FutureFit AI

• Own the Customer Workflows domain and lead initiatives • Manage fleets of agents and ship working prototypes with AI tooling • Conduct research and product-centered discovery sessions • Author and maintain quarterly roadmaps for the Customer Workflows domain • Own trade-offs across performance, scalability, cost, and speed • Be the go-to product partner across cross-functional teams

• Own the platform's visual language and design system — components, patterns, tokens, layout, typography, and motion • Treat accessibility as a first-class design constraint • Build a shared foundation every surface can draw from • Lead end-to-end design of new product areas and complex reworks • Design AI-mediated experiences, multi-step workflows, data-dense admin surfaces • Run research directly with users and customers

• Identify, qualify, and pursue opportunities with state workforce agencies, state labor departments, and state economic development bodies. • Run discovery, manage multi-stakeholder relationships, develop proposals, navigate procurement, and close deals. • Build trusted relationships across the buyer org — from program directors and workforce commissioners to procurement leads and deputy secretaries. • Work closely with teammates who own RFP strategy and policy to ensure our responses are sharp, differentiated, and accurate. • Stay close to state budget cycles, policy priorities, federal funding flows (WIOA, TAA, and others), and competitive activity.

• The TPM — Talent Journey owns the experience of every person who walks through a FutureFit AI-powered portal looking for work, training, or a better career path. • You will own the product strategy, roadmap, and delivery quality for: - **Talent Portal:** End-to-end portal experience across onboarding, profile-building, training discovery, job matching, and progress tracking — for job seekers served by state workforce agencies, American Job Centers, and employer-sponsored programs. - **AI Coach:** Product direction for FutureFit's conversational AI coach — defining what it knows about a user, when it surfaces the right nudge, and how it improves over time through richer user profiling and feedback loops. - **Career Passport:** The longitudinal profile layer that captures skills, credentials, experiences, and outcomes across a job seeker's journey. - **Training & Job Matching Surfaces**: The search, recommendation, and eligibility-aware features that connect job seekers to training programs, apprenticeships, and open roles based on their actual profile and goals. - **Talent-Side Data & AI Use Cases:** Identify and define the LLM, recommender, and signal-capture opportunities within the job seeker journey that feed the platform's outcomes intelligence layer. • Conduct continuous, lightweight customer research (direct interviews, session reviews, portal data analysis) and synthesize findings into crisp problem statements and design hypotheses.

• Learn the product end to end and stay current as it evolves, becoming the internal expert on how it actually behaves in customers' hands. • Bring customer context into internal conversations so decisions are grounded in real usage, real workflows, and real constraints, not assumptions. • Test new and existing functionality through the lens of the people who use it, surfacing issues, friction, and edge cases before they reach customers. • Own clear, reproducible bug reports and route them with the right priority and context, so Build can act quickly and Customer Success is no longer carrying this load. • Support customer-facing delivery through implementation tasks, workflow guidance, training preparation, documentation, and lightweight troubleshooting. • Help create guides, FAQs, templates, internal notes, and other resources that make support more scalable and reduce repeated one-off questions. • Work across customers, regions, and use cases to notice patterns in where customers are getting stuck, what workflows need more support, and where the product experience can be clearer. • Work closely with Customer Success, Product, and Build to make sure customer feedback, product issues, and implementation learnings are shared clearly and followed through.

• Build, evaluate, and ship models for matching, recommendation, and ranking that directly shape the job seeker experience. • Work with skills, occupation, and career taxonomies and labor market data, improving how we represent and reason about the world of work. • Collaborate with Engineering to move models into production reliably, and monitor and improve them once they are live. • Translate messy, real-world data into clear findings and recommendations that the team and our customers can act on.

• You'll build the product that helps people get to better jobs faster and cheaper, with a focus on those facing the biggest barriers to opportunity. • As a full-stack engineer here, you'll own features end to end, from design through to production, and you'll have real influence over how we build, not just what. • Write clean, maintainable, well-tested code, and help hold the team to a high bar through reviews and shared standards. • Develop real judgment about our patterns and tradeoffs, and bring that into planning and technical discussions.

• Evaluate current pipelines, data architecture, and ML workflows, producing a prioritized, opinionated plan for what needs to change and why • Design data and ML systems anchored in customer needs and built to last • Rebuild and harden pipelines, upgrade data architecture, and ship fixes directly • Raise the bar on observability, reliability, and data quality, establishing patterns and practices for the team.

Chief of Staff Location New York Employment Type Full time Department People & Culture Overview Come join our Executive 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? 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 Opportunity Your Role 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. What You’ll Own - 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. What You Bring - Experiences, Skills, Education Required Experience - 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. Bonus Points - 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 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. The Logistics - Location, Compensation Location 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. Travel Expectations Although this role is remote, you may be expected to travel up to once per month. Compensation The base salary range for this role is 130,000USD-145,000USD or the equivalent in CAD. 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. The Hiring Journey 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: - Online Application - Initial Screen with Director of People & Culture - Interview with Hiring Manager - Performance Challenge - Final 1:1 Interviews - 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.

• Operational ownership of our video series on the future of work. Production cadence, guest pipeline, publishing rhythm. • A consistent FutureFit AI voice across the website, social, decks, episode collateral, and founder communications. • The primary distribution surface for the brand. Steady cadence of clips, posts, and supercuts. The bar is considered work that lands in a serious industry, not engagement bait. • Show notes, episode pages, guest bios, newsletter copy, founder communications. Writing is roughly half of this role. • Close work with Marketing and Growth on distribution, and with external production partners on the show.