Senior UX Designer - RMJ

📍 Job Overview

Job Title: Senior UX Designer - RMJ

Company: Redwood Software

Location: Ontario, Canada

Job Type: Full-time

Category: UX/Product Design

Date Posted: March 11, 2026

Experience Level: Mid-Senior Level (5-7 years)

Remote Status: On-site

🚀 Role Summary

• Owns the end-to-end user experience (UX) design for features and complex workflows within the RunMyJobs enterprise automation platform.

• Focuses on designing intuitive interfaces for critical business processes, specifically for finance and IT teams, in areas like job scheduling, workflow orchestration, and monitoring.

• Plays a pivotal role in building a new design system from the ground up, establishing scalable patterns and components across Redwood's product portfolio.

• Conducts user research, including interviews and usability testing, to gather insights and inform design decisions, fostering empathy for enterprise users.

• Collaborates closely with product managers and engineers in an agile environment to deliver high-quality, technically feasible, and user-centered design solutions.

📝 Enhancement Note: While the title is Senior UX Designer, the core responsibilities and required experience suggest a role that bridges product design and specialized UX for complex enterprise systems. The emphasis on building a design system from scratch and collaborating on enterprise-level automation tools indicates a significant impact on the product's foundational user experience and scalability. This role is ideal for a designer who thrives in a B2B SaaS environment and can translate intricate technical processes into user-friendly interfaces.

📈 Primary Responsibilities

• Lead the end-to-end UX design process for entire features and intricate workflows within the RunMyJobs platform.

• Develop user flows, wireframes, interactive prototypes, and high-fidelity visual designs that effectively balance user needs with technical and business constraints.

• Conduct comprehensive user research, including planning and executing interviews, usability tests, and observation sessions, to deeply understand enterprise user behaviors and pain points.

• Synthesize research findings into actionable insights and design recommendations that directly influence product strategy and feature development.

• Collaborate daily with product managers to define feature scope, success metrics, and user stories, ensuring alignment with business objectives.

• Partner closely with engineering teams throughout the agile development lifecycle, participating in ceremonies and ensuring design fidelity through design QA.

• Contribute significantly to the development and evolution of Redwood's new design system, creating reusable components, patterns, and interaction guidelines.

• Document and advocate for design consistency, accessibility standards (e.g., WCAG), and best practices across the entire product portfolio.

• Leverage AI tools daily to accelerate design exploration, content generation, and enhance overall workflow efficiency.

• Mentor junior designers, sharing expertise in UX principles, design systems, and best practices for enterprise software.

📝 Enhancement Note: The responsibilities highlight a blend of individual contribution and strategic leadership. The emphasis on "owning end-to-end UX design" and "building a new design system from the ground up" indicates a senior-level impact. The explicit mention of using AI tools daily suggests a forward-thinking approach to design processes and a requirement for candidates to be adept with emerging technologies in the design space.

🎓 Skills & Qualifications

Education:

Experience:

• 5-7 years of dedicated UX/product design experience, with a strong preference for candidates with a background in B2B SaaS or complex enterprise software environments.

Required Skills:

• Portfolio: A strong and comprehensive portfolio showcasing a full spectrum of UX capabilities, including user research, interaction design, visual design, and prototyping expertise.

• Enterprise UX: Deep experience designing for complex, data-dense enterprise applications, understanding the unique challenges and requirements of B2B users.

• Design Tools: Proficiency with Figma as the primary design tool, alongside experience with other modern design and prototyping software.

• AI Integration: Daily hands-on experience utilizing AI tools (e.g., ChatGPT, Claude, Copilot, Midjourney, or similar) to enhance design productivity, explore concepts, and streamline workflows.

• Agile Methodologies: Proven ability to work effectively within agile development environments, collaborating closely with product managers and engineers.

• Design Principles: Solid understanding of interaction design patterns, information architecture, visual design principles, and user-centered design methodologies.

• User Research: Proven ability to conduct user research activities and translate research findings into actionable design solutions and strategic recommendations.

• Design Systems: Experience in contributing to or actively building design systems, including the creation of reusable components, patterns, and style guides.

• Communication: Excellent verbal and written communication, presentation, and stakeholder management skills, with the ability to articulate design rationale clearly.

Preferred Skills:

• Automation/Workflow Tools: Prior experience designing specifically for automation, workflow management, or developer tools.

• Domain Expertise: Familiarity with enterprise software domains such as ERP, finance, IT operations, or DevOps.

• Accessibility: Knowledge of accessibility standards (e.g., WCAG) and a commitment to inclusive design practices.

• Front-End Collaboration: Understanding of front-end technologies (HTML, CSS, React) to facilitate more effective collaboration with engineering teams.

• AI for Design Systems: Experience using AI tools specifically for design system tasks, such as component generation or design token automation.

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

• Published Work: Contributions to open-source design systems or published design work that demonstrates expertise and thought leadership.

📝 Enhancement Note: The requirement for daily AI tool usage is a significant differentiator, indicating Redwood Software's commitment to leveraging cutting-edge technology in their design process. Candidates should be prepared to discuss specific examples of how they've used AI to improve their design workflow, problem-solving, or creative output. The preference for experience in automation or developer tools suggests that candidates with a technical or systems-oriented mindset will be highly valued.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• End-to-End Case Studies: Showcase at least 2-3 detailed case studies demonstrating your full-stack UX design process. Each case study should cover problem definition, user research methodologies, ideation, wireframing, prototyping, visual design, user testing, and final implementation outcomes.

• Enterprise Complexity: Highlight projects that involved designing for complex, data-dense enterprise applications, illustrating your ability to manage intricate information architecture and user flows.

• Design System Contribution: Include examples of your work on design systems, whether it's contributing to an existing system or building components and patterns from scratch. Showcase your understanding of scalability, reusability, and consistency.

• Problem-Solving Focus: Clearly articulate the business problems and user needs addressed by your design solutions, emphasizing the impact and ROI achieved through your work. Quantifiable results are highly encouraged.

Process Documentation:

• Research Synthesis: Demonstrate how you synthesize user research findings into clear, actionable insights and design recommendations that drive product decisions.

• Workflow Design: Illustrate your process for mapping out and designing complex workflows, showing how you simplify intricate processes for end-users.

• System Integration Awareness: While not requiring direct system implementation, your portfolio should hint at awareness of technical constraints and how your designs integrate with or interact with broader enterprise systems.

• AI Tool Integration: Be prepared to discuss and potentially showcase how you've integrated AI tools into your design process to improve efficiency, explore broader solution spaces, or generate assets.

📝 Enhancement Note: Given the emphasis on building a design system and working with complex enterprise software, portfolio pieces that demonstrate a structured approach to design, scalability, and a deep understanding of user needs in a B2B context will be paramount. Candidates should be ready to walk through their process and explain the rationale behind their design decisions, particularly how they balance user needs with technical feasibility and business objectives.

💵 Compensation & Benefits

Salary Range:

Benefits:

• Comprehensive health and dental insurance plans.

• Generous paid time off (PTO), including vacation days, sick days, and public holidays.

• Retirement savings plan options, such as a Group RRSP or similar.

• Opportunities for professional development, including training, conferences, and certifications.

• Potential for performance-based bonuses or stock options, reflecting the company's growth and employee contributions.

Working Hours:

• Standard full-time working hours are typically 40 hours per week.

• While the role is on-site, Redwood Software may offer some flexibility regarding daily start and end times, as long as core business hours and agile sprint needs are met.

📝 Enhancement Note: The salary range is an estimate based on industry benchmarks for similar roles in Ontario, Canada. Actual compensation may vary based on the candidate's specific experience, skills, and the company's compensation philosophy. The benefits listed are standard for full-time roles in the Canadian tech sector and are assumed based on typical offerings for a company of Redwood Software's profile.

🎯 Team & Company Context

🏢 Company Culture

Industry: Software (specifically, Automation Fabric Solutions for ERP)

Company Size: The provided data indicates Redwood Software is a well-established company, likely in the medium to large enterprise category. Given their global presence and focus on mission-critical business processes, they operate in a highly competitive and specialized segment of the enterprise software market.

Founded: The company was founded with a vision to lead in full-stack automation for mission-critical business processes, emphasizing innovation and SaaS-based solutions. The exact founding year is not provided but implies a history and established market presence.

Team Structure:

• Design Team: The UX Designer will likely be part of a growing design team, contributing to building its foundational elements. This team will include other designers and potentially design operations roles.

• Product & Engineering: Close daily collaboration with Product Managers and Engineers within agile teams is expected. This structure fosters rapid iteration and cross-functional problem-solving.

• Cross-functional Collaboration: The role requires significant interaction with Product Management, Engineering, Customer Success, and potentially Marketing and Sales teams to gather insights and ensure product-market fit.

Methodology:

• Agile Development: The team operates within agile ceremonies, maintaining design velocity alongside engineering sprints. This implies iterative development, regular stand-ups, sprint planning, and retrospectives.

• User-Centered Design: A strong emphasis is placed on user research and incorporating user feedback into the design process to ensure intuitive and effective solutions.

• Data-Driven Decisions: While not explicitly detailed, the expectation to define success metrics and partner with customer success suggests a data-informed approach to product development and design validation.

Company Website: Redwood.com

📝 Enhancement Note: Redwood Software positions itself as a leader in a critical niche of enterprise automation. The company culture appears to be driven by innovation, customer success, and a collaborative, results-oriented approach, as evidenced by their core values. The emphasis on "lights-out automation" suggests a focus on efficiency, reliability, and advanced technological solutions.

📈 Career & Growth Analysis

Operations Career Level: This role is a Senior UX Designer position, indicating a mid-to-senior career stage. It requires significant independent contribution, ownership of complex features, and the ability to mentor others. It sits above a standard UX Designer but below a Lead or Principal Designer, focusing on execution and system building.

Reporting Structure: The Senior UX Designer will likely report to a Design Lead, Head of Design, or a Product Design Manager. They will work within cross-functional product teams, collaborating closely with Product Managers and Engineering Leads.

Operations Impact: The role has a direct impact on the usability and effectiveness of Redwood's core enterprise automation platform, RunMyJobs. By creating intuitive and efficient user experiences, the Senior UX Designer will enable finance and IT professionals to better manage critical business processes, leading to increased customer satisfaction, reduced support costs, and enhanced operational efficiency for Redwood's clients. Their work in building the design system will also ensure scalability and consistency across the entire product portfolio, impacting future product development and brand perception.

Growth Opportunities:

• Design Leadership: Potential to grow into a Lead UX Designer or Design Manager role, overseeing a team or a specific product area, especially as the design system matures.

• Specialization: Deepen expertise in enterprise UX, automation tools, or design systems, becoming a go-to subject matter expert within the company.

• Product Strategy: Contribute more significantly to product strategy through advanced user research and insights, influencing the product roadmap.

• Mentorship: Continue to mentor junior designers, fostering a strong design culture within the organization.

• AI in Design: Become an internal champion for leveraging AI in design, developing new methodologies and best practices.

📝 Enhancement Note: The emphasis on building a design system from scratch and the requirement for AI tool proficiency suggest that growth opportunities will be tied to the candidate's ability to innovate and establish best practices within these areas. Success in this role could lead to significant influence on the future direction of Redwood's product design.

🌐 Work Environment

Office Type: The role is explicitly stated as "On-site," indicating a traditional office environment rather than remote or hybrid. This suggests a workplace designed for in-person collaboration and team synergy.

Office Location(s): The job is located in Ontario, Canada. This likely means the role is based in one of Redwood Software's established offices within the province, potentially in a major city or tech hub like Toronto, Ottawa, or Waterloo, which are known for their technology sectors.

Workspace Context:

• Collaborative Spaces: Expect an office environment that encourages collaboration, likely featuring meeting rooms, breakout areas, and open-plan workspaces alongside dedicated desks.

• Technology Access: As a software company, the office will be equipped with modern technology, including reliable internet, high-performance workstations, and access to necessary design and development software.

• Team Interaction: The on-site nature facilitates regular face-to-face interaction with colleagues, fostering a strong sense of team cohesion and enabling spontaneous problem-solving sessions.

Work Schedule:

• The standard work schedule is likely Monday to Friday, aligning with typical business hours. Given the agile environment, there may be a need for flexibility to attend team meetings or address urgent project needs, but the core expectation is a structured on-site presence.

📝 Enhancement Note: The on-site requirement is a key factor for candidates. It suggests a company that values in-person collaboration, team dynamics, and a structured work environment. Candidates should consider the commute and their preference for a physical workspace when evaluating this opportunity.

📄 Application & Portfolio Review Process

Interview Process:

1. Initial Screening: A brief call with a recruiter or HR representative to assess basic qualifications, interest in the role and company, and alignment with company culture.

2. Hiring Manager Interview: A deeper dive with the hiring manager (likely a Design Lead or Product Manager) to discuss experience, motivations, and understanding of UX principles, enterprise design, and the specific responsibilities of the role.

3. Portfolio Review & Design Challenge: This is a critical stage. Candidates will present their portfolio, walking through key case studies. They may also be given a design challenge to complete either before or during this interview, focusing on problem-solving for a complex enterprise scenario, design system thinking, or workflow simplification.

4. Team Interviews: Interviews with potential peers (other designers, engineers, product managers) to assess collaboration style, communication skills, and cultural fit.

5. Final Round: Potentially a final interview with a senior leader (e.g., Head of Product, VP of Engineering) to discuss strategic thinking, leadership potential, and overall fit with Redwood's mission.

Portfolio Review Tips:

• Storytelling: Structure your portfolio around compelling narratives. For each case study, clearly define the problem, your role, the process you followed, the challenges you overcame, and the impactful results achieved.

• Process Over Polish: While visual design is important, emphasize your thought process, research methodologies, and how you arrived at your solutions. Demonstrate your ability to tackle ambiguity and complex problems.

• Enterprise Focus: Highlight projects that demonstrate your understanding of B2B SaaS and enterprise software design. Showcase your ability to handle data-dense interfaces, complex workflows, and the needs of professional users (finance, IT).

• Design System Examples: Clearly present your contributions to design systems, illustrating your grasp of component-based design, scalability, and consistency.

• AI Integration: Be prepared to articulate how you've used AI tools in your design workflow. Have specific examples ready, such as using AI for ideation, content generation, or workflow optimization, and be ready to discuss the benefits.

• Conciseness: Focus on your most relevant and impactful work. Tailor your presentation to the specific requirements of this Senior UX Designer role at Redwood Software.

Challenge Preparation:

• Understand the Domain: Familiarize yourself with enterprise automation, ERP systems, job scheduling, and workflow orchestration concepts. Redwood's website and the job description are good starting points.

• Design System Thinking: Practice designing components or patterns that could fit into a scalable design system. Consider how to ensure accessibility and consistency.

• Problem-Solving: Be ready to break down a complex problem into smaller, manageable parts, identify user needs, and propose user-centered solutions.

• AI Application: Consider how AI tools could be leveraged to solve hypothetical design challenges presented in a case study.

📝 Enhancement Note: The emphasis on AI tools and design systems suggests that candidates who can demonstrate practical application and strategic thinking in these areas will stand out. Be ready to discuss not just that you used AI, but how and why it improved your process or outcome.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: This is explicitly stated as the primary tool. Proficiency in Figma for wireframing, prototyping, UI design, and collaboration is essential.

• Prototyping Tools: While Figma is primary, familiarity with other prototyping tools is beneficial for a broader understanding of design capabilities.

• Design System Tools: Experience with tools or methodologies for managing design systems, tokens, and component libraries within Figma or other platforms.

Analytics & Reporting:

• User Analytics Platforms: Familiarity with tools like Google Analytics, Mixpanel, Amplitude, or similar, to understand user behavior and measure the impact of design changes.

• Data Visualization Tools: Experience with tools that help visualize user data and performance metrics to inform design decisions.

CRM & Automation:

• Enterprise Automation Platforms: While not a direct tool requirement for the designer, understanding the context of platforms like RunMyJobs, and potentially other ERP/workflow automation systems (e.g., SAP, Oracle, ServiceNow), is crucial for empathy and effective design.

• AI Tools: Daily hands-on experience with AI tools such as ChatGPT, Claude, Copilot, Midjourney, or similar for accelerating design exploration, content generation, workflow efficiency, and potentially design system tasks.

📝 Enhancement Note: The explicit mention of Figma and daily AI tool usage are critical. Candidates should be prepared to discuss their proficiency with Figma in detail, including advanced features for collaboration and design system management. For AI tools, specific examples of their application in the design process are key.

👥 Team Culture & Values

Operations Values:

• One Team. One Redwood: Emphasizes collaboration, unity, and working towards common goals across departments and individuals. For a UX Designer, this means actively contributing to team success and supporting colleagues.

• Make Your Own Weather: Encourages proactivity, initiative, and taking ownership of challenges and opportunities. Designers are expected to be self-starters and drive progress.

• Obsess over Customer Success: Places a high premium on understanding and exceeding customer expectations. Designers must deeply empathize with users and design solutions that deliver significant value and satisfaction.

• Work the Problem: Promotes a focused, analytical approach to problem-solving. Designers should be adept at dissecting complex issues, understanding root causes, and developing effective, data-informed solutions.

• Be Curious: Fosters a spirit of continuous learning, exploration, and questioning. Designers should be open to new ideas, technologies (like AI), and approaches to design.

• Own the Outcome: Reinforces accountability and a commitment to delivering high-quality results. Designers are expected to take responsibility for their work from conception to successful implementation.

• Respect Each Other: Highlights the importance of a positive, inclusive, and supportive work environment. Mutual respect is foundational to effective teamwork and collaboration.

Collaboration Style:

• Cross-functional Integration: The role demands close, daily collaboration with product managers and engineers within agile teams. This involves active participation in team rituals, open communication, and shared ownership of product development.

• Design System Advocacy: Collaboration extends to advocating for design consistency and accessibility, working with engineers to ensure components are implemented correctly and consistently across the platform.

• Feedback Culture: Expect a culture where constructive feedback is regularly exchanged, both given and received, to refine designs and improve processes.

📝 Enhancement Note: The core values are highly indicative of Redwood's culture. Candidates should reflect on how their personal work style and professional values align with these principles, particularly "Make Your Own Weather" and "Own the Outcome," which suggest a need for proactive and results-driven individuals. The emphasis on "Obsess over Customer Success" means understanding the end-user of enterprise software is crucial.

⚡ Challenges & Growth Opportunities

Challenges:

• Designing for Complexity: Translating intricate enterprise automation processes into intuitive and user-friendly interfaces for finance and IT professionals presents a significant design challenge.

• Building a Design System from Scratch: Establishing a new design system requires foresight, strategic thinking, and the ability to create scalable, reusable components that will serve a diverse product portfolio. This involves balancing immediate needs with long-term vision.

• Integrating AI Effectively: Leveraging AI tools daily requires continuous learning and adaptation to ensure they genuinely enhance productivity and creativity, rather than becoming a superficial addition. Understanding the ethical implications and limitations of AI in design is also key.

• Balancing Stakeholder Needs: Effectively managing the competing needs and priorities of product management, engineering, and end-users to deliver cohesive and impactful designs.

• Maintaining Design Velocity: Keeping pace with agile engineering sprints while conducting thorough research and design iterations requires strong time management and efficient workflows.

Learning & Development Opportunities:

• Design System Leadership: Opportunity to become a key architect and leader in building Redwood's foundational design system, shaping its future.

• AI in Design Expertise: Develop deep expertise in applying AI tools to UX design, potentially becoming an internal thought leader and evangelist for these technologies.

• Enterprise Software Domain Knowledge: Gain specialized knowledge in ERP, automation, and mission-critical business processes, becoming a highly sought-after expert in this niche.

• Mentorship Growth: Refine leadership and mentorship skills by guiding junior designers and contributing to the overall design maturity of the organization.

• Cross-functional Exposure: Deepen understanding of product strategy, engineering challenges, and customer success imperatives through close collaboration.

📝 Enhancement Note: The challenges are directly tied to the innovative aspects of the role—building a new design system and integrating AI. Success in navigating these challenges will naturally lead to significant growth opportunities and a unique skill set highly valuable in the enterprise UX market.

💡 Interview Preparation

Strategy Questions:

• Design System Philosophy: "Describe your approach to building a design system from the ground up for an enterprise product suite. What are the key considerations for scalability, reusability, and adoption?" Be ready to discuss component libraries, design tokens, and governance.

• AI in Your Workflow: "How have you specifically used AI tools (e.g., ChatGPT, Copilot) in your daily design process? Provide an example of how AI helped you solve a complex design problem or significantly improved your efficiency on a recent project."

• Complex Enterprise UX: "Walk us through a challenging enterprise UX project you led. What made it complex, how did you approach understanding the users (e.g., finance, IT), and what was the outcome?" Focus on your problem-solving process and user empathy.

Company & Culture Questions:

• Redwood's Mission: "What excites you about Redwood's mission to provide 'lights-out automation' for mission-critical business processes?" Show you've researched their core business.

• Core Values Alignment: "Which of Redwood's core values resonates most with you, and how have you demonstrated that value in your previous roles?" Connect your experience to their stated principles.

• On-site Collaboration: "How do you ensure effective collaboration and communication within an on-site team, especially when working with engineers and product managers in an agile setting?"

Portfolio Presentation Strategy:

• Structure for Impact: Organize your presentation logically. Start with a brief overview of your experience, then dive into 2-3 of your strongest, most relevant case studies.

• Focus on Process & Rationale: For each case study, clearly articulate the problem, your specific role, the research methods used, your design decisions and the rationale behind them, the challenges faced, and the measurable outcomes or impact.

• Highlight Design System & AI Elements: Explicitly call out any contributions to design systems or instances where AI tools were leveraged. Be prepared to explain your methodology and the benefits gained.

• Engage Your Audience: Make it a conversation. Ask clarifying questions, invite feedback, and be prepared to defend your design choices with data and user insights.

• Prepare for Q&A: Anticipate questions about your design choices, alternative solutions, technical feasibility, and how you handle disagreements or feedback.

📝 Enhancement Note: Interviewers will be looking for evidence of strategic thinking, hands-on execution, and a proactive, collaborative approach. Demonstrating a clear understanding of enterprise UX challenges, a genuine interest in automation, and practical experience with modern tools like Figma and AI will be critical.

📌 Application Steps

To apply for this Senior UX Designer position at Redwood Software:

• Submit Your Application: Complete the application form via the provided Greenhouse link. Ensure all required fields are accurately filled out.

• Tailor Your Resume: Customize your resume to highlight your 5-7 years of experience in B2B SaaS or enterprise software UX design. Emphasize your skills in Figma, user research, design systems, and AI tool utilization. Use keywords from the job description.

• Curate Your Portfolio: Select 2-3 of your strongest, most relevant case studies that best showcase your end-to-end UX process, experience with complex enterprise applications, and any contributions to design systems. Prepare a clear narrative for each.

• Prepare Your AI Use Cases: Be ready to discuss specific examples of how you've used AI tools to enhance your design productivity, solve problems, or improve workflows during your portfolio presentation and interviews.

• Research Redwood: Thoroughly understand Redwood Software's mission, products (especially RunMyJobs), core values, and the enterprise automation industry. This will help you tailor your responses and demonstrate genuine interest.

• Practice Your Presentation: Rehearse your portfolio walkthrough and practice articulating your design rationale clearly and concisely. Be prepared to answer questions about your process and decision-making.

⚠️ 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.