Senior UX Designer

📍 Job Overview

Job Title: Senior UX Designer

Company: Caseware

Location: Toronto, ON, Canada

Job Type: Full Time - Permanent

Category: Product Design / User Experience

Date Posted: 2026-06-25

Experience Level: Mid-Senior Level (3-5 years)

Remote Status: Hybrid (3 days in office)

🚀 Role Summary

• Design cutting-edge user experiences for Caseware's cloud-based audit, financial reporting, and data analytics solutions, leveraging a modern toolkit that integrates AI-assisted tools like Figma Make, Claude Code, and Replit with established UX methodologies.

• Champion the integration of AI into everyday design practices, evaluating emerging tools, fostering knowledge sharing, and ensuring design judgment remains central to all decisions.

• Develop user-centered design solutions for complex, regulated workflows, focusing on clarity, confidence, and efficiency for accounting and audit professionals globally.

• Lead user research initiatives, utilizing AI for efficient synthesis of findings, to inform product strategy and design iterations.

📝 Enhancement Note: This role is positioned as a Senior UX Designer with a significant emphasis on integrating AI-assisted tools into the design process. The "Senior" title implies leadership in design thinking, problem-solving, and mentorship, while the AI focus indicates a forward-thinking approach to design operations and product development. The target audience for this role is experienced UX professionals who are not only proficient in traditional design craft but are also keen on exploring and implementing generative AI in their workflow.

📈 Primary Responsibilities

• Design end-to-end user experiences for Caseware's suite of financial software, from initial problem framing through to implementation, utilizing a blend of traditional UX methods and AI-assisted tools like Figma Make, Claude Code, and Replit.

• Actively shape and evolve the team's approach to AI-assisted design, experimenting with new tools, sharing best practices, and ensuring a seamless transition between AI-generated outputs and manual design refinement.

• Design critical human oversight moments within AI-driven workflows, defining necessary user inputs, decision points, and trigger conditions in collaboration with engineering teams.

• Contribute to the evolution and maintenance of Caseware's design system, ensuring AI-generated UI components meet established standards for quality, consistency, and accessibility.

• Plan and lead comprehensive user research programs, leveraging AI tools to synthesize research findings and identify key patterns to accelerate insight delivery to product and engineering teams.

• Facilitate cross-functional design discussions that influence product strategy, effectively communicating end-user needs and business requirements to Product and Engineering stakeholders, using AI-generated prototypes for rapid scenario modeling and validation.

• Represent the design team in discussions with Team Leads, Development, Product Management, and external industry contacts, driving multi-product initiatives that require sustained collaboration and consensus-building.

• Mentor and develop junior and intermediate designers by guiding them through complex design challenges, fostering decision-making in ambiguous situations, and supporting their growth in both design craft and AI-assisted practices.

• Actively participate in design critiques, staying abreast of advancements in UX practice, AI tooling, and the evolving landscape of accounting software.

📝 Enhancement Note: The responsibilities highlight a blend of individual contribution, strategic influence, and team development. The emphasis on "shaping how the team brings AI into its everyday design practice" and "designing the human oversight moments" points to a role that is not just about executing designs but also about pioneering new ways of working with AI in UX. The requirement to "mentor junior and intermediate designers" solidifies the "Senior" aspect of the role.

🎓 Skills & Qualifications

Education:

• While not explicitly stated, a Bachelor's or Master's degree in Human-Computer Interaction (HCI), Design, Computer Science, or a related field is typically expected for a Senior UX Designer role. Equivalent practical experience will also be considered. Experience:

• A minimum of 3 years of professional experience in User Experience (UX) design.

• Demonstrated experience in leading design initiatives and guiding teams through complex, ambiguous problem spaces.

• Proven ability to translate user needs and business objectives into effective, user-centered design solutions. Required Skills:

• AI-Assisted Design Fluency: Proficient with AI-assisted tools such as Figma Make, Claude Code, and Replit, including effective prompt engineering, custom workflow development, output evaluation, and refinement to meet design and accessibility standards.

• UX Design Craft: Strong command of UX design principles, methodologies, and best practices across the entire product development lifecycle, from research and ideation to prototyping and implementation.

• User Research Leadership: Experience in planning, conducting, and synthesizing user research (e.g., usability testing, interviews, surveys), with the ability to leverage AI for efficient analysis and pattern identification.

• Design Systems Expertise: Substantial experience working with and evolving component-based design systems, ensuring consistency, scalability, and adherence to accessibility standards.

• Prototyping & Wireframing: Proficiency with industry-standard design and prototyping tools, with a strong emphasis on Figma.

• Accessibility Standards: Deep understanding of WCAG and other relevant accessibility guidelines, with the ability to ensure AI-generated designs meet these standards.

• Problem-Solving & Ambiguity: Demonstrated ability to tackle complex design problems and make sound design decisions in ambiguous situations.

• Cross-functional Collaboration: Proven experience collaborating effectively with Product Managers, Engineers, and other stakeholders.

• Mentorship: Experience mentoring junior or intermediate designers, providing constructive feedback and guidance.

Preferred Skills:

• Knowledge or experience within the accounting, audit, or financial services industries.

• Prior experience designing for AI-powered features, conversational interfaces, or agentic workflows.

• Understanding of responsible AI principles (bias, transparency, accountability, designing for trust).

• Experience with strategy development and presenting design direction to senior leadership and external partners.

📝 Enhancement Note: The "Required Skills" section has been expanded to explicitly call out AI-assisted design tools and methodologies as core requirements, reflecting the job description's emphasis. The inclusion of "Responsible AI principles" is a crucial differentiator for this role. The portfolio requirement is also a key element, emphasizing the demonstration of leadership and decision-making under ambiguity.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A robust portfolio showcasing at least 3 years of professional UX design work, with a strong emphasis on demonstrating leadership in problem-solving and design decision-making, especially in ambiguous contexts.

• Case studies that detail the end-to-end design process, from problem framing and user research to ideation, prototyping, and implementation, highlighting your role and contributions.

• Specific examples of how you have leveraged AI-assisted tools (e.g., Figma Make, Claude Code, Replit) in your design workflow, detailing the benefits and any challenges encountered.

• Demonstrations of your ability to evolve or contribute to a component-based design system, including examples of how you ensure consistency and adherence to standards.

• Evidence of your work on user research programs, including how you synthesized findings (potentially with AI assistance) to drive design decisions.

• Examples of designs that adhere to accessibility standards, with clear explanations of how these standards were met, particularly for AI-generated components. Process Documentation:

• Projects that illustrate your ability to design for human oversight within AI-driven workflows, showing how you considered user control, transparency, and accountability.

• Documentation of how you have facilitated cross-functional design conversations, driving consensus and influencing product direction with Product and Engineering teams.

• Examples of how you have mentored junior designers, showcasing your approach to feedback, guidance, and skill development.

• Prototypes or case studies that demonstrate your ability to use AI-generated prototypes for rapid scenario modeling and validation of assumptions.

📝 Enhancement Note: The portfolio requirements are tailored to emphasize the unique aspects of this role, particularly the integration of AI tools, leadership in ambiguous situations, and contributions to design systems and responsible AI. The "Process Documentation" section focuses on the strategic and collaborative elements expected of a Senior Designer.

💵 Compensation & Benefits

Salary Range:

• The annual base salary for this position is between $105,000 CAD and $115,000 CAD.

• This range is determined by factors including transferable skills, relevant experience, market conditions, and primary work location.

• Actual compensation will be finalized during the hiring process. Benefits:

• Health Insurance: Comprehensive health coverage.

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

• Discretionary Bonus: Potential for performance-based bonuses.

• Commission: Applicable for certain roles, though less common for UX Designers, this may refer to team or company performance incentives.

• Flexible Work Options: Encourages work-life balance.

• Generous Time-Off Policies: Ample paid time off.

• Recognition Programs: Formal and informal recognition for contributions.

• Performance Bonuses: Additional bonuses tied to individual or team performance.

• Global Opportunities: Exposure to international projects and diverse teams.

Working Hours:

• Standard full-time hours, approximately 40 hours per week, with flexibility offered to support work-life balance.

📝 Enhancement Note: The salary range is provided as specified. The benefits list has been structured for clarity, highlighting key offerings relevant to a professional role. The note about commission for a UX role is a slight anomaly but included as per the source data; it might reflect a broader company incentive structure. The "Working Hours" section acknowledges the standard but also reflects the company's stated commitment to flexibility.

🎯 Team & Company Context

🏢 Company Culture

Industry: Fintech / Software Development (Audit & Accounting Software)

Company Size: Caseware is a well-established company with over 30 years in the industry, serving over 500,000 users across 130 countries. While the exact employee count isn't provided, its global reach and established user base suggest a medium to large-sized organization with significant operational depth.

Founded: Over 30 years ago, indicating a long-standing presence and expertise in the audit and accounting software market.

Team Structure:

• The UX Design team is integrated within Product Development, working closely with Product Managers and Engineering teams.

• This role involves collaboration across multiple product areas and requires driving initiatives without formal authority, suggesting a collaborative, matrixed organizational structure.

• The team is actively exploring and integrating cutting-edge AI tools into its design processes, indicating a culture of innovation and continuous learning within the design function. Methodology:

• The team utilizes a modern toolkit that blends traditional UX methods with AI-assisted tools like Figma Make, Claude Code, and Replit, emphasizing efficiency and innovation.

• A strong focus is placed on user-centered design, ensuring that user needs and business requirements are met through thoughtful design solutions.

• Design system development and maintenance are integral to ensuring consistency and quality across products, with an emphasis on accessibility.

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

📝 Enhancement Note: The company culture is characterized by innovation, particularly in its embrace of AI in design. The emphasis on "Many Voices, One Team" and diversity/inclusion suggests a collaborative and equitable environment. The context of Fintech and accounting software highlights the regulated and critical nature of the products designed.

📈 Career & Growth Analysis

Operations Career Level: This role is a "Senior UX Designer," indicating a mid-to-senior level position. It requires not only strong individual design capabilities but also leadership, mentorship, and the ability to influence product direction and team practices. The role involves taking ownership of complex design problems and shaping new ways of working, particularly with AI.

Reporting Structure: While not explicitly detailed, the Senior UX Designer will likely report to a UX Lead, Design Manager, or Head of Product Design. They will work closely with Product Managers and Engineering Leads on specific product initiatives.

Operations Impact: The UX Designer's work directly impacts the usability, efficiency, and adoption of Caseware's core products (audit, financial reporting, data analytics) used by thousands of accounting and audit professionals worldwide. By improving user experience, they contribute to client confidence, operational efficiency, and the overall success and competitiveness of Caseware's software solutions in a critical industry.

Growth Opportunities:

• Design Leadership: Potential to grow into a Lead UX Designer or Design Manager role, taking on more strategic responsibilities and managing a team.

• AI Specialization: Opportunity to become a subject matter expert in AI-assisted design within the company, potentially leading initiatives or training programs.

• Product Strategy Influence: Deeper involvement in shaping product roadmaps and long-term UX strategy.

• Skill Development: Continuous learning in UX best practices, emerging AI technologies, and the financial services industry.

• Cross-functional Advancement: Potential to move into Product Management or related roles by leveraging deep product understanding.

📝 Enhancement Note: The "Operations Impact" section is reframed to focus on "Product Impact" given the nature of the role. The growth opportunities are tailored to a Senior UX Designer, emphasizing leadership, AI specialization, and strategic influence.

🌐 Work Environment

Office Type: Hybrid role, requiring 3 days per week in the Toronto office. This suggests a modern office environment designed for collaboration and focused work, balancing in-person interaction with remote flexibility.

Office Location(s): 351 King St E Suite 1100, Toronto, ON. This location is in a prominent business district, likely offering good accessibility.

Workspace Context:

• The office environment is expected to be conducive to collaboration, with opportunities to interact with Product, Engineering, and fellow Design team members.

• Access to necessary design tools and technology, including advanced AI-assisted software, will be provided.

• The hybrid model allows for focused individual work at home and collaborative sessions, brainstorming, and team building in the office. Work Schedule:

• Standard full-time employment (approximately 40 hours/week) with a commitment to work-life balance, offering flexible work options. The hybrid requirement means specific days will be spent in the Toronto office.

📝 Enhancement Note: The "Workspace Context" emphasizes the blend of collaborative opportunities and focused work enabled by the hybrid model and the company's approach to technology.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Review of resume and portfolio to assess experience, skills, and alignment with the role's AI and leadership focus.

• Portfolio Presentation & Design Challenge: Candidates will likely present their portfolio, discussing key projects, their design process, leadership contributions, and how they've utilized AI tools. A design exercise or case study related to solving a complex problem within the financial software domain, potentially involving AI considerations, may be assigned.

• Cross-functional Interviews: Meetings with Product Managers, Engineering Leads, and potentially other designers to assess collaboration skills, technical understanding, and cultural fit.

• Team Lead/Hiring Manager Interview: Final discussion focusing on strategic thinking, mentorship capabilities, and overall fit with the team's vision and Caseware's values.

Portfolio Review Tips:

• Highlight AI Integration: Clearly showcase projects where you've used AI-assisted tools (Figma Make, Claude Code, Replit), detailing your prompts, how you evaluated outputs, and how you refined them.

• Demonstrate Leadership & Ambiguity: Select case studies that exemplify your ability to lead design efforts, navigate complex problems, and make decisions under uncertainty. Focus on your thought process and rationale.

• Showcase Design System Contributions: If applicable, detail your involvement in creating, evolving, or maintaining a design system, emphasizing consistency and accessibility.

• Detail User Research Impact: Explain how your user research insights (and any AI synthesis methods used) directly influenced design outcomes and product strategy.

• Tell a Story: Structure your case studies with a clear narrative: problem, your role, process, solutions, outcomes, and learnings.

• Address Responsible AI: Be prepared to discuss your understanding of responsible AI principles and how you apply them in your design work.

Challenge Preparation:

• Understand the Domain: Familiarize yourself with the challenges and needs of accounting and audit professionals. Research Caseware's existing products and market position.

• AI Scenario Thinking: Practice designing solutions that involve human oversight in AI-driven workflows. Consider ethical implications, bias, transparency, and user control.

• Design System Application: Be ready to discuss how you would apply or evolve a design system, especially if AI generates new components.

• Communication & Mentorship: Prepare examples of how you communicate design decisions to non-designers and how you mentor junior team members.

📝 Enhancement Note: The interview and portfolio advice is specifically geared towards the unique requirements of this role, emphasizing AI proficiency, leadership, and domain relevance.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: Core tool for design, prototyping, and collaboration. Proficiency with Figma Make (AI integration) is a key requirement.

• AI Coding Assistants: Claude Code, Replit (or similar AI tools for code generation/assistance).

• Prototyping Tools: Figma, and potentially others for advanced or specific use cases.

• Design System Tools: Figma Libraries, Storybook (potential, for component documentation).

Analytics & Reporting:

• While not a primary focus for UX, familiarity with product analytics tools (e.g., Amplitude, Mixpanel, Google Analytics) for understanding user behavior and measuring impact is beneficial.

• Proficiency in presenting data and insights to inform design decisions. CRM & Automation:

• Not directly applicable to the UX Designer role, but understanding how design integrates with product management and engineering workflows is essential.

• Familiarity with project management tools like Jira, Confluence, or Asana for tracking design tasks and collaborating with development teams.

📝 Enhancement Note: This section highlights the specific AI tools mentioned in the job description (Figma Make, Claude Code, Replit) as primary requirements, alongside traditional design tools like Figma.

👥 Team Culture & Values

Operations Values:

• Innovation & Forward-Thinking: Valuing the exploration and integration of new technologies like AI to enhance design processes and product capabilities.

• Collaboration & Teamwork: Emphasizing a "Many Voices, One Team" approach, fostering a supportive environment where diverse perspectives are welcomed and integrated.

• User-Centricity: A deep commitment to understanding and serving the needs of accounting and audit professionals, ensuring products are intuitive and effective.

• Excellence & Quality: Striving for high standards in design craft, component quality, and accessibility, ensuring AI-generated outputs meet rigorous criteria.

• Continuous Learning: Encouraging curiosity and ongoing development in UX practices, AI tooling, and industry trends.

Collaboration Style:

• Cross-Functional Integration: Working closely with Product Management and Engineering to shape product direction, requiring strong communication and consensus-building skills.

• Design Critiques & Feedback: An active culture of design critiques to ensure quality, share knowledge, and foster collective improvement.

• Mentorship & Knowledge Sharing: A commitment to developing team members, with senior designers mentoring junior colleagues and sharing insights on AI-assisted practices.

📝 Enhancement Note: The "Operations Values" are derived from the company's stated values and the role's emphasis on innovation, collaboration, and excellence. The "Collaboration Style" reflects the cross-functional nature of product development and the team's approach to continuous improvement.

⚡ Challenges & Growth Opportunities

Challenges:

• Navigating AI Integration: Balancing the speed and efficiency gains from AI tools with the need for design judgment, responsible AI principles, and maintaining user-centered outcomes. Ensuring AI-generated outputs meet high standards for quality and accessibility.

• Designing for Regulated Industries: Creating intuitive user experiences for complex, highly regulated workflows in audit and financial reporting, where precision and compliance are paramount.

• Human Oversight in Agentic Workflows: Designing effective and trustworthy human-AI interaction points, defining appropriate levels of user control and oversight.

• Cross-Team Alignment: Driving consensus and initiatives across multiple product teams and stakeholders without direct authority.

• Mentoring & Development: Effectively guiding and developing junior designers, particularly in the rapidly evolving landscape of AI-assisted design.

Learning & Development Opportunities:

• AI Tool Mastery: Deepen expertise in cutting-edge AI tools for design, becoming a go-to resource for the team.

• Industry Specialization: Gain in-depth knowledge of the audit, accounting, and financial reporting sectors.

• Leadership Skills: Develop strategic leadership capabilities through mentorship and cross-functional project ownership.

• Design System Evolution: Contribute to the strategic direction and advancement of Caseware's design system.

• Industry Trends: Stay ahead of UX best practices, AI advancements, and Fintech innovations through conferences, workshops, and continuous self-study.

📝 Enhancement Note: The challenges are framed around the core aspects of the role, particularly the AI integration and the specific industry context. Growth opportunities are aligned with career progression for a Senior UX Designer.

💡 Interview Preparation

Strategy Questions:

• "Describe a complex design problem you faced where you had to make critical decisions under ambiguity. How did you approach it, and what was the outcome?" (Focus on your thought process, leadership, and how you used data/research.)

• "How would you integrate AI-assisted tools like Figma Make or Claude Code into a typical design workflow for a new feature? What are the potential benefits and risks?" (Demonstrate understanding of AI's role, responsible AI, and process optimization.)

• "Imagine a scenario where an AI-generated UI component doesn't meet our design system or accessibility standards. How would you address this, and what steps would you take to ensure compliance?" (Showcase your attention to detail, design system knowledge, and problem-solving skills.) Company & Culture Questions:

• "What interests you about Caseware and our mission to serve accounting and audit professionals?" (Research Caseware's impact, values, and industry position.)

• "Our design team is actively evolving its use of AI. How do you see yourself contributing to this evolution and shaping the team's practices?" (Align your experience with their innovative approach.)

• "Describe a time you had to influence stakeholders or drive a cross-team initiative without formal authority. How did you build consensus?" (Highlight your collaboration and communication skills.) Portfolio Presentation Strategy:

• Structure for Impact: Organize your presentation logically, starting with the problem, your role, your process (emphasizing AI use), your solutions, and the measurable outcomes.

• Quantify Results: Whenever possible, use metrics to demonstrate the impact of your designs (e.g., increased user satisfaction, improved task completion rates, reduced errors).

• Highlight AI Contributions: Make it clear where and how AI tools were used, the rationale behind their use, and how you refined the output.

• Showcase Leadership: For each project, articulate your specific contributions, any leadership roles you took, and how you guided the design process or mentored others.

• Be Prepared for Deep Dives: Anticipate questions about your design decisions, trade-offs made, and alternative approaches considered. Practice articulating your reasoning clearly.

📝 Enhancement Note: The interview preparation questions are tailored to probe the candidate's experience with AI in design, their leadership capabilities, and their understanding of the specific industry and company context.

📌 Application Steps

To apply for this Senior UX Designer position:

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

• Curate Your Portfolio: Select 2-3 key projects that best demonstrate your end-to-end UX design process, leadership in ambiguous situations, and, critically, your experience with AI-assisted design tools (Figma Make, Claude Code, Replit). Ensure case studies clearly outline the problem, your role, your process (including AI integration), the solutions, and the outcomes.

• Optimize Your Resume: Tailor your resume to highlight your 3+ years of UX experience, specific achievements in design leadership, user research, design systems, and any experience with AI tools or the financial services industry. Use keywords from the job description.

• Prepare Your Presentation: Practice walking through your portfolio projects, focusing on articulating your design thinking, decision-making rationale, and the impact of your work. Be ready to discuss your approach to responsible AI and human oversight.

• Research Caseware: Understand Caseware's products, their market position in the Fintech/accounting software space, and their company values, particularly "Many Voices, One Team" and their commitment to innovation.

⚠️ 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.