered platform brings efficiency and insight to workforce development, replacing outdated systems and unlocking human potential at scale.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 Director of Finance & Operations to join our team. You will serve as the internal owner of finance and operations — driving rigorous reporting, owning compliance, and partnering with senior leadership on the strategic finance work that shapes how we grow.

• Financial Reporting: Own the full monthly, quarterly, and annual close cycle — including P&L, balance sheet, and cash flow — producing accurate, timely reporting packages that meet the standards of institutional investors and board stakeholders. Serve as the primary day-to-day relationship owner with our external accounting firm.

• AR/AP & Financial Operations: Oversee accounts receivable and accounts payable processes end-to-end with our vendors, ensuring clean execution, timely collections, and accurate records. Identify and implement process improvements to billing, collections, and payment workflows.

• Strategic Finance: Partner with the VP of Strategy & Operations on budgeting, forecasting, long-range financial planning, and cash flow management. Build and maintain financial models that translate operational activity into actionable insights, and prepare investor- and board-ready materials as needed.

• Compliance & Controls: Manage North American compliance requirements — including federal and state/provincial tax filings, regulatory reporting, and audit readiness. Design and maintain internal controls and finance systems that are accurate, organized, and audit-ready at all times.

• 6–10 years of progressive finance experience, ideally within SaaS or technology companies, including ownership of strategic finance

• Deep familiarity with GAAP financial reporting and the monthly/quarterly close process

• Prior experience working within or reporting to institutional investors, or similarly rigorous reporting structures

• Demonstrated experience managing external accounting or advisory firm relationships

• Exposure to strategic finance functions: budgeting, forecasting, board reporting, and cash flow management

• Strong command of North American (Canadian and US, cross-border ideal) compliance and tax requirements

• Advanced Excel or Google Sheets skills; proficiency with accounting platforms such as QuickBooks

• Exceptional attention to detail — you catch errors others miss and hold yourself to an uncompromising standard of accuracy

• Comfortable operating independently, managing competing deadlines, and knowing when to escalate

Bonus Points

• CPA designation

• Experience in a lean, high-growth startup where you've had to build processes from scratch

• Familiarity with equity reporting or cap table management in a funded company context

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.

Location: This role is based in Toronto. Our office is conveniently located at 325 Front St West (a short walk from Union Station). The team comes in 1–2x a week, usually on Wednesdays. We'd love to see you too!

Travel Expectations: You may be expected to travel up to once per quarter.

Compensation: The base salary range for this role is CA$120,000 – CA$150,000. This range reflects the varying levels of expertise and responsibilities that will be determined through the interview process, based on applied experience and other criteria established by the hiring committee.

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.