Director of Product

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 Our AI-powered platform brings efficiency and insight to workforce development, replacing outdated systems and unlocking human potential at scale.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

The Director of Product is the operating backbone of FutureFit AI's product team - the person who turns company-level strategy into a shipped, sequenced, resourced roadmap, and who makes sure every stakeholder - engineering, data, GTM, and our customers - knows what's coming and why. This is not a strategy-only seat: you will manage a team of builders (three Sr. TPMs and a Design Lead) while personally owning the connective tissue across their domains: the integrated roadmap, the capacity model, the metrics that tell us whether the product is working, and the cadences that keep several functions moving in the same direction.

Ownership Areas

• Team Leadership: 4 direct reports - 3 Senior TPMs and 1 Design Lead
• Integrated Roadmap & Capacity Plan: a single source-of-truth roadmap across all product domains, reconciled against actual engineering and data capacity.
• Cross-Company Product Cadences: the bridge meetings, monthly gates, and quarterly planning sessions that keep Build, GTM, and leadership in sync.
• Product Metrics, Tracking & Ops: the north-star and domain-level metrics stack, instrumentation standards, and the operating rhythm that makes metrics actionable.
• Product Strategy Contribution & Documentation: the living strategy docs, OKRs, and narrative artifacts that keep the roadmap grounded in "why."
• Competitive Landscape & Analysis: ongoing competitive intelligence, with particular attention to AI-native and agentic entrants in workforce tech.
• Stakeholder Management: executive, board, customer, and cross-functional relationships that sit above any single domain and need great artifacts about what's happening now, next, and later with the solution, and why.

What You'll Do
Lead & Develop the Product Team

• Manage 4 direct reports (3 Sr. TPMs, 1 Design Lead) - set goals, run 1:1s, give craft feedback on PRDs, discovery, and design work, and grow each of them toward their next level.
• Build the operating norms - rituals, discovery rhythms, documentation standards, craft bar - that let a small, high-context team punch above its weight.
• Be the escalation point when a Sr. TPM or the Design Lead needs help unblocking a stakeholder, resolving a scope fight, or navigating a resourcing conflict.

Own the Integrated Roadmap & Capacity Plan

• Maintain a single, coherent roadmap across every product domain - reconciling individual Sr. TPM roadmaps into one view that leadership and GTM can trust.
• Own the capacity plan: translate roadmap commitments into engineering, data, and design capacity, flag conflicts early, and make the sequencing trade-offs when demand outstrips supply.
• Partner with the VP of Engineering and VP of ML & AI to keep the roadmap grounded in what's actually buildable each sprint and quarter.
• Re-forecast and re-sequence in response to new state contracts, compliance deadlines, or shifting priorities - while maintaining trust in the overall accuracy and predictability of the roadmap.

Drive Cross-Company Product Cadences

• Run the recurring mechanisms that keep the company aligned: monthly stage gates, bridge-building syncs with GTM and CS, and quarterly planning sessions.
• Own the meeting architecture for product so time in the room is spent deciding, not reporting status.
• Represent product in company-wide and board-level updates, translating roadmap progress into language executives and customers care about.

Own Product Metrics, Tracking & Ops

• Own the product metrics stack end-to-end: definitions, instrumentation, dashboards, and the review cadence that makes metrics part of how decisions get made.
• Roll up domain-level metrics owned by each Sr. TPM into a company-level view tied to FutureFit's north star - lifetime wages over cost to serve.
• Build and maintain the product ops backbone - the tooling, templates, and processes that keep the org's PDLC running without heroics.

Contribute to and Maintain Product Strategy Documentation

• Own the living strategy documents - product strategy deck, OKRs, EOS-style artifacts - keeping them current as market, customer, and company context shifts.
• Translate executive-level objectives into key results that describe the work to be done in the next 2-3 quarters in a format that the broader team, board, and customers can use as a reference of record.
• Facilitate quarterly OKR refinement and ensure domain-level objectives ladder up to company strategy.

Own Competitive Landscape & Analysis

• Maintain an ongoing view of the competitive landscape in workforce tech and adjacent AI-native entrants, refreshed on a regular cadence rather than produced ad hoc for a single deal.
• Translate competitive intelligence into roadmap and positioning implications that Build leadership and GTM team can act on.
• Brief Sales, CS, and leadership ahead of competitive deals or RFPs.

Manage Stakeholders

• Be the day-to-day product point of contact for engineering, data, GTM, and CS leadership - the person those teams call when they need a product answer.
• Manage relationships with state agency and workforce intermediary stakeholders on cross-cutting product questions that sit outside any single Sr. TPM's domain.
• Keep the CPO and executive team informed with the right signal, at the right altitude, at the right time - no surprises.

What We're Looking For
Required

• Experience managing a team of PMs, TPMs, or designers directly - you know how to grow people, not just manage a roadmap.
• Track record owning a company-level (not just single-domain) product roadmap and reconciling it against real engineering and data capacity.
• Comfort running recurring cross-functional cadences - planning, gates, exec and board updates - as the person who owns the mechanism, not just a participant.
• Strong metrics fluency - you can define a metrics stack from scratch and run a review cadence that drives decisions, not just report numbers.
• Experience translating strategy into durable documentation (OKRs, strategy decks, roadmaps) that a broader org and external stakeholders rely on.
• Demonstrated stakeholder management across engineering, GTM/CS, and, ideally, enterprise or government customers.
• B2B SaaS, govtech, or workforce technology experience preferred; multi-stakeholder platforms - where the end user, the buyer, and the operator are different people - are a strong plus.

How We Evaluate Directors of Product at FutureFit AI

Drawn from the FutureFit AI Build Team Career Rubrics, Directors of Product are expected to demonstrate:

• Strategy: Owns a company-level point of view connecting the integrated roadmap to FutureFit's revenue and mission goals, with clear articulation of sequencing trade-offs across domains.
• Team Leadership: Grows direct reports' craft and scope over time; is the person the team credits for their next promotion.
• Execution & Ops: Runs a metrics and cadence operation - gates, reviews, planning - that the company relies on without reminders.
• Cross-Functional Trust: Is the default escalation point for engineering, GTM, and CS when a product question needs an answer above the domain level.
• Communication: Translates roadmap and metrics into board- and exec-ready narrative without losing technical accuracy.
• Competitive & Market Judgment: Keeps the org's view of the market current and turns it into roadmap or positioning action, not just a slide.

FutureFit AI is an equal opportunity employer. We believe workforce technology should reflect the diversity of the workforce it serves.

Compensation

The base salary range for this role is USD $150,000 to $185,000 for candidates based in the United States, and CAD $135,000 - $165,000 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.

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.