Director, UX UI

📍 Job Overview

Job Title: Director, UX/UI

Company: CARET

Location: Toronto, Ontario, Canada

Job Type: Full-time

Category: Design Operations / Product Design Leadership

Date Posted: May 04, 2026

Experience Level: 8+ Years (with previous leadership)

Remote Status: On-site

🚀 Role Summary

• Lead the strategic evolution and hands-on execution of UX/UI design within a B2B SaaS environment, transforming a nascent function into a high-impact, user-centered capability.

• Define and implement a comprehensive design vision, roadmap, and operating system that integrates user research, design principles, and a scalable design system across the product portfolio.

• Champion a culture of design excellence, fostering strong partnerships with Product, Engineering, Customer Success, and Go-to-Market teams to ensure user-centricity is embedded in product strategy.

• Drive the adoption of modern design processes, tools, and methodologies, including the thoughtful integration of AI into user experiences to enhance automation and decision support.

📝 Enhancement Note: This role is positioned as a critical leadership opportunity to build and scale a design function from the ground up within a growing B2B SaaS company. The emphasis on "player-coach" indicates a need for both strategic vision and hands-on execution, typical for a Director-level role in a company that is maturing its design maturity. The focus on AI integration suggests a forward-thinking approach to product development.

📈 Primary Responsibilities

• Define and articulate the long-term design vision and translate it into an actionable strategy and roadmap with measurable incremental progress.

• Establish and nurture a collaborative design culture, positioning UX/UI as a strategic partner across Product, Engineering, CS, and GTM functions.

• Own the end-to-end user experience strategy for the entire product portfolio, ensuring coherence, clarity, and usability across complex workflows.

• Lead hands-on design execution, including the creation of UX flows, wireframes, prototypes, and high-fidelity UI for key product initiatives.

• Develop and mature the company's design system and reusable component library to ensure consistency and scalability.

• Implement efficient design rituals and workflows that balance speed with high-quality outcomes.

• Drive user research initiatives, identifying key priorities, synthesizing insights, and translating them into actionable product recommendations.

• Establish lightweight measurement frameworks to track and report on UX improvements and their impact.

• Champion accessibility standards and advocate for simplicity and consistency in all design outputs.

• Own and optimize design tools (e.g., Figma, Pendo) and leverage behavioral data to inform design decisions and enhance usability.

• Identify opportunities for AI integration within product workflows, automation, and decision support, designing intuitive and trustworthy AI-enabled experiences.

• Manage, mentor, and develop a team of designers, fostering a creative, high-performance culture and shaping future team structure.

📝 Enhancement Note: The responsibilities highlight a dual focus on strategic leadership and tactical execution. The emphasis on "player-coach" implies direct contribution to design artifacts while also guiding a team. The inclusion of "AI UX Patterns" and "behavioral data" indicates a modern approach to design and product development.

🎓 Skills & Qualifications

Education: Specific degree requirements are not explicitly stated, but a Bachelor's or Master's degree in Design, Human-Computer Interaction, or a related field is typically expected for this level.

Experience:

• 8+ years of experience in UX/UI or Product Design, with a strong emphasis on B2B SaaS products.

• Proven track record of leadership experience, including managing and developing design teams.

• Experience in building and scaling a design function within a growing organization.

Required Skills:

• Strategic Design Leadership: Ability to define design vision, strategy, and roadmaps for a product portfolio.

• Hands-On Design Execution: Proficiency in UX flows, wireframing, prototyping, and high-fidelity UI design.

• Design Systems: Strong experience in building, maintaining, and scaling design systems and component libraries.

• User Research & Insights: Expertise in conducting user research, usability testing, and synthesizing insights into actionable recommendations.

• Modern Design Tools: Hands-on proficiency with industry-standard design tools, with a specific requirement for Figma.

• B2B SaaS Expertise: Deep understanding of the nuances of designing for business-to-business software applications.

• AI UX Patterns: Familiarity with emerging AI UX patterns and experience designing AI-enhanced features.

• Cross-functional Collaboration: Proven ability to influence and collaborate effectively with Product, Engineering, CS, and GTM teams.

• Systems Thinking: Ability to understand and design for complex, interconnected systems and workflows.

• Data-Driven Design: Experience leveraging behavioral data and analytics to inform design decisions.

• Team Management & Mentorship: Experience managing, coaching, and developing design talent.

Preferred Skills:

• Experience with Pendo for product analytics and user engagement.

• Familiarity with legal or accounting technology sectors.

• Understanding of accessibility standards and implementation.

• Experience with A/B testing and conversion optimization for user interfaces.

📝 Enhancement Note: The requirement for "8+ years in UX/UI or Product Design (B2B SaaS required) with previous leadership experience" clearly defines the seniority. The "player-coach" aspect is crucial, indicating that candidates must be comfortable with both strategic planning and hands-on design work. The specific mention of Figma is a critical technical requirement.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Demonstrate a strong track record of leading design initiatives from concept to launch within B2B SaaS environments.

• Showcase complex workflow design examples, illustrating problem-solving skills and user-centered solutions.

• Present evidence of building or significantly contributing to design systems and their impact on product consistency and efficiency.

• Include case studies that highlight user research methodologies, the insights derived, and how they informed design decisions.

• Feature examples of UI craft, demonstrating attention to detail, visual hierarchy, and user interface best practices.

• Illustrate experience with prototyping tools and the ability to convey interaction design effectively.

Process Documentation:

• Provide examples of how you've introduced or refined design processes (e.g., design sprints, user testing rituals, design critique sessions) in previous roles.

• Document instances where you've established workflows that balance development velocity with design quality and user experience.

• Showcase how you've leveraged data (user research, analytics, A/B testing) to drive design iteration and measure impact.

• Illustrate experience in defining and implementing design system governance and contribution processes.

📝 Enhancement Note: A strong portfolio is paramount for this role, as it's explicitly mentioned as a requirement. The emphasis should be on demonstrating strategic impact, hands-on capability, and leadership in scaling a design function, particularly within a B2B SaaS context. The portfolio needs to show how the candidate has moved beyond individual contribution to strategic influence and team development.

💵 Compensation & Benefits

Salary Range: $150,000 - $160,000 CAD per year.

Benefits:

• Flexible Paid Time Off (PTO)

• Comprehensive Medical, Dental, Vision, and Supplemental Coverage

• Paid Sick Days

• Flexible Spending Account (FSA)

• Health Savings Account (HSA)

• 401(k) with company match

Working Hours: Standard full-time hours (likely 40 hours per week), with an on-site work arrangement. Flexibility may be offered within the standard work week, but the role is based in Toronto.

📝 Enhancement Note: The provided salary range is specific to CAD and for Toronto. The listed benefits are standard for a full-time leadership role in North America, with a notable inclusion of both FSA and HSA options, suggesting a comprehensive health benefits package. The "Flexible PTO" is a positive indicator of work-life balance consideration.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology, specifically B2B SaaS focusing on practice management, document automation, and payment processing for legal and accounting firms. This positions CARET within the FinTech and LegalTech sectors.

Company Size: The description mentions CARET empowers over 10,000 firms, suggesting a significant customer base. LinkedIn data indicates a company size of 201-500 employees, placing it in the mid-size company category, which is often characterized by a blend of established processes and room for rapid growth and innovation.

Founded: CARET's founding date is not explicitly stated in the provided text, but its focus on "latest in technology and automation" implies a modern, forward-thinking company.

Team Structure:

• The UX/UI team is described as "nascent," implying it's either very small or in the early stages of formalization. The Director will be responsible for building and shaping this team.

• Reporting structure will likely place the Director of UX/UI under a VP of Product or Chief Product Officer, given the strategic nature of the role.

Methodology:

• Data-Driven Design: Decisions are expected to be grounded in evidence, leveraging behavioral data, user research, and analytics.

• User-Centered Design: A core tenet of the role is to champion user research and insights to inform product strategy and design.

• Agile Development: The role operates within a fast-paced, agile environment, requiring workflows that balance velocity with quality.

• Process Improvement: Introducing design rituals, refining workflows, and expanding the design system are key responsibilities aimed at enhancing efficiency and outcomes.

Company Website: getcaret.com

📝 Enhancement Note: CARET operates in a specialized B2B market (legal and accounting tech), which often requires a deep understanding of user workflows and regulatory environments. The company values "succeed together," "embrace progress," "care big," and "create space," suggesting a collaborative, forward-thinking, and supportive culture.

📈 Career & Growth Analysis

Operations Career Level: Director level, indicating significant leadership responsibility for a functional area. This role is crucial for shaping the company's product experience and establishing best practices in design. It's a "player-coach" position, demanding both strategic oversight and hands-on contribution.

Reporting Structure: The Director will likely report to a senior product leader (e.g., VP of Product, CPO) and will be responsible for managing and developing a team of designers. They will need to collaborate extensively with Engineering and Product Management leads.

Operations Impact: The Director of UX/UI has a direct and substantial impact on revenue and business decisions by:

• Enhancing User Experience: Leading to higher customer satisfaction, retention, and reduced churn.

• Driving Product Adoption: Intuitive and effective design encourages deeper product usage and feature adoption.

• Improving Operational Efficiency: Well-designed products can reduce support costs and streamline user workflows.

• Informing Product Strategy: User insights gathered by the design team directly influence product roadmap prioritization and feature development.

• Shaping Brand Perception: High-quality UX/UI contributes to a strong brand image and competitive differentiation.

Growth Opportunities:

• Team Expansion & Leadership: Opportunity to build and grow the design team from its current nascent stage, defining roles and hiring strategically.

• Strategic Influence: Play a pivotal role in shaping the product vision and strategy, influencing the direction of B2B SaaS solutions for legal and accounting professionals.

• Technological Advancement: Opportunity to lead the integration of cutting-edge technologies like AI into user experiences, staying at the forefront of design innovation.

• Cross-functional Leadership: Develop broader leadership skills by collaborating across multiple departments and contributing to overall business strategy.

• Industry Expertise: Deepen knowledge within the legal and accounting tech sectors, becoming a subject matter expert in user needs and market trends.

📝 Enhancement Note: The "player-coach" designation suggests that while this is a leadership role, the individual will still be expected to contribute directly to design work. This is common in growing companies where the initial leader needs to set the bar and actively participate. Growth opportunities are substantial given the "nascent" state of the design function.

🌐 Work Environment

Office Type: This is an on-site role, indicating a traditional office-based work environment. The address at "1 Yonge St, Suite 2000" in Toronto suggests a modern office space in a prominent downtown location.

Office Location(s): The primary office is located at 1 Yonge St, Suite 2000, Toronto, Ontario, M5E 1E5 1W7, Canada. This downtown Toronto location offers excellent accessibility via public transit and is situated in a major business hub.

Workspace Context:

• Collaborative Environment: The emphasis on cross-functional collaboration suggests a workspace designed to facilitate interaction between design, product, and engineering teams. Open-plan areas or shared project spaces might be common.

• Tools & Technology: Expect access to modern design and collaboration tools, with a specific emphasis on Figma as the primary design tool. The company likely provides necessary hardware and software for design and research activities.

• Team Interaction: Opportunities for direct interaction with designers, product managers, engineers, and other stakeholders are inherent in an on-site role, fostering a strong sense of team and shared purpose.

Work Schedule: The role is full-time, likely adhering to standard business hours in Toronto (e.g., 9:00 AM - 5:00 PM EST). While the company values "create space," suggesting a supportive culture, the on-site requirement means predictable office attendance is expected. Flexibility within the workday might be possible, but core hours will likely be required for team collaboration.

📝 Enhancement Note: The on-site requirement in a prime Toronto location suggests a company that values in-person collaboration and team cohesion. The specific address indicates a professional office setting within a major metropolitan area.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: HR or recruiter call to assess basic qualifications, experience, and cultural fit.

• Hiring Manager Interview: Discussion with the hiring manager (likely a VP of Product or similar) focusing on leadership experience, strategic vision, and hands-on design capabilities.

• Portfolio Review & Presentation: A dedicated session where candidates present their portfolio, showcasing key projects, design process, and impact. This is where the "player-coach" aspect will be heavily evaluated. Expect questions on how you've built/scaled design functions, handled complex workflows, and integrated user research.

• Cross-functional Interviews: Meetings with key stakeholders from Product Management, Engineering, and potentially GTM to assess collaboration style, communication skills, and ability to influence.

• Design Challenge (Potential): A practical exercise or case study may be given to assess problem-solving skills, design thinking, and execution in a simulated scenario. This might involve critiquing an existing experience or proposing a solution for a hypothetical problem.

• Final Interview: Potentially with a senior executive or CEO, focusing on overall strategic alignment, leadership potential, and cultural fit.

Portfolio Review Tips:

• Structure for Impact: Organize your portfolio to clearly articulate the problem, your role, the process, the solution, and the measurable impact/results for each project.

• Showcase Strategy & Execution: Include examples that demonstrate both your strategic thinking (vision, roadmap) and your hands-on design skills (flows, UI, prototypes).

• Highlight B2B SaaS Nuances: Emphasize projects that show understanding of complex user workflows, enterprise needs, and B2B SaaS product challenges.

• Demonstrate Leadership: Include examples of how you've mentored designers, influenced product direction, or scaled design processes.

• Quantify Results: Whenever possible, use metrics (e.g., conversion rates, user satisfaction scores, task completion times, efficiency gains) to demonstrate the impact of your work.

• Figma Proficiency: Be prepared to discuss your workflow in Figma and potentially showcase specific techniques or components you've created.

• AI Integration: If you have experience with AI-enhanced features, clearly articulate the UX challenges and solutions.

Challenge Preparation:

• Understand the Business: Research CARET's products, target market (legal/accounting firms), and competitive landscape.

• Anticipate UX Problems: Think about common UX challenges in professional software, data management, and workflow automation.

• Focus on Process: Be ready to explain your design process step-by-step, emphasizing user research, iteration, and collaboration.

• AI Integration Scenarios: Consider how AI could be thoughtfully applied to improve user efficiency or decision-making within CARET's existing product suite.

• Communication: Practice articulating your design rationale clearly and concisely, as if presenting to both designers and non-designers.

📝 Enhancement Note: The interview process is likely rigorous, given the leadership and "player-coach" nature of the role. The portfolio review is critical, and candidates should prepare to articulate not just the "what" but the "why" and "how" behind their design decisions and leadership actions.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: Explicitly required for hands-on design execution, wireframing, prototyping, and UI design. Proficiency is essential.

• User Research Tools: While not specified, expect tools for conducting interviews, surveys, and usability testing (e.g., UserTesting.com, Maze, Qualtrics, SurveyMonkey).

• Prototyping Tools: Figma's prototyping capabilities will be primary, but familiarity with others (e.g., InVision, Adobe XD) might be beneficial.

• Design System Management: Tools or processes for managing design tokens, components, and documentation.

Analytics & Reporting:

• Pendo: Mentioned as a tool to "own and optimize," suggesting its use for product analytics, user journey mapping, and in-app guidance.

• Web Analytics: Familiarity with tools like Google Analytics or similar for understanding user behavior on product websites or within the application.

• Data Visualization Tools: Experience with tools like Tableau, Power BI, or even advanced Excel for analyzing user data and creating reports.

CRM & Automation:

• CRM System: While not directly a design tool, understanding how design impacts CRM usage (e.g., Salesforce, HubSpot) can be beneficial for B2B SaaS context.

• Project Management Tools: Tools like Jira, Asana, or Trello are commonly used in agile environments for tracking design tasks and project progress.

• Collaboration Tools: Slack, Microsoft Teams for day-to-day communication and team collaboration.

📝 Enhancement Note: The explicit mention of Figma and Pendo indicates the core technology stack for design and product analytics. A strong candidate will have deep expertise in Figma and a working understanding of how to leverage product analytics tools like Pendo to drive design decisions and measure impact.

👥 Team Culture & Values

Operations Values: CARET's stated values are:

• We succeed together: Emphasizes collaboration, teamwork, and shared ownership of outcomes. For a design leader, this means fostering a supportive team environment and building strong cross-functional partnerships.

• We embrace progress: Highlights a commitment to innovation, continuous improvement, and adopting new technologies and methodologies. This aligns with the role's focus on AI integration and evolving the design function.

• We care big: Suggests a focus on empathy—for customers, colleagues, and partners—and a commitment to making a significant positive impact. This translates to user-centric design and a supportive team culture.

• We create space: Implies fostering an environment where individuals can contribute, grow, and have autonomy. For the design team, this means empowering designers and providing them with the resources and freedom to excel.

Collaboration Style:

• Cross-functional Integration: The role demands active collaboration with Product, Engineering, CS, and GTM. This suggests a culture where teams work closely, share insights, and align on objectives.

• Process-Oriented: The emphasis on building a "modern design process & operating system" indicates a culture that values structured approaches to design, iteration, and quality assurance.

• Feedback and Iteration: The expectation to "collaborate closely with Product and Engineering to iterate quickly" points to a culture that embraces feedback loops and iterative development.

• Knowledge Sharing: A leader who fosters a culture of sharing best practices, design learnings, and user insights across teams will thrive.

📝 Enhancement Note: The company values are foundational and should guide how candidates approach their interactions and demonstrate their fit. Emphasizing alignment with "embrace progress" and "succeed together" will be key.

⚡ Challenges & Growth Opportunities

Challenges:

• Building from Nascent: Establishing a mature, strategic design function from an early stage requires significant effort in defining processes, building infrastructure (like a design system), and gaining organizational buy-in.

• Player-Coach Balance: Juggling hands-on design execution with strategic leadership, team management, and stakeholder influence can be demanding.

• Cross-functional Alignment: Ensuring consistent understanding and prioritization of design initiatives across Product, Engineering, and GTM teams can be challenging, especially in a growing company.

• Integrating AI Thoughtfully: Designing effective, trustworthy, and valuable AI-powered user experiences requires navigating new UX paradigms and managing user expectations.

• Scaling the Team: As the company grows, scaling the design team effectively while maintaining quality and culture will be a key challenge.

Learning & Development Opportunities:

• Strategic Design Leadership: Opportunity to shape and grow a critical function, gaining experience in building and leading high-performing design teams.

• Product Strategy Influence: Directly contribute to high-level product decisions and influence the company's technological direction, especially with AI integration.

• Deep Industry Expertise: Develop specialized knowledge in the legal and accounting technology sectors, understanding unique user needs and workflows.

• Advanced UX Methodologies: Explore and implement cutting-edge UX practices, particularly in the emerging field of AI-driven experiences.

• Cross-functional Acumen: Enhance skills in stakeholder management, communication, and strategic partnership across various business units.

📝 Enhancement Note: The challenges are directly linked to the opportunity to build and shape the function. Candidates should frame these challenges as opportunities for impact and growth, demonstrating their problem-solving capabilities.

💡 Interview Preparation

Strategy Questions:

• "How would you approach defining the long-term design vision and roadmap for a nascent UX function in a B2B SaaS company like CARET?" (Focus on your methodology, stakeholder engagement, and phased approach.)

• "Describe your experience building a design system from the ground up or significantly scaling an existing one. What were the key challenges and how did you ensure adoption?" (Highlight your process, collaboration, and metrics for success.)

• "How do you balance hands-on design execution with strategic leadership and team management in a player-coach role?" (Provide specific examples of how you manage your time and priorities.)

• "What are your strategies for integrating user research and behavioral data into the design process to ensure data-driven decision-making?" (Discuss specific techniques you use to gather, synthesize, and apply insights.)

Company & Culture Questions:

• "Based on our company values (succeed together, embrace progress, care big, create space), how would you foster a design culture that embodies these principles?" (Connect your leadership style and team-building approach to the stated values.)

• "How do you build strong, collaborative relationships with Product Management and Engineering teams to ensure design is seen as a strategic partner?" (Discuss your communication strategies and experience working in agile environments.)

Portfolio Presentation Strategy:

• Narrative Arc: Structure each case study with a clear beginning (the problem), middle (your process and solution), and end (the impact and learnings).

• Role Clarity: Explicitly state your role and contributions in each project, especially if it was a team effort.

• Process Visualization: Use diagrams, flowcharts, and visual aids to illustrate your design process, research methods, and iteration cycles.

• Quantify Impact: Back up your claims with data and metrics wherever possible. Show how your design work contributed to business objectives.

• Highlight Leadership: For leadership roles, include examples of how you mentored designers, influenced strategy, or improved team processes.

• Conciseness: Be mindful of time. Focus on the most impactful projects and key learnings. Practice your delivery to ensure it's engaging and efficient.

• Prepare for Questions: Anticipate questions about trade-offs, challenges, alternative solutions, and future iterations.

📝 Enhancement Note: Candidates should prepare to discuss their experience in building and scaling design functions, their approach to a player-coach role, and their perspective on integrating AI into B2B SaaS products. The portfolio presentation is a crucial component for demonstrating both strategic thinking and hands-on craft.

📌 Application Steps

To apply for this Director, UX/UI position at CARET:

• Submit your application through the provided application link on Paycom.

• Portfolio Customization: Tailor your resume and portfolio to highlight your experience in B2B SaaS, leadership, and hands-on UX/UI design. Select 2-3 key projects that best exemplify your ability to build and scale a design function, solve complex workflow problems, and integrate user research.

• Resume Optimization: Ensure your resume clearly outlines your 8+ years of experience, leadership roles, and proficiency with Figma and other relevant design/analytics tools. Quantify achievements and responsibilities where possible.

• Interview Preparation: Thoroughly research CARET's products and target markets. Prepare detailed responses to common interview questions, focusing on strategy, leadership, and your "player-coach" approach. Practice your portfolio presentation, ensuring it's concise, impactful, and addresses the role's requirements.

• Company Research: Understand CARET's mission, values, and the specific challenges faced by legal and accounting firms. This will enable you to articulate how your design leadership can drive value and align with their business objectives.

⚠️ 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.