Lead Product Designer

Come join our Product 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 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 Our AI-powered platform brings efficiency and insight to workforce development, replacing outdated systems and unlocking human potential at scale.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. Your Role We're seeking a Lead Product Designer to own the look, feel, and interaction coherence of the entire FutureFit AI platform across job seeker, staff, employer, and agency-admin surfaces — and to lead the design of our largest, most complex feature initiatives end to end. FutureFit AI is the connective tissue between workers, training, and employers. That thesis only holds if the product feels like one coherent, trustworthy system to four very different audiences using it for very different reasons: a job seeker navigating a career change, a career counsellor managing a caseload, an employer posting roles and searching for candidates, and a state agency or intermediary administrator overseeing the whole program. Today the platform spans many surfaces, personas, and tenants, and it's growing fast — our flagship Massachusetts deployment is replacing the state's primary workforce platform. Without a single owner of craft and coherence, complexity compounds into accidental inconsistency and rework. You are the person who holds the experience standard for the whole product and personally designs the hardest, highest-stakes features. In your first six months, success looks like a documented, adopted design foundation in use across surfaces; a significant visual facelift of the Talent Portal shipped as a visible proof point; design leadership on at least one large, complex initiative through ship; and accessibility conformance the team builds toward by default rather than something QA catches late. What You'll Own - Platform look and feel: Own the platform's visual language and design system — components, patterns, tokens, layout, typography, and motion. You define it, document it, evolve it, and hold the bar for it. - Accessibility by default: Treat accessibility as a first-class design constraint, not a remediation afterthought. Government deployments require WCAG 2.2 AA and Section 508 conformance; you design to that standard by default and raise the team's fluency in it. - Coherence with deliberate divergence: Build a shared foundation every surface can draw from, while letting surfaces diverge deliberately where their users and jobs differ — and exercise judgment about where design depth is worth spending versus deliberately leaving areas “good enough.” - Feature design for our biggest bets: Lead end-to-end design of new product areas, major launches, and complex reworks (e.g., AI Coach, talent onboarding and registration redesigns, staff-assist tooling), partnering with Product and TPMs from problem definition through ship and iteration. - Interaction models and IA for hard problems: Design AI-mediated experiences, multi-step workflows, data-dense admin surfaces, and government-process flows like RESEA — including the trust and transparency patterns AI surfaces demand. - The full fidelity arc: Framing, concept exploration, information architecture, interaction design, prototyping, high-fidelity UI, and design-spec handoff with edge, empty, loading, and error states fully specified. - Design-led discovery: Run research directly with users and customers — job seekers (including those using assistive tech), career navigators, and agency staff — and turn what you learn into design decisions. - Craft standards and mentorship: Own the design quality gate in our product development lifecycle, and mentor and raise the design fluency of PMs, engineers, and any future designers. Required Experience - Deep product design craft across complex, multi-persona B2B/B2G or enterprise SaaS — not just consumer or marketing surfaces - Demonstrated ownership of a design system at meaningful scale - Fluency in accessible design and a track record of meeting WCAG 2.2 AA / Section 508 (or equivalent) in production, including designing conversational and data-dense interfaces accessibly - Range from systems-level thinking down to pixel-level polish, with strong IA and interaction-design fundamentals - Experience designing for AI-mediated or recommendation-driven experiences — surfacing model output, handling uncertainty, building user trust - Ability to run your own user research and synthesize it into design decisions - Comfort prioritizing where design depth matters across a wide surface Bonus Points - Experience in digital government, public benefit technology, or civic tech - Familiarity with workforce development or other regulated, compliance-heavy domains - Experience designing for multi-tenant platforms where one system serves many configurable customers - Comfort operating as the senior-most design voice in the room with executives and customers Your Education 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 [CA/US Remote] 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). Travel Expectations Although this role is remote, you may be expected to travel up to once per quarter for offsites and team gatherings. Compensation The base salary band for this role is USD $125,000 to $160,000 for candidates based in the US and CAD $115,000 to $155,000 for candidates based in Canada, regardless of location. As a remote-first company, we benchmark compensation to the national market for comparable roles at institutionally-funded startups, targeting the middle of the market. Bands are designed for the lifecycle of the role — where you enter the band reflects your applied experience and other criteria established by the hiring committee, with room to grow through the band as you grow in the role. Hiring Journey 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. Portfolio Review & 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. READY TO SHAPE THE FUTURE OF WORK? 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. COMPANY SNAPSHOT: - 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 OUR CORE PRINCIPLES - Be Curious - Drive to Outcomes - Raise the Bar - Speed Matters - Own It - We Over Me USE OF AI IN HIRING 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.