Senior Product Designer - Toronto - Proof

Description

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About Proof

We're Proof, a high-growth company in the legal tech industry founded in 2017. We've built a best-in-class legal services platform used by thousands of law firms with a sustained average growth rate of over 10%. Our marketplace platform helps law firms and pro se parties access more efficient, transparent, and accessible legal services that are not traditionally available to everyone. Our primary services are Service of Process and E‑Filing. We currently support over 3,000 law firms throughout the US and countless pro se parties.

About the Role

We're seeking a Senior Product Designer to join our design team. You'll own design work across multiple product areas and help us think strategically about where we're headed. We're scaling fast across all 50 states, each with its own legal requirements, court systems, and client specs. Your job is to take these complex and nuanced operational challenges and turn them into workflows that actually make sense so our ops team can do their jobs with confidence. You'll work with engineering squads, PMs, and ops folks to figure out what's actually broken, advocate for the people using our tools, and ship things that make their work faster and more accurate.

What You'll Do

• Own design work across multiple squads – balance hands‑on work with thinking about how everything fits together
• Talk to the people using our tools – figure out what's frustrating them, where we could automate, and validate ideas before we build them
• Design interfaces that reduce cognitive load – our ops team deals with complicated workflows; make them feel simple
• Spot opportunities for AI and automation – find places where we can save people from repetitive work and reduce errors
• Turn legal/technical requirements into tools people can actually use – translate the complex stuff into something organized and intuitive
• Work with our design system (Atlas for web, Compass for mobile) – use what we have, extend it when needed, keep things consistent
• Coach and grow the team – mentor other designers by sharing feedback, frameworks, and perspective to help them grow
• Partner with engineers – push for good UX while being realistic about what we can ship quickly
• Make prototypes that show how things work – especially for complex interactions and different states
• Actually measure if your designs work – look at things like task completion time, error rates, and whether people are happier

What You'll Design

• Document management systems with smart templates and quality controls
• Workflow tools that guide people through complex multi‑step processes
• Interfaces that surface the right information at the right time based on context
• AI‑enhanced tools that reduce manual work and improve accuracy
• Issue tracking and quality control systems
• Checklists and decision‑support tools for compliance‑heavy workflows

What We're Looking For

Must‑haves

• 5‑7 years designing tools or enterprise software – the kind with real complexity, not just marketing sites
• You're good at organizing chaos – look at a mess of requirements and figure out a system that makes sense
• You've shipped things that made work easier – and you can show how you know it worked (faster tasks, fewer errors, happier users)
• You know how to learn from users – talk to people, validate assumptions, don't just guess what they need
• You can break complex stuff into simple steps – core skill for this role
• You're pragmatic – ship something good rather than wait for perfection
• You've worked with design systems – use components and know when to extend them
• You work well with engineers and PMs – productive conversations about trade‑offs
• You can explain your thinking – both the "what" and the "why" behind your decisions
• You're solid with Figma and FigJam – main tools

Nice‑to‑haves

• Interest in AI/automation (exploring a lot)
• Experience with legal, compliance, or regulated industries
• Background in operational tools or back‑office software
• Information architecture or service design experience

You'll Thrive Here If

• You're passionate about creating order from ambiguity
• You believe function drives form, not the other way around
• You believe in understanding user workflows deeply before proposing solutions
• You think systematically about how all pieces fit together
• You're comfortable with iteration and measuring impact through metrics
• You're interested in the potential of AI to transform operations
• You're motivated by creating tools that make people's work lives easier and more efficient
• You can balance strategic thinking with hands‑on execution
• You bring a sense of humor to work – serious problems, but we don't take ourselves too seriously

Portfolio Requirement

We need to see your portfolio with case studies that show your process – not just the final pretty screens. We want to understand how you think through problems, do research, work with constraints, and make decisions. No portfolio = we can't move forward with your application.

During interviews, you'll walk through 2‑3 projects that demonstrate:

• Systems thinking and organizing complex requirements
• Working with engineering and product constraints
• User research and validation process

Compensation & Benefits

• Salary range: $130,000 - $160,000 CAD based on experience and location
• Full‑time, salary, remote position
• Flexible Time off and paid holidays
• Healthcare, Dental, Vision, and Disability insurance available
• Necessary equipment provided

This company participates in E‑Verify, for more information view the Participation and Right to Work Posters.

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