Product Designer

2 weeks ago

Montreal, Quebec, Canada Optionality Full time

About Us:

Optionality is building the operating system for business owners to help them navigate an exit. It's an owner-first platform that provides real clarity on valuation, buyer fit, benchmarking, exit readiness, and exit planning. Our product combines
quantitative data, qualitative insights, and generative AI
, and is already used by business owners, advisors, and acquirers to make better decisions, faster.

The Role:

As the Senior Product Designer, you'll design across the entire product lifecycle - from early concepts to high-fidelity UI. You'll take over existing modules that already have core UX structure, refine and elevate the UI, and within 1–2 months transition into full ownership of UX + UI for new features and product expansions.

  • Location: Hybrid / Remote Canada
  • Experience: 4–6 years
  • Type: Full-Time

What You'll Do:

Full product design ownership

  • Lead
    end-to-end design
    for new modules/features - from ideation to wireframes to high-fidelity UI
  • Lead the re-design of our entire application, simplifying core flows & functionality
  • Partner on product exploration, user flows, experiments, and iterative UX improvements
  • Translate complex workflows (multi-step onboarding, exit planning, data-driven insights) into simple, intuitive experiences
  • Build & evolve a scalable internal design system (Tailwind/tokens/Twilio Paste/etc.)
  • Contribute to product strategy, UX architecture, and shaping how business owners interact with their data
  • Champion design thinking, user empathy, and a high-quality bar across the team

What We're Looking for:

Must-Have Experience

  • 4-6 years in product design with exceptional UI craftsmanship as a core strength (while also capable across UX research, flows, and wireframes).
  • Experience in early-stage B2B SaaS or B2C tech
  • Experience shipping real product in
    environments
    , and comfortable working closely with engineers
  • Strong UI craft - elegant, polished, crisp visual designs that elevate a complex product
  • Strong UX thinking - able to break down complex workflows into simple flows and wireframes
  • Demonstrated ability to
    articulate design decisions
    , defend rationale, and communicate trade-offs clearly
  • Ownership mindset - comfortable iterating quickly, making decisions, and working in ambiguity
  • Experience designing data-heavy interfaces (dashboards, workflows, multi-step tools, card systems, etc.)

Nice-to-Have

  • Experience with
    Tailwind, Twilio Paste, Radix UI, or other component systems
  • Experience with AI tools to streamline prototyping such as Cursor, Figma Make, UX Pilot, etc
  • Familiarity with dashboards, AI-assisted UX, or workflow-heavy products
  • Experience designing for mixed user personas (B2B + B2C style users)
  • Motion/interaction design skills for polishing modals, transitions, onboarding, etc.

You'll be a great fit, if you:

  • Love bringing structure to ambiguity
  • Care deeply about typography, spacing, hierarchy, and clean execution
  • Want to have real responsibility and shape the product direction
  • Thrive in fast-moving environments where you can ship
    daily
    , not quarterly
  • Want to be the foundation of a future design team

What we offer:

  • Competitive compensation + potential equity
  • Ability to shape the design culture, standards, and future hires
  • A product team that moves insanely fast, values design deeply, and executes
  • Ownership of major product areas and greenfield design opportunities
  • Work directly with founders on product strategy, UX, and customer insights
  • Flexible working structure (hybrid) and in some cases fully remote.

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