tailkLOCATION: Remote anywhere in Canada
About Proof
Proof is the service-of-process marketplace modernizing how legal documents move through the real world. 10,000 law firms trust us with documents that have legal consequences: a serve has to reach the right person, at the right address, under the right rules, with a court-ready affidavit proving what happened.
That promise only looks simple from the outside. Underneath is a multi-sided operating system: customer intake, jurisdiction-specific logic, server dispatch, mobile field workflows, exception handling, affidavits, and ops tooling all have to work together without exposing the mess to the user.
Great design here means making the complex feel effortless — for customers under pressure, independent servers in the field, and the internal teams keeping the network moving.
The role
As Director of Design, you'll help decide what Proof builds and how it gets built. You'll report to the CPO, sit on the tech leadership team, and partner directly with Product, Engineering, and the executive team.
Design at Proof is not a downstream execution function — it is part of how we understand customers, choose problems, set strategy, and turn legal complexity into products people trust. You'll coach a team, raise the quality bar across squads, and stay close enough to the work to raise its quality.
What you'll own
- Product strategy through design. You'll be a strategic partner to the CPO and CTO, helping teams decide which problems matter, what good looks like, and how customer insight should shape the roadmap.
- The end-to-end product experience. You'll lead design across the full Proof system: customer workflows, field tools for independent servers, internal operations workflows, new product surfaces, and the connective tissue between them.
- Our design system and interaction patterns. We've built a foundation we're proud of. You'll evolve it, drive deeper adoption across squads, and make sure it keeps creating leverage as the product grows across web and mobile.
- Customer understanding as a team habit. You'll build lightweight research practices that keep designers and product teams close to real users, real workflows, and real tradeoffs.
- AI product judgment. You'll help define where AI can make Proof faster, clearer, and more reliable — and where restraint, transparency, and trust matter more than novelty. The cost of a wrong serve isn't a bad UX. It's a dismissed case. Trust is the product.
- A high-leverage design team. You'll manage two excellent designers, hire thoughtfully to grow the team, and build the operating rhythm for a team that stays close to the work and raises the bar across every squad.
- Brand as part of the product experience. You'll own the quality and consistency of how Proof shows up — not as a separate brand exercise, but as part of earning trust in a serious, high-stakes category.
How we think about design
- Simplify to amplify. The work is complicated. The product shouldn't feel that way.
- Talk to humans. Ground decisions in real research, not assumptions.
- Clarify consistently. Use patterns in language, structure, and interaction so users don't have to re-learn the product.
- Design for trust. In legal workflows, clarity, accuracy, and restraint matter as much as speed.
Who we're hiring
We're looking for a design leader who moves fluidly between product strategy, systems thinking, and hands-on craft. All three are part of the job.
You'll be a strong fit if:
- You've designed complex, multi-actor B2B workflows where the hard part was understanding the work, not decorating the screen — and you can turn that mess into a product that feels clear, trustworthy, and fast.
- You think in patterns, information architecture, and reusable systems — and you know when a design system creates leverage versus slows people down.
- You've managed designers with range: hiring, coaching, giving direct feedback, raising craft, and helping strong ICs grow into product thinkers.
- You can influence product strategy with customer evidence, not just design taste. You're comfortable pushing on the problem, the sequencing, and the tradeoffs.
- You're excited to stay close to the work. You don't need to be the primary designer on every project, but you should still be able to make the work better in Figma, in critique, and in product conversations.
- You move quickly without becoming sloppy. You know when to ship, when to sharpen, and when the team needs a stronger point of view.
Bonus points if you have:
- Experience in legal tech, logistics, marketplace operations, support tooling, or another domain where the workflow is the product.
- Strong product instincts around AI: where it creates real leverage, where it creates risk, and how to make it useful instead of gimmicky.
- Cross-platform experience across web and mobile.
- Experience building or resetting design quality in a Series B/C environment.
This probably isn't the right seat if:
- You want to manage managers more than shape the work.
- You haven't been meaningfully hands-on in the last couple of years.
- You reach for heavy process before understanding the problem.
- Your portfolio is primarily brand or visual design without deep product work.
- You want a large org, more management layers, or a title path that pulls you away from the product.
Why now
Proof is gaining market share quickly, and the platform is getting more complex as we grow. Your job is to keep the experience effortless as the surface area scales — because effortless is what compounds into leverage in a category like ours.
This role comes with autonomy, real strategic surface area, and direct exposure to leadership in a company moving fast. It's one of the last leadership seats on an experienced tech team building best-in-class software in a category most people overlooked. We'd like you to help shape what comes next.
Benefits:
- Full-time, salary position
- Fully remote role, based in Canada
- Flexible time off and holidays
- Equipment provided
- Comprehensive benefits package, including healthcare, dental, and disability insurance
Compensation:
- 220,000 - 250,000 CAD based on experience and location. Must be located in Canada
- Eligible to participate in company bonus plan