Staff Product Designer — AI Playbook Automations

Clio; Toronto; Hybrid; CAD 150,000 - 226,000; Full time

Benefits offered by this job

Competitive salary and benefits

Hybrid in-office schedule (Anchor Days

20 days paid time off

$2000 annual counseling benefit

RRSP matching and RESP contribution

Clioversary recognition program

Job summary

Clio is seeking a Staff Product Designer to lead the design of playbook automations within Clio Work, partnering with the drafting team to craft AI-powered experiences that run end-to-end for legal matters. This hands-on role focuses on owning outcomes, prototyping with engineering, and shaping direction across multiple products and teams.

You will contribute to a high-performing, user-centered design organization, evolve Clio’s design system, and collaborate closely with product, engineering,

Qualifications

• 12+ years of Product Design experience. B2B SaaS experience is preferred, but not required.
• Direct experience shipping AI-powered features or workflows, with a strong understanding of user-centered applications of machine learning and generative AI.
• Experience designing complex workflows or features forenterprise-type applications, on desktop and web rather than consumer or mobile.
• Demonstrated ownership of an entire product, not only features within one, including the ambiguity and strategic framing that comes with it.
• Experience with work that crosses product boundaries and spans multiple products or customer segments.
• Strong product thinking, with the ability to set direction where product direction is still forming.
• Extensive partnership with Engineering, including the ability to prototype quickly and iterate alongside them.
• Experience working in-house at a product company rather than in a consultancy or agency model, with deep understanding of a specific user group.
• Strong narrative and presentation skills, with a track record of pitching ideas and visions upward and winning buy-in.
• The ability to navigate ambiguity and hold a position amid divergent or incomplete direction.
• Strong craft across interaction design, information architecture, usability, and visual design, with consistently high-quality execution.
• Experience with accessibility standards (WCAG).

Responsibilities

• Own a product area: Lead design for playbook automations end-to-end, from vision and ideation through prototyping, testing, and polished production work.
• Design for AI: Ship AI-powered workflows where the right experience depends on how the model behaves, exercising judgment about trust, explainability, and the appropriate level of automation and control.
• Prototype with engineering: Partner closely and continuously with Engineering, prototyping quickly to learn what is possible rather than specifying ahead of the technology.
• Set direction: Bring strong product thinking to an area that needs clearer direction, framing opportunities and shaping strategy alongside Product and Engineering.
• Work across boundaries: Design experiences that span product boundaries, connecting drafting coherently to the rest of Clio Work and the wider Clio platform.
• Raise the quality bar: Deliver polished, accessible, cohesive experiences across a high-complexity surface area.
• Build the narrative: Pitch ideas and visions upward, build buy-in through clear storytelling and decision framing, and hold a well-reasoned position amid ambiguity.
• Contribute to the design system: Evolve Clio’s design system, identifying gaps and improving consistency beyond your immediate scope.
• Create leverage for the team: Raise the bar through constructive critique and by partnering with more junior designers to execute.

Skills

Product design leadership

AI-powered features

Enterprise workflow design

Ownership of product

Cross-product collaboration

Product strategy

Engineering collaboration

In-house product company experience

Storytelling & presentations

Ambiguity navigation

UX/UI craft

WCAG accessibility

Job description

Clio is seeking a Staff Product Designer to lead the design of playbook automations within Clio Work, partnering with the drafting team to craft AI-powered experiences that run end-to-end for legal matters. This hands-on role focuses on owning outcomes, prototyping with engineering, and shaping direction across multiple products and teams.

You will contribute to a high-performing, user-centered design organization, evolve Clio’s design system, and collaborate closely with product, engineering,