Product Design Lead (Canada)

Proof Technology; Canada; Remote; CAD 55,000 - 96,000; Full time

Benefits offered by this job

Fully Remote

Equipment provided

Flexible Time Off

Job summary

Proof Technology is seeking a Senior Product Designer to take on challenging product and service workflows, with a primary focus on onboarding workflows powering legal document delivery. You will partner with Product, Engineering, and Operations leadership to frame ambiguous problems and shape direction before solutions are locked in.

You’ll own complex workflows end-to-end, prototype to learn, and design whole systems across digital tools and operational processes.

Qualifications

• Service & operational craft: Experience designing for internal operations, complex systems, or expert users where workflow efficiency and trust are paramount.
• Rapid context-building: Ramp up quickly on complex systems through shadowing and real workflows.
• Change in established environments: Experience introducing thoughtful change inside organizations with deep tribal knowledge.
• Influence & partnership: Shaping product and technical direction across disciplines without formal authority.
• Craft & collaboration: Create reusable design patterns and critique to improve team work.
• End-to-end ownership: Lead ambiguous product work through shipped delivery with clear tradeoffs.
• Prototyping: Build prototypes at varying fidelities to explore ideas and get early feedback.
• Workflow domain: Experience in legal tech, logistics, marketplaces, or field-service products, with automation savvy.

Responsibilities

• Own complex workflows end-to-end from framing problems to delivery.
• Prototype to learn and test assumptions to inform decisions.
• Design whole systems—interfaces, information architecture, and state across tools and processes.
• Collaborate with Product, Engineering, and Operations to shape direction before solutions are locked in.
• Share unfinished work early and invite critique to strengthen craft and service thinking.

Skills

End-to-end ownership

Prototyping

Cross-functional collaboration

Systems design

Workflow design

Job description

• We’re looking for a Senior Product Designer to take on challenging product and service workflows, with a primary focus on the onboarding workflows that power legal document delivery
• Delivering documents in the real world comes with inevitable edge cases and complications. An action in the field ripples through our internal systems and what a law firm sees. For example, if a process server finds a recipient has moved, the law firm needs clarity, internal teams need to resolve the exception, and the delivery workflow changes
• Designing here means understanding those connections and deciding whether the right intervention is software, a process shift, automation, or all three
• You’ll report directly to the Director of Design on a small, high-leverage team, partnering with Product, Engineering, and Operations leadership to frame ambiguous problems, explore tradeoffs, and shape direction before solutions are locked in
• You’ll have meaningful autonomy to frame problems, choose the right approach, and drive work forward, with close cross-functional partnership, not a prescribed playbook
• Own complex workflows end-to-end: Aid in framing problems, navigate ripple effects across operations, servers, and customers, and drive through to delivery
• Prototype to learn: Build prototypes at the right fidelity to test assumptions, make ideas tangible, and help teams make clear decisions early
• Work with the hood open: Share unfinished work early, invite critique, and partner with Product, Engineering, and operations while problems are still malleable
• Design whole systems, not just screens: Create coherent workflows, interfaces, information architecture, and states across digital tools and operational processes
• Contribute to the practice: Create and improve interaction patterns and language within your work that help Operations specialists, process servers, and law firms move through the product without having to re-learn it. Share what you learn and work alongside other designers to strengthen craft and service thinking
• Part of the work here is strengthening how we build context, shifting toward an everyday habit, not a scheduled research phase. Rather than wait for complete briefs, we dig into the mechanics of the service by shadowing Operations specialists, listening to law-firm calls, talking with process servers, and asking questions until we have a solid understanding. From there, we move fluidly between sketching, prototyping, and writing clear recommendations to help teams make confident decisions while the problem is still open

Benefits

• Full time, hourly position
• Medical, dental, vision, and disability insurance and 401K available
• Phone and Internet monthly stipend
• Flexible Time Off and Holidays
• Fully Remote - ideally within the location of market you manage
• Equipment provided

Service & operational craft: Experience designing for internal operations, complex systems, or expert users where workflow efficiency and trust are paramount. You balance speed with clarity and accuracy, especially when mistakes have consequences beyond the interfaceExperience: Product design experience, or equivalent demonstrated expertise, including independently owning end-to-end design for complex product or service workflowsRapid context-building: High domain curiosity and the ability to ramp up quickly on complex systems. You treat learning as a continuous habit, shadowing, listening to users, and digging into real workflows to develop a grounded point of view while the problem is still openChange in established environments: Experience introducing thoughtful change inside organizations with established workflows and deep tribal knowledgeInfluence & partnership: A history of shaping product and technical direction across disciplines without relying on formal authorityCraft & collaboration: Experience creating reusable design patterns, contributing thoughtful critique, and helping other designers improve their workEnd-to-end ownership: Proven track record leading ambiguous product or service work through shipped delivery, with clear reasoning and tradeoffsPrototyping: Comfort building prototypes at varying fidelities to explore ideas, communicate intent, and get early feedback from users and teammatesLegal technology, logistics, marketplaces, or field-service productsWorkflow automation or AI-assisted products, with sound judgment about where automation creates leverage and where human judgment, transparency, and restraint matter more