Design Manager, UX Design Team

📍 Job Overview

Job Title: Design Manager, UX Design Team

Company: Redwood Software

Location: Ontario, Canada

Job Type: Full-time

Category: UX Design / Product Design Management

Date Posted: February 05, 2026

Experience Level: 5-10 years (with 2+ years management experience)

Remote Status: On-site

🚀 Role Summary

• Lead and grow Redwood's UX Design team, focusing initially on the RunMyJobs product.

• Establish and champion design excellence, driving the creation of a comprehensive design system from the ground up.

• Ensure the enterprise automation platform delivers exceptional user experiences through user-centered design practices.

• Partner with Product Management and Engineering leadership to integrate UX best practices into the agile product development lifecycle.

• Manage, mentor, and develop a team of UX designers, fostering a high-performing and collaborative design culture.

📝 Enhancement Note: This role is pivotal in shaping the user experience of Redwood's enterprise automation platform. While the primary focus is UX Design Management, the emphasis on building a design system from scratch and the requirement for hands-on design contributions suggest a "player-coach" dynamic. Candidates must demonstrate strong leadership capabilities alongside deep practical UX design expertise. The explicit mention of AI tools indicates a forward-thinking approach to design workflows.

📈 Primary Responsibilities

• Team Leadership & Management: Build, manage, mentor, and conduct performance reviews for a team of UX designers, making hiring and personnel decisions. Foster a collaborative design culture aligned with Redwood's core values, removing blockers and balancing team workload.

• Design Strategy & Execution: Drive end-to-end UX design for RunMyJobs features, establish seamless design processes within agile development, and champion user-centered design principles. Partner with product management on feature requirements and ensure design quality and timely delivery.

• Design System & Standards: Lead the creation and evolution of Redwood's design system, defining component libraries, interaction patterns, and design tooling strategy. Ensure accessibility, consistency, and scalability across all design solutions.

• User Research & Insights: Establish and integrate user research practices, planning and conducting activities like interviews and usability tests to inform product decisions and build empathy across teams. Synthesize findings into actionable recommendations.

• Cross-Functional Collaboration: Partner with product management and engineering leadership on roadmap planning, represent UX perspectives in strategic discussions, and collaborate with marketing and customer success on design-related initiatives.

• AI Integration: Leverage AI tools daily to enhance team productivity, design exploration, and workflow efficiency, establishing best practices for AI usage within the design team.

📝 Enhancement Note: The responsibilities clearly define a strategic leadership role with significant hands-on involvement. The emphasis on "building from the ground up" for the design system and establishing research practices indicates a need for a proactive, foundational approach. The AI integration requirement is a key differentiator, suggesting that candidates with experience in leveraging AI for design efficiency will be highly valued.

🎓 Skills & Qualifications

Education: Bachelor's degree in Design, HCI, or a related field (or equivalent practical experience).

Experience:

• 5-7 years of UX design experience.

• 2+ years of experience managing and mentoring UX designers.

• Proven track record of building or scaling design teams and establishing design practices.

• Deep experience designing complex B2B SaaS or enterprise software products.

• Experience building or contributing significantly to design systems at scale.

• Demonstrated ability to balance hands-on design work with people management responsibilities.

Required Skills:

• Team Leadership & Mentoring: Ability to build, manage, and develop a high-performing design team, including performance management and career development.

• UX Design Excellence: Strong portfolio showcasing expertise in research, interaction design, and visual design for complex enterprise applications.

• Design Systems: Proven experience creating, scaling, and implementing design systems, including component libraries and style guides.

• User Research: Proficiency in user research methodologies (interviews, usability testing, field studies) and translating insights into actionable design decisions.

• Agile Product Development: Deep understanding of agile methodologies and experience collaborating effectively with product management and engineering.

• Communication & Presentation: Excellent verbal and written communication skills, with the ability to present design strategy and work effectively to executive stakeholders.

• Modern Design Tools: Expert proficiency with Figma; experience evaluating and selecting design tooling.

• AI Tool Proficiency: Daily hands-on experience using AI tools (e.g., ChatGPT, Claude, Copilot, Midjourney) to enhance individual and team productivity and design exploration.

Preferred Skills:

• Experience designing automation, workflow, or developer tools.

• Background in enterprise software domains such as ERP, finance, IT operations, or DevOps.

• Experience establishing AI-powered design workflows for teams.

• Familiarity with front-end technologies and close collaboration with engineers on implementation.

• Experience with Design Operations (DesignOps) principles and scaling design practices.

• Published work, conference talks, or thought leadership in the UX field.

• Experience working in product-led organizations with strong engineering cultures.

• Track record of recruiting and developing design talent.

📝 Enhancement Note: The required experience level and specific tool proficiencies (Figma, AI tools) are critical. The "player-coach" aspect is reinforced by the need to balance hands-on design with management. Preferred skills highlight a strong desire for candidates with domain expertise in automation and enterprise software.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Design Leadership & Team Building: Showcase examples of how you've built, managed, or mentored design teams, including process improvements you've implemented for team efficiency and quality.

• Design System Development: Provide detailed case studies of your involvement in creating or significantly evolving a design system, highlighting its impact on consistency, scalability, and development velocity.

• End-to-End UX Design: Demonstrate a complete product design process from research and ideation through to detailed interaction and visual design, specifically for complex B2B SaaS or enterprise applications.

• User Research Integration: Illustrate how you've used user research insights to drive significant product decisions and improve user experience, providing examples of research methodologies applied and outcomes achieved.

• AI Tool Application: Include examples or a specific section detailing how you've leveraged AI tools to enhance your design process, team productivity, or design exploration, quantifying the benefits where possible.

Process Documentation:

• Design Process Frameworks: Be prepared to discuss and demonstrate your experience with establishing and refining design processes, particularly within agile environments, outlining how you ensure seamless integration with engineering workflows.

• Design System Governance: Document your approach to managing and governing a design system, including collaboration mechanisms with engineering, version control strategies, and processes for contribution and evolution.

• User Research Synthesis: Present how you synthesize qualitative and quantitative user research data into actionable insights and present them to stakeholders to influence product strategy and design direction.

• AI Workflow Integration: Outline a methodology for integrating AI tools into daily design workflows, including best practices for prompt engineering, ethical considerations, and measuring the impact on design output and efficiency.

📝 Enhancement Note: The portfolio is crucial for this role, especially for demonstrating leadership in building design systems and teams. Explicitly showcasing AI tool usage in the portfolio is a strong differentiator. Candidates should be prepared to discuss methodologies for process governance and integration, particularly for design systems and AI workflows.

💵 Compensation & Benefits

Salary Range: CAD $120,000 - $170,000 annually. (This range is estimated based on similar Design Manager roles in Ontario, Canada, considering the experience level (5-7 years UX, 2+ years management), the company's focus on enterprise SaaS, and the inclusion of specialized skills like AI tool integration and design system leadership. It aims to be competitive within the Canadian tech market for this level of responsibility.)

Benefits:

• Comprehensive health, dental, and vision insurance.

• Generous paid time off (PTO) and holidays.

• Retirement savings plan with company matching.

• Professional development budget for conferences, courses, and certifications.

• Opportunities for career advancement and leadership growth within a growing company.

• Employee Assistance Program (EAP) for mental and emotional well-being.

• Potential for stock options or performance-based bonuses.

Working Hours: Standard full-time position, typically 40 hours per week. While the role is on-site, Redwood Software may offer flexibility for core working hours, allowing for effective collaboration with global teams and personal needs.

📝 Enhancement Note: The salary range is an estimate. Candidates should be prepared to negotiate based on their specific experience, portfolio, and the company's compensation philosophy. The inclusion of a professional development budget and leadership growth opportunities are key benefits for ambitious operations and design leaders.

🎯 Team & Company Context

🏢 Company Culture

Industry: Software / Enterprise Automation. Redwood Software operates in the competitive enterprise software market, specializing in full-stack automation fabric solutions, particularly for ERP systems. This positioning requires a focus on reliability, scalability, and deep understanding of complex business processes.

Company Size: Redwood Software is a growing organization, indicated by the potential for the design team to expand beyond its initial 2 members. This suggests a dynamic environment where new processes can be established and implemented.

Founded: Redwood Software has a history in providing automation solutions, with a strong emphasis on SaaS-based composable platforms. This implies a mature understanding of cloud infrastructure and modern software delivery, while also embracing innovation.

Team Structure:

• The UX Design team, initially comprising 2 designers plus the manager, will work closely with dedicated Product Management and Engineering teams for the RunMyJobs product.

• The Design Manager will report into a senior product or technology leadership role, likely a Director or VP of Product/Engineering.

Methodology:

• Data Analysis & Insights: The company emphasizes understanding customer needs and driving product decisions through data and user insights, a critical focus for the UX team.

• Workflow Planning & Optimization: Redwood's core business is automation, so a culture of optimizing workflows and processes is inherent. This extends to the product development lifecycle and the design process itself.

• Automation & Efficiency Practices: As a leader in automation, the company likely values efficiency and leveraging technology, including AI, to streamline operations and product delivery.

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

📝 Enhancement Note: The company's focus on "lights-out automation" and "mission-critical business processes" implies a need for robust, reliable, and user-friendly design solutions. The core values like "Obsess over Customer Success," "Work the Problem," and "Own the Outcome" should guide candidate behavior and expectations.

📈 Career & Growth Analysis

Operations Career Level: This is a mid-to-senior level management position. It requires proven experience in UX design and a demonstrated ability to lead and grow a team. The role is positioned to establish and scale the UX function, offering significant influence and ownership.

Reporting Structure: The Design Manager will report to senior product or engineering leadership. This structure provides visibility to executive stakeholders and opportunities to influence strategic product direction. The team will consist of 2 UX designers, with potential for growth, allowing for direct management experience and the development of leadership skills.

Operations Impact: The UX Design Manager will have a direct impact on the usability and adoption of Redwood's enterprise automation platform. By ensuring exceptional user experiences and driving design excellence, they will contribute to customer satisfaction, reduce support overhead, and ultimately support revenue growth through improved product adoption and customer retention. The successful implementation of the design system will also significantly impact engineering efficiency and product consistency.

Growth Opportunities:

• Leadership Advancement: Potential to grow into a Director of UX/Product Design role as the team and company scale, overseeing a larger design organization.

• Strategic Influence: Opportunity to shape the product vision and UX strategy for Redwood's core automation platform, influencing the company's direction.

• Design System Ownership: Deepen expertise in design system architecture, governance, and scaling, becoming a recognized leader in this domain.

• AI Design Specialization: Develop expertise in AI-driven design tools and processes, potentially becoming a go-to resource for AI innovation within the organization.

• Cross-functional Leadership: Expand influence across product, engineering, and go-to-market teams, contributing to broader business objectives.

📝 Enhancement Note: This role offers a clear path for career progression from managing a small team to potentially leading a larger design department. The emphasis on establishing foundational elements (design system, research practices) means the impact and growth potential are substantial for the right candidate.

🌐 Work Environment

Office Type: The role is designated as "On-site," indicating a preference for in-office presence for collaboration and team cohesion. This suggests a structured work environment where face-to-face interaction is valued.

Office Location(s): Ontario, Canada. This broad region may encompass several potential office locations, and candidates should confirm the specific site during the interview process. Accessibility and local amenities would be relevant considerations for on-site roles.

Workspace Context:

• Collaborative Environment: Expect a dynamic office setting designed to foster collaboration between UX, Product Management, and Engineering teams. This likely includes shared workspaces, meeting rooms, and informal gathering areas.

• Operations Tools & Technology: Access to industry-standard design tools (Figma is required), AI tools, and potentially project management software will be provided to support the design process.

• Team Interaction: Regular opportunities for team meetings, design critiques, cross-functional syncs, and knowledge-sharing sessions are expected, facilitating a connected and productive atmosphere.

Work Schedule: Standard business hours are expected, typically Monday through Friday. Given the nature of enterprise software and potential global customer base, some flexibility might be accommodated, but the on-site requirement suggests a primary commitment to office-based hours.

📝 Enhancement Note: The "On-site" designation is important. Candidates should be prepared for a physical presence in an office environment in Ontario, Canada. The collaborative nature of the workspace should be leveraged for building strong relationships with product and engineering counterparts.

📄 Application & Portfolio Review Process

Interview Process:

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

2. Hiring Manager Interview: In-depth discussion with the hiring manager (likely a senior product/engineering leader) focusing on leadership experience, strategic thinking, and team management philosophy.

3. Portfolio Review & Design Challenge: A dedicated session where candidates present their portfolio, highlighting key projects, design decisions, and leadership impact. This may be followed by a take-home design challenge or an in-person/virtual whiteboard exercise to assess problem-solving skills and design approach.

4. Team & Stakeholder Interviews: Meetings with potential direct reports (UX Designers), peers (Product Managers, Engineering Leads), and potentially other senior stakeholders to evaluate collaboration, communication style, and cross-functional alignment.

5. Final Interview: Often with a senior executive (e.g., VP of Product, CTO) to confirm strategic alignment and overall fit.

Portfolio Review Tips:

• Showcase Leadership: Highlight instances where you've mentored designers, improved team processes, or influenced product strategy through design.

• Design System Expertise: Dedicate a section to your experience with design systems, detailing your role in their creation, evolution, and implementation, and the impact achieved.

• B2B SaaS Focus: Emphasize projects involving complex enterprise software, demonstrating your understanding of B2B user needs and workflows.

• AI Integration Examples: Clearly articulate how you've used AI tools in your design process, quantifying benefits like time saved, improved ideation, or enhanced output quality.

• Problem-Solution Narrative: For each project, clearly articulate the problem, your process (including research and AI usage), your solution, and the measurable outcome.

Challenge Preparation:

• Understand the Context: Anticipate challenges related to designing for enterprise automation, workflow management, or complex SaaS interfaces.

• Process-Oriented Thinking: Be ready to discuss how you would approach establishing design processes, building a design system, or integrating user research within an agile framework.

• AI Application: Consider how you would incorporate AI tools into solving the design challenge presented.

• Communication: Practice articulating your design decisions clearly and concisely, explaining your rationale and potential trade-offs.

📝 Enhancement Note: Candidates should prepare to discuss their experience with AI tools extensively, not just as a user, but as a leader who can establish best practices for a team. The portfolio review will be a critical component, so ensure it's tailored to showcase leadership, design systems, and B2B SaaS experience.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: Required for UI/UX design, prototyping, and collaboration. Proficiency is essential.

• AI Design Tools: Daily hands-on experience with tools like ChatGPT, Claude, Copilot, Midjourney, or similar is a must for enhancing productivity and exploration.

• Design System Management Tools: Experience with platforms or methodologies for managing component libraries, style guides, and design tokens.

Analytics & Reporting:

• User Analytics Platforms: Familiarity with tools like Google Analytics, Mixpanel, Amplitude, or similar for tracking user behavior and product engagement.

• Data Visualization Tools: Experience with tools such as Tableau, Power BI, or Looker for presenting user research findings and product performance metrics.

CRM & Automation:

• CRM Systems: Understanding of CRM principles and potential exposure to systems like Salesforce, HubSpot, or similar, as they often integrate with enterprise platforms.

• Workflow Automation Tools: While not directly designing them, an understanding of automation principles is beneficial given Redwood's core business.

📝 Enhancement Note: Figma is explicitly required. The emphasis on "daily hands-on experience" with AI tools means candidates should be prepared to discuss specific tools and how they've integrated them into their workflow and team processes. Familiarity with enterprise software contexts is a strong plus.

👥 Team Culture & Values

Operations Values:

• One Team. One Redwood: Emphasizes collaboration, unity, and shared goals across all departments, including UX.

• Make Your Own Weather: Encourages proactivity, initiative, and taking ownership of challenges and opportunities.

• Obsess over Customer Success: A core driver for all roles, ensuring that customer needs and satisfaction are paramount in design decisions and product development.

• Work the Problem: Focuses on analytical thinking, problem-solving, and a deep dive into understanding issues before jumping to solutions.

• Be Curious: Promotes a learning mindset, encouraging exploration, asking questions, and staying open to new ideas and approaches, especially regarding AI.

• Own the Outcome: Reinforces accountability and responsibility for delivering results, from design execution to team performance.

• Respect Each Other: Fosters a positive and inclusive work environment where diverse perspectives are valued.

Collaboration Style:

• Cross-functional Integration: Expect a highly collaborative environment where UX designers work closely with product managers and engineers, participating in agile ceremonies and contributing to roadmap planning.

• Process-Oriented Feedback: The culture likely encourages constructive feedback loops for design work, processes, and team dynamics, with a strong emphasis on continuous improvement.

• Knowledge Sharing: Opportunities to share best practices, learnings (especially about AI tools), and design principles across the team and wider organization.

📝 Enhancement Note: Candidates should align their responses and portfolio examples with these core values. Demonstrating a proactive, customer-obsessed, and problem-solving approach, coupled with a collaborative and curious mindset, will be key to cultural fit.

⚡ Challenges & Growth Opportunities

Challenges:

• Building from Scratch: Establishing a comprehensive design system and robust user research practices for the first time within the organization requires significant foundational work and strategic planning.

• AI Integration Strategy: Defining and implementing effective AI usage best practices for a design team, balancing innovation with quality and ethical considerations.

• Cross-functional Alignment: Ensuring consistent adoption of UX best practices and the design system across multiple product and engineering teams, especially in a growing company.

• Balancing Management & Hands-on Work: Successfully managing a team while also contributing hands-on design expertise to support critical product initiatives.

Learning & Development Opportunities:

• Design Leadership Skills: Developing advanced team management, strategic planning, and stakeholder communication skills.

• Design System Architecture: Gaining deep expertise in scaling and governing complex design systems for enterprise products.

• AI in Design: Becoming a thought leader in applying AI to UX design workflows and team productivity within the enterprise software domain.

• Product Strategy Influence: Contributing directly to the strategic direction of Redwood's core automation platform.

• Mentorship: Opportunity to mentor and develop junior and mid-level designers, fostering their growth.

📝 Enhancement Note: Candidates should view the "challenges" as opportunities to demonstrate their problem-solving skills and strategic thinking. Highlighting how they would overcome these initial hurdles will be crucial. The growth opportunities are significant, especially for those looking to step into a more impactful leadership role.

💡 Interview Preparation

Strategy Questions:

• "Describe your philosophy on building and scaling a UX design team from the ground up. What are the first three steps you would take?" (Focus: Leadership, Process Building)

• "How would you approach establishing a design system for an enterprise SaaS product? What are the key components, governance models, and metrics for success?" (Focus: Design Systems, Scalability)

• "Walk us through a complex B2B SaaS product you designed. What was the problem, your approach, how did you leverage user research and AI, and what was the outcome?" (Focus: Hands-on Design, Research, AI Application, ROI)

• "How do you foster a user-centric culture within product and engineering teams? Provide examples of how you've integrated user insights into product decisions." (Focus: User Advocacy, Cross-functional Influence)

Company & Culture Questions:

• "How do Redwood's core values (e.g., 'Obsess over Customer Success', 'Make Your Own Weather') align with your leadership and design approach?" (Focus: Cultural Fit)

• "How would you integrate AI tools into the daily workflow of your design team to enhance productivity and innovation?" (Focus: AI Strategy, Team Management)

• "Describe your experience collaborating with product management and engineering in an agile environment." (Focus: Collaboration, Agile Methodology)

Portfolio Presentation Strategy:

• Structure: Organize your presentation logically, typically starting with an overview of your leadership experience, followed by 2-3 in-depth case studies.

• Case Study Depth: For each case study, clearly outline the problem, your role, the process (research, ideation, design, AI usage), your specific contributions, the solution, and quantifiable results (e.g., increased adoption, reduced task time, improved satisfaction scores).

• Highlight Leadership: Ensure your portfolio demonstrates not just individual design skill but also your ability to guide teams, influence strategy, and implement processes.

• AI Demonstration: Dedicate a segment to showcasing how you've practically applied AI tools in your design process. Be ready to discuss specific prompts, tools, and outcomes.

• Conciseness: Be mindful of time. Focus on the most impactful projects and be prepared to answer questions deeply rather than covering every detail superficially.

📝 Enhancement Note: Candidates should anticipate questions that probe their understanding of enterprise software, their strategic approach to building a design function, and their practical experience with AI tools. The portfolio presentation is a key opportunity to showcase all these aspects.

📌 Application Steps

To apply for this Design Manager position:

• Submit your application through the Redwood Software careers portal via the provided Greenhouse link.

• Tailor Your Resume: Highlight your experience in UX design management, building design systems, B2B SaaS product design, user research, and your hands-on experience with AI design tools. Quantify achievements where possible.

• Curate Your Portfolio: Ensure your portfolio prominently features case studies that demonstrate your leadership, design system experience, complex B2B SaaS projects, and practical application of AI tools in the design process. Structure it to tell a clear story of problem, process, solution, and impact.

• Prepare for Interview Questions: Practice articulating your leadership philosophy, design strategy, and how you would approach the challenges of building a design function and design system at Redwood. Be ready to discuss your experience with AI tools in detail.

• Research Redwood Software: Understand their mission, products (especially RunMyJobs), core values, and their position in the enterprise automation market. This will help you tailor your responses and demonstrate genuine interest.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and industry-standard assumptions for a Design Manager role in Ontario, Canada. This information is intended to provide a comprehensive overview and preparation guide. Specific details regarding salary, benefits, and interview process should be confirmed directly with Redwood Software during the application and interview stages.