Who you are

- 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

What the job involves

- 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

- 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 excellent artifacts about what’s happening now, next, and later with the solution, and why

- 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

- 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

- 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 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

- 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

- 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

- 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

Benefits

- Dual hubs: experience the best of both worlds with our offices in vibrant Toronto and bustling New York

- Founder access: work shoulder-to-shoulder with our visionary founding team to shape the future of AI

- Growth investment: Accelerate your career with our dedicated professional development budget

- Unlimited time off: recharge and explore with our trust-based, limited paid time off policy

- Comprehensive healthcare: rest easy with our robust health coveage, proioritizing your well-being

- Future-proof savings: Build your financial security through our 401k plan

- Tech enablement: Stay cutting-edge with our technology reimbursement program

- Flexible lifestyle: Achieve work-life harmony with our flexible, trust-based scheduling

📌 Director of Product (Canada)
🏢 FutureFit
📍 Canada