Senior UX Designer

📍 Job Overview

Job Title: Senior UX Designer

Company: Caseware

Location: Toronto, ON, Canada

Job Type: Full Time - Permanent

Category: User Experience (UX) Design

Date Posted: 2026-08-07

Experience Level: 3+ Years

Remote Status: Fully Remote (Canada)

🚀 Role Summary

• Spearhead the design of cutting-edge, cloud-based audit, financial reporting, and data analytics solutions, integrating AI-assisted tools into the end-to-end design process.

• Champion the adoption and evolution of AI in design practices, ensuring design judgment remains central while leveraging tools like Figma Make, Claude Code, and Replit.

• Design critical human oversight moments within agentic workflows, defining user interactions, triggers, and decision points for AI-driven features.

• Elevate Caseware's design system by ensuring AI-generated UI components meet established standards for quality, consistency, and accessibility.

• Lead user research initiatives, utilizing AI for efficient synthesis of findings and pattern identification to accelerate insight delivery.

• Drive cross-functional collaboration with Product and Engineering teams, shaping product direction through informed design conversations and rapid prototyping.

• Mentor and develop junior and intermediate designers, guiding them through complex design challenges and ambiguity in both traditional and AI-assisted design contexts.

📈 Primary Responsibilities

• Design exceptional user experiences for Caseware’s suite of cloud-based audit, financial reporting, and data analytics products, from initial problem framing through to implementation, leveraging a modern toolkit that pairs Figma Make, Claude Code, and Replit with traditional UX methods.

• Shape and evolve how the design team integrates AI into its daily practice, actively evaluating new tools, sharing best practices, and maintaining a fluid transition between AI-assisted and manual design modes.

• Develop designs for human oversight within agentic workflows, meticulously defining what users need to see and choose, and collaborating with engineering on trigger conditions before feature development.

• Contribute to the evolution of Caseware’s design system, raising the quality bar for component patterns and ensuring AI-generated UI consistently meets design system and accessibility standards.

• Plan and lead end-to-end user research programs, employing AI to synthesize findings and surface patterns from usability testing sessions, ensuring rapid and usable insights reach the team.

• Lead cross-functional design conversations that influence product direction, fostering dialogue around end-user and business requirements with Product and Engineering, and utilizing AI-generated prototypes for rapid scenario modeling and assumption validation.

• Represent the design team to senior stakeholders, including Team Leads, Development, Product leadership, and external partners, driving cross-team initiatives that demand sustained collaboration across multiple product areas.

• Mentor junior and intermediate designers, guiding them through complex design problems and decision-making processes in ambiguous situations, and supporting their growth in both design craft and AI-assisted practice.

• Actively participate in design critiques and maintain a curious mindset regarding advancements in UX practice, AI tooling, and the accounting software industry.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong foundation in design principles, human-computer interaction, or a related field is expected. A portfolio demonstrating practical application of these principles is paramount.

Experience: A minimum of 3 years of professional UX design experience is required, with a proven track record of leading design initiatives and mentoring other designers.

Required Skills:

• A genuine enthusiasm for the intersection of design craft and AI-assisted making, coupled with an understanding of responsible AI principles (bias, transparency, accountability, designing for trust) and critical thinking to balance speed and user-centricity.

• Portfolio showcasing not just design output but also leadership in guiding others through complex problems and decision-making under ambiguity.

• Fluency with AI-assisted tools such as Figma Make, Claude Code, and Replit, including effective prompting, custom workflow creation, output evaluation, and refinement to meet design system and accessibility standards.

• Design experience with, or a clear perspective on, human oversight in agentic or AI-driven features, including considerations for accountability, transparency, and user control.

• Experience planning and leading comprehensive user research programs, including the application of AI for synthesizing findings and identifying patterns from usability testing.

• Proficiency with Figma and other related design and prototyping tools.

• Substantial experience working within and contributing to a component-based design system.

• Strong working knowledge of accessibility standards (e.g., WCAG), including the ability to evaluate AI-generated components for compliance and usability gaps.

• Confidence in representing design direction to senior stakeholders and driving cross-team initiatives through influence and consensus-building.

• Experience mentoring junior or intermediate designers, providing constructive feedback and fostering their growth.

• Excellent communication skills for facilitating design discussions and presenting design reasoning to diverse audiences. Preferred Skills:

• Knowledge of the accounting, audit, or financial services industries.

• Prior experience designing for AI-powered or conversational product features.

📝 Enhancement Note: The requirement for AI-assisted tool fluency (Figma Make, Claude Code, Replit) is a significant differentiator for this role, indicating Caseware's commitment to innovative design practices. Candidates should highlight projects where they've experimented with or integrated AI into their workflow, even if in an experimental capacity.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Demonstrate a minimum of 3 years of impactful UX design work, showcasing a clear progression from problem identification to user-centered solutions.

• Include case studies that highlight your leadership in navigating ambiguous design challenges and guiding team members through complex problem-solving processes.

• Present examples of how you have contributed to or evolved a component-based design system, emphasizing consistency, scalability, and adherence to standards.

• Showcase your approach to user research, including methodologies used, AI synthesis techniques if applicable, and how insights directly influenced design decisions.

• Provide evidence of your understanding and application of accessibility standards in your designs, particularly in evaluating AI-generated outputs.

• Illustrate your experience with AI-assisted design tools, detailing your approach to prompting, workflow creation, and refining AI-generated outputs for production readiness. Process Documentation:

• Detail your process for translating complex user needs and business requirements into intuitive and effective user experiences, particularly in the context of regulated financial software.

• Describe your methodology for integrating AI tools into the design lifecycle, including how you manage the balance between AI-generated output and human design oversight.

• Outline your approach to user research, from planning and execution to synthesizing findings with AI assistance and communicating actionable insights to cross-functional teams.

• Illustrate your process for contributing to and maintaining design systems, ensuring alignment with accessibility standards and AI-generated component quality.

📝 Enhancement Note: The emphasis on "leading others through the problem" and "making design decisions under ambiguity" in the portfolio requirements indicates a need for candidates to demonstrate not just execution skills but also strategic thinking, problem-solving acumen, and leadership potential within the design team.

💵 Compensation & Benefits

Salary Range: $105,000 CAD - $115,000 CAD per year.

• This range is determined based on factors including transferable skills, relevant experience, market conditions, and the candidate's primary work location within Canada.

• The posted range is subject to change and may be updated periodically. Benefits:

• Discretionary Bonus/Commission: Eligibility for performance-based bonuses or commissions.

• Comprehensive Health Insurance: Coverage for medical, dental, and vision needs.

• Retirement Plans: Support for long-term financial planning.

• Flexible Work Options: Adaptable work arrangements to support personal needs.

• Remote Opportunities: Full remote work capability for candidates legally authorized to work in Canada.

• Generous Time-Off Policies: Ample paid time off to promote work-life balance.

• Career Growth Opportunities: Structured pathways and support for professional development and advancement.

• Recognition Programs: Formal and informal recognition for hard work and achievements.

Working Hours: Approximately 40 hours per week, with flexibility offered to support work-life balance.

📝 Enhancement Note: The provided salary range is specific to the Canadian market. For candidates outside of Canada considering relocation, a cost of living adjustment would be necessary for accurate compensation comparison. The inclusion of a discretionary bonus/commission alongside base salary suggests a performance-driven compensation structure.

🎯 Team & Company Context

🏢 Company Culture

Industry: Fintech (Financial Technology), specializing in Audit & Accounting Software. Caseware is a recognized leader with over 30 years of experience, serving over 500,000 users globally.

Company Size: While not explicitly stated, Caseware's global reach (130+ countries, 36,000+ users listing the skill on LinkedIn) suggests a medium to large enterprise with established operations and a significant market presence. The recent investment from Hg Capital in 2020 indicates a phase of accelerated growth.

Founded: Over 30 years ago, positioning Caseware as an established player with deep domain expertise in its sector.

Team Structure:

• The UX Design Team is described as actively transforming its work practices, integrating AI tools and modern methodologies. This suggests a forward-thinking, innovative team environment.

• This role involves close collaboration with Product, Engineering, and potentially other Design Teams, indicating a cross-functional and integrated product development approach.

• The Senior UX Designer will mentor junior and intermediate designers, implying a tiered structure within the design team that supports skill development and knowledge sharing. Methodology:

• AI-Assisted Design: A core methodology involves integrating tools like Figma Make, Claude Code, and Replit into daily design workflows to enhance efficiency and innovation.

• User-Centered Design: Despite AI integration, the role emphasizes design judgment, user needs, and ensuring AI-generated outputs meet user-centric outcomes and accessibility standards.

• Agile/Iterative Development: The process involves moving features from problem framing through to implementation, suggesting iterative development cycles with feedback loops from user research and cross-functional teams.

• Design System Evolution: A commitment to maintaining and evolving a robust design system is a key operational principle.

Company Website: https://www.caseware.com/

📝 Enhancement Note: Caseware's positioning as a "Canada's original Fintech companies" and its global reach highlight its established presence and influence. The emphasis on AI integration is a significant cultural and operational differentiator, suggesting a company that embraces technological advancement and modern work practices.

📈 Career & Growth Analysis

Operations Career Level: Senior UX Designer. This level indicates a position of significant responsibility, requiring not only expert-level design skills but also the ability to lead initiatives, mentor others, and influence product strategy. It sits above intermediate designers and contributes to the strategic direction of UX practices within the company.

Reporting Structure: The role involves representing the design team to Team Leads and Product leadership, suggesting a reporting line that likely goes through a Design Manager or Head of Design, with direct interaction and collaboration with Product Managers and Engineering Leads.

Operations Impact: The Senior UX Designer's work directly impacts the usability, efficiency, and adoption of Caseware's core audit, financial reporting, and data analytics solutions. By improving user experiences and integrating innovative AI capabilities, they contribute to enhanced productivity for accounting professionals worldwide, directly influencing client success and Caseware's market competitiveness.

Growth Opportunities:

• Leadership in AI Design: Become a key figure in shaping and advancing Caseware's use of AI in design, potentially leading new initiatives or defining best practices for AI integration.

• Design System Ownership: Take a more prominent role in the strategic direction and evolution of Caseware's design system, influencing its architecture and adoption across products.

• Mentorship and Team Development: Expand mentorship responsibilities, potentially contributing to the formal training and development programs for the design team.

• Strategic Product Influence: Deepen influence on product strategy by leading design-thinking workshops, driving user research insights, and championing user-centered approaches in complex, regulated domains.

• Industry Expertise: Develop specialized knowledge in fintech, audit, and financial reporting software, becoming a subject matter expert in a critical industry.

📝 Enhancement Note: The emphasis on mentoring and shaping AI design practices suggests a growth path that could lead to Design Lead or Principal Designer roles, with a focus on both technical expertise and team leadership.

🌐 Work Environment

Office Type: Fully Remote. This allows for a flexible work environment, open to candidates legally authorized to work in Canada.

Office Location(s): While the role is remote, the company headquarters is in Toronto, ON, Canada. This indicates potential for occasional in-person collaboration or team events if desired or organized, though not a requirement.

Workspace Context:

• Collaborative Environment: The role emphasizes close collaboration with Product, Engineering, and other designers, facilitated through digital tools and communication platforms.

• Technology-Rich: Expect access to modern design and AI tools, including Figma, Claude Code, Replit, and potentially others, to support innovative design processes.

• Global Interaction: Opportunities to collaborate with a diverse, global team, exposing the designer to different markets and user needs.

Work Schedule: The standard work week is approximately 40 hours, with flexibility offered to support work-life balance. This allows for effective time management to engage in design work, user research, and cross-functional meetings.

📝 Enhancement Note: The fully remote nature of the role requires strong self-discipline, proactive communication, and proficiency with remote collaboration tools. Candidates should be prepared to articulate how they maintain productivity and collaboration in a distributed setting.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your application and portfolio to assess alignment with the role's requirements, particularly experience with AI tools and design leadership.

• Hiring Manager/Team Interview: A discussion focusing on your experience, design philosophy, approach to AI in design, and how you handle ambiguity. Expect questions about your portfolio case studies.

• Design Challenge/Workshop: A practical exercise to evaluate your design thinking, problem-solving skills, and ability to apply AI tools. This may involve designing a feature, critiquing an existing design, or presenting a solution to a hypothetical problem.

• Cross-Functional Interview: Meeting with members of the Product and Engineering teams to assess collaboration style, communication skills, and ability to translate user needs into technical requirements.

• Final Interview: Potentially with senior leadership to discuss strategic fit, leadership potential, and overall alignment with Caseware's culture and vision.

Portfolio Review Tips:

• Focus on AI Integration: Clearly articulate your experience with AI-assisted tools (Figma Make, Claude Code, Replit). Detail how you prompted, evaluated, and refined AI outputs.

• Showcase Leadership & Ambiguity: Select case studies that demonstrate your ability to lead design processes, mentor others, and navigate complex, uncertain problem spaces. Highlight decision-making rationale.

• Design System Contributions: Include examples of your work with design systems, showing how you maintained consistency, improved components, and ensured accessibility, especially for AI-generated elements.

• Research Methodology: Present your user research process, emphasizing how you synthesized findings (potentially with AI) and translated them into actionable design improvements.

• Storytelling: Structure your case studies as narratives, explaining the problem, your process, the challenges faced, your solutions, and the impact of your work. Quantify results where possible.

• Accessibility & Responsible AI: Ensure your portfolio explicitly addresses how you consider accessibility and responsible AI principles in your design work.

Challenge Preparation:

• AI Tool Familiarity: Be prepared to demonstrate or discuss your proficiency with Figma Make, Claude Code, and Replit. Understand their capabilities and limitations.

• Problem Framing: Practice breaking down complex problems into smaller, manageable parts, especially those involving AI and human oversight.

• Design System Thinking: Be ready to discuss how you would extend or apply an existing design system to new features, particularly those influenced by AI.

• Stakeholder Communication: Prepare to explain your design decisions clearly and concisely, justifying your choices to both technical and non-technical audiences.

• Accessibility & Ethics: Anticipate questions related to ethical AI design, bias mitigation, and ensuring inclusivity and accessibility in AI-driven features.

📝 Enhancement Note: Given the emphasis on AI, candidates should be prepared to discuss their philosophy on responsible AI and how they ensure user-centricity and ethical considerations are maintained when leveraging AI tools.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: Core tool for UI design, prototyping, and collaboration. Proficiency expected in advanced features, component creation, and design system integration.

• Figma Make: Specific AI-assisted design tool for generating UI elements and workflows.

• Claude Code: AI assistant for code generation and potentially design logic.

• Replit: Cloud-based IDE for coding and development, likely used for prototyping or integrating AI-generated code.

• Prototyping Tools: Proficiency with Figma's prototyping capabilities and potentially other tools for richer interactive prototypes.

Analytics & Reporting:

• User Research Platforms: Tools for conducting usability testing, gathering feedback, and potentially AI-powered synthesis (e.g., UserTesting.com, Dovetail, or internal tools).

• Analytics Tools: While not explicitly mentioned for UX, understanding how product analytics (e.g., Amplitude, Google Analytics) inform design decisions is beneficial.

CRM & Automation:

• Not directly applicable to the UX Designer role, but an understanding of how design outputs feed into product development pipelines (e.g., Jira, Confluence) is useful.

📝 Enhancement Note: The explicit mention of Figma Make, Claude Code, and Replit highlights Caseware's commitment to integrating cutting-edge AI tools into their design workflow. Candidates should be prepared to demonstrate practical experience or a strong understanding of how these tools can be leveraged effectively.

👥 Team Culture & Values

Operations Values:

• Innovation: A core value driving the integration of cutting-edge technology like AI into design and product development.

• Collaboration (Many Voices, One Team): Emphasis on teamwork, knowledge sharing, and collective contribution to achieve shared goals.

• Customer Focus: Building technology that directly addresses the needs of accounting professionals and drives their success.

• Impactful Work: Contributing to solutions that shape the future of audits, financial reporting, and data analytics.

• Efficiency & Speed: Leveraging AI and modern tools to accelerate design processes and deliver value quickly.

• Inclusivity & Equity: Dedicated to building diverse teams and fostering an equitable and inclusive environment.

Collaboration Style:

• Cross-Functional Integration: Close working relationships with Product and Engineering are essential, requiring clear communication and a shared understanding of project goals.

• Design Critique Culture: Active participation in design critiques to provide and receive constructive feedback, fostering continuous improvement.

• Knowledge Sharing: Encouragement to share insights, best practices, and learnings, particularly around AI tool adoption and UX methodologies.

• Proactive Communication: Given the remote nature, proactive and clear communication through digital channels is critical for effective collaboration.

📝 Enhancement Note: The "Many Voices, One Team" value, coupled with the emphasis on inclusivity, suggests a culture that highly values diverse perspectives and collaborative problem-solving. Candidates should be ready to share examples of how they contribute to a positive and inclusive team environment.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing AI Efficiency with Design Craft: Ensuring that the speed and automation offered by AI tools do not compromise the quality, creativity, and user-centricity of designs. Requires critical evaluation and refinement of AI outputs.

• Designing for Human Oversight in Agentic Systems: Creating intuitive and effective user experiences for moments where users need to intervene, control, or validate AI actions, ensuring trust and accountability.

• Integrating AI into Established Design Systems: Adapting and extending existing design systems to accommodate AI-generated components and workflows while maintaining consistency and accessibility.

• Driving Adoption of New Tools/Methodologies: Championing the use of new AI design tools and evolving design practices within the team and across product development.

• Mentoring in Ambiguous AI Contexts: Guiding junior designers through the complexities of AI-assisted design and decision-making in rapidly evolving technological landscapes.

Learning & Development Opportunities:

• AI in Design Specialization: Deepen expertise in leveraging AI tools for UX design, becoming a go-to resource for best practices and innovative applications.

• Advanced UX Leadership: Develop strategic leadership skills through mentoring, cross-functional initiative leadership, and influencing product roadmaps.

• Fintech Domain Expertise: Gain in-depth knowledge of the accounting, audit, and financial reporting industries, understanding the unique user needs and regulatory environments.

• Design System Strategy: Contribute to the strategic evolution of design systems, potentially influencing their architecture and governance.

• Industry Conferences & Training: Opportunities to attend relevant UX, AI, and fintech conferences or pursue certifications to stay abreast of industry trends.

📝 Enhancement Note: The challenges presented are directly tied to the innovative nature of the role. Candidates who thrive in environments that push technological boundaries and require continuous learning will be well-suited.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to balance AI-generated output with your own design judgment to achieve a user-centered outcome. What was your process?" (Focus: Critical thinking, AI evaluation, user-centricity)

• "How would you approach designing the 'human oversight' moments in an AI-driven workflow for an accounting professional? What are the key considerations for trust and accountability?" (Focus: Agentic design, ethical AI, user control)

• "Walk us through a complex design problem you led a team through. How did you facilitate decision-making under ambiguity and mentor junior designers?" (Focus: Leadership, mentorship, ambiguity resolution) Company & Culture Questions:

• "What interests you about Caseware's mission and its position in the fintech industry, particularly regarding AI integration?" (Focus: Company research, strategic alignment)

• "How do you see yourself contributing to a 'Many Voices, One Team' culture, especially in a remote environment?" (Focus: Collaboration, inclusivity, remote work)

• "How do you stay current with advancements in UX, AI tooling, and the accounting software industry?" (Focus: Continuous learning, industry awareness) Portfolio Presentation Strategy:

• AI Integration Showcase: Dedicate time to explaining your process with Figma Make, Claude Code, or Replit. Show how you used them, the prompts, the iterations, and the final refinements.

• Highlight Leadership & Mentorship: For case studies, clearly delineate your role in leading the project, guiding other designers, and making key strategic decisions.

• Quantify Impact: Whenever possible, present metrics or outcomes that demonstrate the success of your designs (e.g., improved usability scores, increased adoption, reduced errors).

• Design System & Accessibility Focus: Explicitly discuss your contributions to design systems and how you ensure accessibility, especially when working with AI-generated components.

• Interactive Elements: If possible, use interactive prototypes or live demos to showcase your work, making the presentation more engaging.

📝 Enhancement Note: Candidates should prepare to discuss specific examples of how they've used AI in their design process, even if it was experimental or for personal projects, demonstrating initiative and forward-thinking.

📌 Application Steps

To apply for this Senior UX Designer position:

• Submit your application through the provided link on jobs.lever.co.

• Tailor your Resume: Highlight experience with AI-assisted design tools (Figma Make, Claude Code, Replit), user research leadership, design system contributions, and mentorship. Use keywords from the job description.

• Curate Your Portfolio: Select 2-3 strong case studies that best showcase your ability to lead complex design problems, integrate AI tools, champion design systems, and mentor others. Ensure clear articulation of your process, challenges, and impact.

• Prepare for AI Discussions: Be ready to discuss your understanding of responsible AI, your experience with AI design tools, and your vision for how AI can enhance UX design.

• Research Caseware: Understand their products, market position, and company values to articulate your interest and cultural fit.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.