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 React/Next.js 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.