CPTO

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 Our AI-powered platform brings efficiency and insight to workforce development, replacing outdated systems and unlocking human potential at scale.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.

The Chief Product & Technology Officer will be a key executive leader who defines and shapes the future of technology for workforce development. Reporting to the CEO, this leader will be responsible for overseeing the entire build organization, including product, engineering, and data.

This is a rare opportunity to serve as a trusted partner for go-to-market efforts and senior leadership, while leading a lean, high-velocity team. The CPTO will be instrumental in scaling our technical and talent pipelines to support our rapid growth in government and complex enterprise environments.

This role is not simply about managing technology, but about leveraging AI-first approaches and a deep domain literacy to deliver scalable, mission-critical solutions. You will be at the nexus of technology and our core business goals, ensuring every technical decision drives meaningful social impact and prepares FutureFit AI for its next chapter of market leadership.

• Product & Technology Strategy & Vision

  • Define and evolve the company's product vision, integrated development roadmap, and overall build strategy to align with business goals and market opportunities.

  • Champion a data-driven approach, leveraging metrics and customer insights to inform decision-making across the build organization.

  • Lead the discovery and development of new technologies, especially in the application of LLMs and other AI/ML approaches to workforce development challenges.

• Execution & Delivery

  • Oversee the end-to-end product development lifecycle, ensuring cost-effective and rapid delivery of consumer-grade digital solutions that meet enterprise-grade deployment requirements

  • Ensure the company's technical infrastructure is robust, secure, and scalable to support current and future growth.

  • Balance the delivery of short-term features with long-term platform innovation and architectural scalability.

  • Establish and track key performance indicators (KPIs) and objectives and key results (OKRs) for the build organization, ensuring measurable results.

• Team Leadership & Scaling

  • Build, lead, and mentor a high-performing and integrated product, engineering, and data team.

  • Establish and grow technical and talent pipelines, fostering scalable skills and capabilities within the organization.

  • Foster a culture of excellence, innovation, and accountability that is aligned with the company's public benefit mission.

  • Work cross-functionally to ensure strong collaboration with go-to-market, operations, and other senior leadership teams.

• 5+ years of build experience, including 3+ years in a senior leadership role (CPO, CTO, VP of Product / Engineering / Data, or equivalent).

• Proven track record of building and scaling enterprise-grade tech solutions in high-stakes environments.

• Demonstrated experience in a leadership role within a lean team (30-50 people), delivering features rapidly using AI-first approaches, especially with LLMs.

• Deep expertise in systems architecture, cloud computing, and cybersecurity.

• Strong commercial mindset with a history of driving business growth through product / technology strategy.

• Experience leading cross-functional teams and fostering alignment across product, engineering, and data functions.

• Ability to balance high-level vision with tactical execution, ensuring both immediate delivery and long-term innovation.

• Experience building solutions for human services, workforce development, or public sector domains (GovTech) is a strong plus.

• A background or deep literacy in the public benefit and mission-driven space.

• Experience with government procurement and complex customer environments.

• A proven track record of mentorship and team development in a fast-growing startup.

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 the US or Canada. For candidates living in New York City, our office is at 18 W 18th Street. 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 1-2x per quarter for team offsites or key industry events.

This role offers a competitive compensation package, including bonus and equity. The package will reflect 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 Executive Recruiting Partner

   • Optional: Submit a 2-minute video along with your application for a chance to accelerate straight to a call with our team.

3. 1st interview with CEO

4. Performance Challenge

5. Presentation to Team Panel

6. 1:1 Interviews with Executive Team Members

7. Final Decision

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.