Staff UX Designer

We are looking for a Staff UX Designer who is ready to take on our hardest design problems and work at the intersection of design craft and AI-assisted making. At Caseware, our UX Design Team is actively transforming how design work gets done, integrating tools like Figma Make, Claude Code, and Replit into everyday practice. In this role, you will help define what that evolution looks like while designing user experiences for our cloud-based audit, financial reporting, and data analytics solutions used by accounting professionals in over 130 countries.

You will work closely with the Product, Engineering, and Design Teams, and with Design leadership, to set the standards and shape the experiences that help accounting and audit professionals navigate complex, regulated work with confidence and clarity.

This is a full-time permanent position

Location: This is a hybrid role requiring the successful candidate to work 3 days a week in our Toronto office located at 351 King St E Suite 1100 Toronto ON.

What you will be doing:

• • Own the design of Caseware’s most complex and ambiguous product areas across audit, financial reporting, and data analytics, taking work from problem framing through to implementation, and set the direction and documentation that other designers build on.

  • Design AI-native interaction patterns, including agentic-driven and conversational UI, intelligent defaults, and predictive interfaces, deciding how much the system should infer and when it should ask.

  • Design the human oversight moments inside agentic workflows so an auditor stays in control of work they are accountable for, setting the Caseware pattern by designing against over-trust rather than only for confirmation UX.

  • Think in whole auditor journeys rather than individual features, shaping how AI and agentic capabilities change the way audit work gets planned, executed, and reviewed.

  • Produce working prototypes that engineering can build directly from rather than static mockups, using AI to close the distance between designing and building, and to pressure-test assumptions before the team commits.

  • Decide which research questions are worth answering, and lead the studies that resolve real strategic uncertainty, using AI to synthesize findings and surface patterns quickly.

  • Shape what gets built before the scope is set, bringing design into roadmap and sequencing conversations with Product and Engineering, and turning high-level requirements into work the team can act on.

  • Lead cross-team design initiatives that no single team owns, spotting the critical risks early and building agreement without formal authority.

  • Contribute to Caseware’s design system and raise the quality bar for how AI-assisted work reaches users, making sure generated output meets our component and accessibility standards before it ships.

  • Mentor designers at any level of experience through their hardest problems, and turn what you work out together into practices the whole team can reuse.

  • Participate actively in design critiques, and stay curious about where UX practice, AI tooling, and the accounting software industry are heading.

What you will bring:

• Eight or more years of experience in user experience or related fields, with a portfolio built on depth: complex product problems, the design decisions you made under ambiguity, and the direction others built on.

• A track record of designing at the journey level in complex, regulated, or data-heavy domains, where the hard part is making expert work legible.

• A genuine enthusiasm for working at the intersection of design craft and AI-assisted making, and the judgment to keep speed and automation from compromising user-centred outcomes.

• Familiarity with AI-assisted design tools and processes, and the appetite to go further with them. We use Figma Make, Claude Code, and Replit, and we care more about how you evaluate and refine generated output than about which tools you have already used.

• Experience designing AI-native interaction patterns, such as conversational or predictive interfaces, or a clear point of view on designing for transparency, accountability, and user trust.

• Experience owning the research agenda for a product area and leading the studies that answer it.

• Proficiency with Figma, experience contributing to a component-based design system, and enough command of accessibility standards to judge whether AI-generated components meet them.

• Confidence setting design direction with Product and Engineering leadership early enough to shape scope, and a track record of mentoring experienced designers, not only those early in their careers.

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

The Tech Stack you will be working with:

• Figma, Replit and Claude Code for UI/UX design and prototyping

• Design systems implementation and management

• Angular UI framework and components (for implementation reference)

• User research and testing platforms

• Collaboration tools including Microsoft Teams, Jira, and Confluence