Director / Head of Data & AI

FutureFit AI is looking for a Director / Head of Data & AI. to lead our growing team The exact title (Director or Head of Data) will be determined based on the candidate's qualifications, experience, and the needs of our team as we scale. We have a culture of high trust, high impact, high velocity, and a gritty determination to win. If you are passionate about data leadership, enjoy building and scaling products, and driven to make a positive social impact, we would love to hear from you

First, an important note: Data shows that men on average apply for a role if they meet 3/10 requirements while women often only do so if it’s 10/10. We work hard to be clear and specific about what our roles include and demand and encourage you to apply if you see a strong (but not necessarily perfect) fit between you and the opportunity.

About You

• B2B Startup Experience - You have a proven track record of leading data and AI strategy, development, and evaluation processes in a B2B / B2B2C startup environment, working closely with founders to drive strong execution and expansion through data. You are excited by solving complex multi-dimensional business problems across a multi-portal product for multiple customer and user personas.

• Team Leadership - You have 3+ years of experience leading and building high-performing teams designed to work quickly and cross-functionally with technical and business stakeholders. You have experience coaching teams on all stages of model development from discovery and design to evaluation.

• Data Strategy - You are adept at collaborating and driving data / AI strategy, with accountability for data sources, model, algorithm, and recommender systems execution across the organization. You have a strong background in working alongside product and engineering teams to contextualize data features in the product experience.

• AI Product Expertise - You bring proven data and AI expertise to the table, with past exposure and experience in building AI-driven products and deploying models / algorithms in a production environment. You have deep exposure to NLP models, LLMs, and recommender systems, as well as implementation of ontology frameworks to standardize data structures. (Past experience with labor market data is a plus.)

• Full-stack Data Portfolio: You have the necessary breadth of knowledge, skills, and experiences to manage a full-stack data portfolio covering data analysis, data science, data engineering, MLOps, and GenAI.

• Grit - You like to solve challenging problems, are not afraid of the unknown, and are eager to learn and adapt in a fast-paced environment. You still like to get into the weeds You’re not shy about jumping into technical discovery, iterating on architecture and design, writing code, and solutioning alongside your team.

• Deeply Curious - You lead with curiosity in everything you do. You constantly seek to understand the 'why' behind user behaviors, customer pain points, and product feedback. This curiosity drives you to ask the right questions, explore new ideas, and push the boundaries of what's possible. You aren't afraid to challenge conventional thinking or blur boundaries in your pursuit of driving success forward.

• Extreme Ownership - You take radical responsibility for outcomes of the business. You’re not just delivering on product requests and requirements--you seek to understand the problem, find solutions, and direct each step towards success. You lead by example, holding yourself and your team accountable for delivering high-quality results, and have the resilience and determination to push through obstacles and drive projects to successful completion.

• Lead all aspects of data strategy and execution, collaborating closely with senior leaders to drive the data vision, define strategic objectives, and develop the data roadmap.

• Continue to build and mentor a high-performing data team, hiring and guiding data scientists, data engineers, and analysts who can excel and grow with the company.

• Develop and refine internal data processes to improve accuracy, velocity, and quality in partnership with engineering and product leadership.

• Work closely with business, product, and engineering teams to define data requirements for key initiatives and platform features.

• Engage with and drive design approaches for technical data stacks, including pipelines, databases, and analytics tools for scalable data solutions.

• Lead the development and optimization of NLP models, LLMs, and scalable recommender systems, in support of product objectives for multiple user personas.

• Design and implement ontology frameworks to standardize data structures, with a focus on leveraging labor market data to drive accurate and consistent model outcomes.

• Enable data-driven decision-making by executing data initiatives that build infrastructure and analytics capabilities aligned with business objectives.

• Create and manage data communication processes, including dashboards, reports, documentation, and insights to support stakeholders.

• Integrate multiple factors into data requirements, such as internationalization (ex. multilingual models), scalability, performance, and product experience.

• Establish and manage cross-company data governance practices, including data quality standards, responsible AI practices, data privacy protocols, and data lifecycle management, while considering regulatory requirements, including SOC2, GDPR, and IT security / privacy standards.

This role will be based in either our Toronto or NYC offices. While we are remote-friendly and don’t expect you to be in the office every day, we place a high value on weekly face-to-face collaboration and team building. We will only consider candidates who live in or are willing to relocate to the Toronto or NYC area.

The base salary range for this role is $180,000 to $220,000, plus equity. 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, we believe in designing intentional and rigorous hiring journeys to help you determine if this is the best role and organization for you, based on your unique skills, mindset, and experiences. We operate at high velocity with high intensity and want an accurate taste of what that feels like before you get through the door.

Every hiring journey at FutureFit AI consists of thoughtfully crafted steps including a performance challenge and rounds of interviews with team members. For this role, that might look like:

1. Online Application

2. Initial Screen/Checkpoint

3. Performance Challenge and Debrief

4. Final 1:1 Interviews

5. Final Decision

Generally, this entire process takes around 4 weeks, although the timing can vary due to specific candidate circumstances.

In looking at a job posting, it’s often hard to get a basic picture of the company profile (size, stage, structure, etc.) which is why we are sharing it with you upfront. This helps you quickly decide and helps us focus any time we spend together on going beyond the basics:

1. Problem Domain: Future of Work / Workforce Development - important that the problem domain interests you even if you haven’t worked in the space before.

2. Industry: SaaS / AI - technology and data are at the core of what we build.

3. Customers: We partner with workforce development agencies, government agencies, and employers/enterprises.

4. Structure: We are organized around the following key departments: Growth, Customer Success, Product, Engineering, Data, People & Culture, Finance & Operations.

5. Team: We are a team of 30-50 across US and Canada with main hubs in New York and Toronto.

6. Funding: We built the company from 0 to 1 with no external capital (a rare feat for tech startups) and have subsequently raised one round of funding led by JP Morgan which fueled a significant growth trajectory for us.

• Be Curious

• Drive to Outcomes

• Raise the Bar

• Speed Matters

• Own It

• We Over Me

At FutureFit AI, we’re on a mission to unlock pathways between talent and opportunity using the power of AI. We focus on personalized, AI-powered career guidance for job seekers, emphasizing skills over extensive resumes, and partner with workforce development partners, governments, and employers to level access to opportunity.

FutureFit AI is a growing, venture-backed company focused on using technology to improve the lives and outcomes for people going through career transitions. We’re a small, driven team, united by our commitment to the job seekers and workforce ecosystems we serve. We're not just building a company; we're shaping the future of work.

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.