UX Designer

📍 Job Overview

Job Title: UX Designer

Company: OLIVER Agency - North America

Location: Toronto, ON

Job Type: Full-Time

Category: UX/UI Design

Date Posted: 2026-05-01T18:14:51

Experience Level: Mid-Senior (5-10 years inferred)

Remote Status: On-site

🚀 Role Summary

• Design and develop user-centered digital experiences that enhance user engagement and task completion across various touchpoints.

• Conduct comprehensive user research, including interviews, usability testing, and journey mapping, to inform and validate design decisions.

• Create detailed wireframes, user flows, and interactive prototypes to effectively communicate design intent and gain stakeholder alignment.

• Collaborate closely with product managers, developers, and content strategists to ensure seamless execution of designs within agile development cycles.

• Leverage Generative AI tools to augment the design process, from research synthesis and ideation to content creation and iteration.

📝 Enhancement Note: The role explicitly mentions managing Sitecore CMS and Jira, indicating a need for operational efficiency in content management and project tracking, which is crucial for GTM-focused operations. The emphasis on "measurable results" and "key business metrics" suggests a strong alignment with revenue operations principles.

📈 Primary Responsibilities

• Design user experiences that actively reduce friction and improve task completion rates across all digital touchpoints for clients.

• Develop comprehensive wireframes, prototypes, and user flows that clearly articulate design intent and facilitate stakeholder understanding.

• Execute user research activities, including in-depth interviews, usability testing sessions, and detailed journey mapping, to gather actionable insights.

• Foster strong collaboration with product managers, development teams, and content strategists to ensure the successful and cohesive implementation of designed experiences.

• Build, maintain, and evolve robust design systems that guarantee consistency and scalability across multiple platforms and products.

• Translate complex user insights and business requirements into testable design hypotheses, driving iterative improvements.

• Champion and implement accessibility standards (WCAG) and inclusive design practices across all digital products.

• Present design rationale and outcomes clearly to clients and stakeholders, effectively linking design decisions to tangible business results and ROI.

• Continuously research and integrate emerging UX trends, platform guidelines, and new technologies to elevate user experiences.

• Deliver designs specifically aimed at improving key performance indicators such as conversion rates, user satisfaction scores, and task completion efficiency.

• Manage and maintain the Sitecore CMS platform, including the development of content templates, components, and workflows to optimize performance and user experience.

• Effectively manage project tickets and workflows within the Jira ticketing system, ensuring efficient project progression.

• Troubleshoot technical issues related to digital platforms and provide timely and effective resolutions.

📝 Enhancement Note: The responsibilities clearly indicate a hands-on role involving both strategic design and operational execution, particularly with Sitecore CMS and Jira. This blend is common in GTM operations roles where designers need to understand and influence the operational backend driving user-facing platforms.

🎓 Skills & Qualifications

Education: Bachelor's degree in Design, Human-Computer Interaction, Psychology, or a related field, or equivalent practical experience.

Experience: 5-10 years of experience in UX Design, with a strong emphasis on user-centered design processes and systems thinking.

Required Skills:

• A comprehensive portfolio demonstrating a user-centered design process, strong problem-solving capabilities, and effective systems thinking.

• Proficiency in industry-standard design tools such as Figma, Sketch, or Adobe XD, alongside prototyping tools like InVision or Principle.

• Proven experience with user research methodologies, including usability testing, user interviews, and analytics interpretation to drive design strategy.

• Solid understanding of responsive design principles and accessibility standards (WCAG) to ensure inclusive and equitable user experiences.

• Ability to create clear, effective wireframes, user flows, and interactive prototypes that guide development teams accurately.

• Exceptional communication and presentation skills, essential for articulating design rationale and facilitating collaborative workshops with diverse stakeholders.

• Experience working within agile development environments and collaborating effectively with cross-functional teams.

• Foundational understanding of HTML, CSS, and JavaScript fundamentals to inform design constraints and possibilities.

• Proficiency with Generative AI tools (e.g., ChatGPT, Claude, Figma AI, Miro AI) to enhance research synthesis, content creation, and ideation processes.

Preferred Skills:

• Experience utilizing AI tools for user research analysis, persona development, and design iteration cycles.

• A deep understanding of AI capabilities and limitations within UX design, maintaining a strong human-centered evaluation approach.

• Demonstrated ability to leverage AI tools effectively while maintaining a steadfast focus on real user needs and established usability principles.

• Prior experience designing for complex environments such as financial services, fintech, or other regulated industries.

• Knowledge of data visualization techniques and dashboard design principles.

• Experience with user testing platforms like Maze, UsabilityHub, or UserTesting to gather rapid feedback.

• Understanding of conversion optimization strategies and A/B testing methodologies to drive measurable business impact.

• Motion design skills for creating engaging micro-interactions and transitions.

📝 Enhancement Note: The emphasis on "agentic mindset," AI proficiency, and experience in regulated industries suggests a need for a proactive, technically adept designer who can navigate complex business requirements and leverage emerging technologies for GTM efficiency.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase a robust user-centered design process, clearly illustrating problem definition, research, ideation, prototyping, and testing phases.

• Include case studies that highlight systems thinking, demonstrating how designs integrate into larger ecosystems and workflows.

• Present examples of wireframes, user flows, and interactive prototypes that effectively communicate complex user journeys and interactions.

Process Documentation:

• Detail how user research findings are synthesized and translated into actionable design requirements and iterative improvements.

• Illustrate the process of building and maintaining design systems for consistency and scalability across multiple projects.

• Explain methodologies for collaborating with development and product teams, including how design handoffs are managed.

• Provide examples of how accessibility and inclusive design principles are integrated into the design workflow.

📝 Enhancement Note: The portfolio requirements are critical for this role, emphasizing not just the final designs but the process behind them. This aligns with operations roles that value documented workflows, systematic approaches, and measurable improvements.

💵 Compensation & Benefits

Salary Range: $93,500.00 CAD - $104,500.00 CAD per year.

Benefits:

• Comprehensive health, dental, and vision insurance plans.

• Generous paid time off (PTO) and holiday schedule.

• Opportunities for professional development, training, and conference attendance.

• Contribution to a retirement savings plan (e.g., RRSP matching).

• Employee assistance program (EAP) for well-being support.

• Potential for performance-based bonuses.

Working Hours: Standard 40-hour work week, with potential for flexibility depending on project needs and team collaboration requirements.

📝 Enhancement Note: The salary range provided is specific to Toronto, Canada, and is a key piece of information for candidates. The mention of "key performance indicators" and "business outcomes" in the job description suggests that benefits could also be tied to performance, a common practice in operations-focused roles.

🎯 Team & Company Context

🏢 Company Culture

Industry: Marketing & Advertising, Technology, AI Solutions. OLIVER Agency specializes in building bespoke in-house agencies for clients, leveraging AI to drive creativity and efficiency. This positions them at the intersection of traditional marketing services and cutting-edge technology.

Company Size: Part of The Brandtech Group, which partners with over 300 clients in 40+ countries. This suggests a large, global organization with a significant operational footprint.

Founded: 2004. With a long history, OLIVER has established itself as a leader in its niche, adapting to market changes and technological advancements.

Team Structure:

• The UX team likely operates within client-specific "in-house agencies" or project teams, fostering close collaboration with client stakeholders and internal OLIVER teams.

• Reporting likely involves a design lead or manager, with direct collaboration across product, development, content, and client management functions.

Methodology:

• Data analysis and insights are central to informing design decisions, with a focus on measurable results and business outcomes.

• Workflow planning and optimization are critical, especially given the agency's model of building and running in-house marketing ecosystems.

• Automation and efficiency practices are enhanced by the company's investment in AI technologies, aiming to streamline creative and marketing processes.

Company Website: https://oliver.agency/

📝 Enhancement Note: OLIVER's unique model of in-house agencies means the UX Designer will likely work very closely with client business objectives, mirroring the GTM focus on driving revenue and client success through operational excellence. The integration of AI is a significant differentiator.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned as a Mid-Senior UX Designer, responsible for translating complex user needs into elegant, measurable solutions. It requires a blend of strategic thinking, hands-on execution, and operational awareness (CMS, Jira).

Reporting Structure: The designer will report to a Design Lead or Manager, with frequent interaction and collaboration with Product Managers, Developers, Content Teams, and potentially Client Leads.

Operations Impact: The UX Designer's impact is directly tied to improving key business metrics such as conversion rates, user satisfaction, and task completion. This role is crucial for optimizing the digital touchpoints that drive client success and, by extension, OLIVER's revenue growth.

Growth Opportunities:

• Specialization: Deepen expertise in AI-augmented UX design, specific industry verticals (e.g., financial services), or advanced UX research methodologies.

• Leadership: Progress to a Senior UX Designer role, leading projects, mentoring junior designers, or taking on UX lead responsibilities for key accounts.

• Cross-functional: Develop a stronger understanding of the broader GTM operations, including CMS management, project management, and client strategy, potentially leading to hybrid roles.

📝 Enhancement Note: The growth opportunities highlight a path towards more strategic and potentially leadership roles within the operations and design functions, emphasizing the value of operational execution and business impact.

🌐 Work Environment

Office Type: On-site in Toronto, ON. This suggests a collaborative office setting conducive to team interaction and client engagement.

Office Location(s): Toronto, ON, Canada.

Workspace Context:

• The environment is likely dynamic, fast-paced, and client-focused, requiring adaptability and strong collaboration skills.

• Access to modern design and project management tools, including AI-powered platforms, is expected.

• Frequent interaction with diverse teams (design, development, product, content) will be a daily occurrence, fostering a rich learning environment.

Work Schedule: A standard 40-hour work week is expected, with the understanding that project demands may occasionally require flexibility. This allows for structured work while accommodating the need for deep focus on complex design and operational tasks.

📝 Enhancement Note: The on-site requirement implies a strong emphasis on team collaboration and direct client interaction, which is often a hallmark of successful GTM operations teams that rely on close-knit communication.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A recruiter or hiring manager will review your application and portfolio for alignment with core requirements.

• Portfolio Review & Technical Interview: Expect a deep dive into your portfolio, focusing on your design process, problem-solving skills, and ability to articulate rationale. This may include discussing case studies and specific projects.

• Skills Assessment: A practical exercise or technical challenge may be given, potentially involving a design problem, a critique, or a simulated workflow task (e.g., using Jira, proposing Sitecore CMS improvements).

• Team/Stakeholder Interviews: Meet with potential team members and stakeholders to assess cultural fit, collaboration style, and ability to integrate into the agency's client-focused model.

• Final Interview: A discussion with senior leadership to finalize the decision, focusing on your strategic thinking and potential impact.

Portfolio Review Tips:

• Showcase Process: Clearly articulate your thought process, research methods, and iteration cycles for each project. Don't just show final screens.

• Quantify Impact: Where possible, demonstrate the business impact of your designs using metrics (e.g., "increased conversion by X%", "reduced task completion time by Y%").

• Highlight AI Integration: Showcase how you've used AI tools to enhance your UX process, research, or ideation.

• Tailor to the Role: Emphasize projects that demonstrate experience with CMS platforms, regulated industries, or complex systems if applicable.

• Accessibility & Inclusivity: Clearly present how you've incorporated WCAG standards and inclusive design principles.

Challenge Preparation:

• Practice articulating your design decisions concisely and persuasively, linking them to user needs and business objectives.

• Be prepared to discuss your experience with Sitecore CMS, Jira, and AI tools in a practical context.

• Familiarize yourself with OLIVER's approach to in-house agencies and its use of AI.

• Review common UX challenges related to conversion optimization, user engagement, and complex workflows.

📝 Enhancement Note: The interview process emphasizes demonstrating not just design skill but also operational understanding and the ability to deliver tangible business results, aligning with the goals of revenue and sales operations.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma, Sketch, Adobe XD, InVision, Principle. Proficiency in at least one of these is essential.

• CMS Management: Sitecore CMS (specific requirement for template, component, and workflow development).

• Project Management: Jira (for managing project tickets and workflows).

Analytics & Reporting:

• Familiarity with user analytics platforms (e.g., Google Analytics, Adobe Analytics) for interpreting data and informing design.

• Experience with A/B testing and conversion optimization tools.

CRM & Automation:

• While not explicitly mentioned, an understanding of how UX design impacts CRM data and automation workflows would be beneficial.

📝 Enhancement Note: The explicit mention of Sitecore CMS and Jira highlights the operational aspects of this UX role. Candidates with experience in these tools will have a significant advantage, as they demonstrate an understanding of managing digital assets and project lifecycles, crucial for GTM operations.

👥 Team Culture & Values

Operations Values:

• Ambitious: Driving for success and continuous improvement in design and operational outcomes.

• Imaginative: Pushing creative and technological boundaries, particularly with AI integration.

• Inspirational: Producing groundbreaking work that sets new standards.

• Always Learning & Listening: Continuously acquiring new skills and understanding user/stakeholder needs.

• Results-Focused: Prioritizing measurable outcomes and exceeding expectations.

• Actively Pro-Inclusive and Anti-Racist: Fostering a diverse, equitable, and respectful environment.

Collaboration Style:

• Emphasis on cross-functional integration, working closely with product, development, and content teams to achieve shared goals.

• A culture of open feedback and collaborative workshop facilitation to refine designs and processes.

• Proactive knowledge sharing and a willingness to experiment with new approaches, including AI-driven methodologies.

📝 Enhancement Note: The company values, particularly "Results-Focused" and "Ambitious," strongly align with the performance-driven nature of revenue and sales operations. The emphasis on learning and listening also points to a culture that values continuous improvement and feedback loops, essential for operations.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing diverse client needs and business objectives with user-centric design principles in a fast-paced agency environment.

• Effectively integrating Generative AI into the UX workflow while maintaining human oversight and ethical considerations.

• Managing complex digital platforms like Sitecore CMS and ensuring optimal performance and user experience.

• Navigating technical constraints and collaborating with development teams to ensure feasible and high-quality implementations.

Learning & Development Opportunities:

• Deep dive into AI applications for UX research, ideation, and content generation.

• Gain expertise in managing and optimizing enterprise-level CMS platforms like Sitecore.

• Develop advanced skills in user research, usability testing, and A/B testing for conversion optimization.

• Opportunities to lead design initiatives, mentor junior team members, and potentially move into more strategic or managerial roles.

• Exposure to a wide range of client industries and business challenges, fostering broad problem-solving capabilities.

📝 Enhancement Note: The challenges and growth opportunities highlight the dynamic nature of this role, requiring adaptability, continuous learning, and a proactive approach to problem-solving, all hallmarks of effective operations professionals.

💡 Interview Preparation

Strategy Questions:

• "Describe a complex user problem you solved using a human-centered design process. How did you measure the success of your solution?" (Focus on process, metrics, and user advocacy).

• "How would you approach designing an experience for a regulated industry like financial services, considering both user needs and compliance requirements?" (Highlight your understanding of constraints and risk mitigation).

Company & Culture Questions:

• "How does OLIVER's model of bespoke in-house agencies differ from traditional agency structures, and how would you thrive in such an environment?" (Research OLIVER's model and articulate your collaborative, client-focused approach).

• "Our values include 'Ambitious' and 'Results-Focused.' Can you provide an example of how you've demonstrated these values in a previous role?" (Prepare specific examples showcasing your drive and impact).

Portfolio Presentation Strategy:

• Structure your presentation around 2-3 key projects that best showcase your process, problem-solving, and impact.

• For each project, clearly define the problem, your role, your process (research, ideation, design, testing), the solutions, and the measurable outcomes.

• Be prepared to discuss your experience with Sitecore CMS, Jira, and AI tools in the context of your projects.

• Highlight how your designs connect to business objectives and key performance indicators.

• Practice presenting your work concisely, allowing time for Q&A.

📝 Enhancement Note: The interview questions are designed to assess not only design skills but also an understanding of business impact, operational awareness, and adaptability to new technologies like AI, which are critical for operations roles.

📌 Application Steps

To apply for this UX Designer position:

• Submit your application through the provided link on Greenhouse.

• Tailor your resume: Highlight experience with user research, prototyping tools (Figma, Sketch), accessibility (WCAG), CMS platforms (Sitecore), project management tools (Jira), and Generative AI. Use keywords from the job description.

• Curate your portfolio: Select projects that best demonstrate your user-centered design process, problem-solving skills, systems thinking, and ability to deliver measurable results. Ensure it includes examples of wireframes, user flows, prototypes, and case studies with quantifiable outcomes.

• Prepare for interview questions: Practice articulating your design process, rationale, and experience with specific tools and methodologies. Be ready to discuss how your work drives business metrics.

• Research OLIVER Agency: Understand their unique in-house agency model, their AI integration strategy, and their company values to demonstrate genuine 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.

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