Senior UX Designer

Caseware•Toronto, ON

3d•CA$105,000 - CA$115,000•Hybrid

About The Position

Caseware is seeking a Senior UX Designer to take ownership of complex design problems at the intersection of design craft and AI-assisted making. The UX Design Team is transforming how design work is done by integrating tools like Figma Make, Claude Code, and Replit into daily practice. This role will help shape that evolution while designing user experiences for cloud-based audit, financial reporting, and data analytics solutions used by accounting professionals globally. The designer will collaborate closely with Product, Engineering, and Design Teams to create experiences that enable accounting and audit professionals to navigate complex, regulated work with confidence and clarity. This is a full-time permanent position and a new vacancy. The role is hybrid, requiring 3 days a week in the Toronto office.

Requirements

A genuine enthusiasm for working at the intersection of design craft and AI-assisted making, paired with an understanding of responsible AI principles (bias, transparency, accountability, designing for trust) and the critical thinking to keep speed and automation from compromising user-centred outcomes.
At least 3 years of professional UX experience, with a portfolio that demonstrates not just what you designed but how you led others through the problem and made design decisions under ambiguity.
Fluency with AI-assisted tools like Figma Make, Claude Code, and Replit, including prompting effectively, building custom workflows, evaluating generated output, and refining it to meet design-system and accessibility standards.
Design experience with, or a clear perspective on, human oversight moments in agentic or AI-driven features, including how to think about accountability, transparency, and user control in that context.
Experience planning and leading end-to-end user research programs, including the use of AI to synthesize findings and identify patterns across usability testing cycles.
Proficiency with Figma and related design and prototyping tools, substantial experience working within and evolving a component-based design system, and a strong working knowledge of accessibility standards, including the ability to evaluate AI-generated components for compliance and usability gaps.
Confidence representing design direction to senior stakeholders like Team Leads, product leadership, and external partners, and the ability to drive cross-team initiatives that require sustained collaboration and consensus-building without formal authority.
Experience mentoring junior or intermediate designers, giving clear and constructive feedback that helps them grow, alongside strong communication skills in both facilitating design discussions and presenting design reasoning to non-design audiences.

Nice To Haves

Knowledge of accounting, audit, or financial services industries is a bonus.
Prior experience designing for AI-powered or conversational product features.

Responsibilities

Design exceptional user experiences for Caseware’s cloud-based audit, financial reporting, and data analytics products, taking features from problem framing through to implementation with a modern toolkit that pairs Figma Make, Claude Code, and Replit with traditional UX methods.
Shape how the team brings AI into its everyday design practice, evaluating new tools, sharing what works, and moving fluidly between AI-assisted and manual modes so design judgment stays at the centre of every decision.
Design the human oversight moments inside agentic workflows, deciding what users need to see and choose, and working with engineering on trigger conditions before features reach the build phase.
Help evolve Caseware’s design system, raising the quality bar for component patterns and making sure AI-generated UI meets our design-system and accessibility standards before it reaches users.
Plan and lead user research, using AI to synthesize findings and surface patterns across usability testing sessions, so insights reach the team quickly and in a usable form.
Lead the cross-functional design conversations that shape product direction, driving the dialogue around end-user and business requirements with Product and Engineering, and using AI-generated prototypes to model scenarios rapidly and validate assumptions before the team commits.
Represent the team to Team Leads, Development, Product, Industry contacts, and other external stakeholders, and drive cross-team initiatives that require sustained collaboration across multiple product areas.
Develop the design team, mentoring junior and intermediate designers through hard design problems and decision-making under ambiguity, and helping them grow in both design craft and AI-assisted practice.
Participate actively in design critiques, and stay curious about where UX practice, AI tooling, and the accounting software industry are heading.