Staff Product Designer

📍 Job Overview

Job Title: Staff Product Designer

Company: Diligent Corporation

Location: Vancouver, British Columbia, Canada

Job Type: Full-time

Category: Product Design / User Experience (UX)

Date Posted: February 10, 2026

Experience Level: 5-10 Years

Remote Status: Hybrid (at least 50% in-office time)

🚀 Role Summary

• Lead the end-to-end design strategy for Platform AI and Core Services crucial for the Diligent One Platform, focusing on AI-native workflows and shared capabilities.

• Define and evolve reusable design foundations and system-level experiences that enable other product teams to deliver high-quality AI features efficiently and consistently across the entire product suite.

• Operate as a lead on complex, ambiguous, and multi-product initiatives, taking ownership of vision and execution for entire systems rather than isolated features.

• Drive product strategy in close partnership with Product Management and Engineering, translating intricate problems into elegant solutions and aligning design decisions with measurable success metrics.

📝 Enhancement Note: This role is positioned as a senior individual contributor with significant influence over platform-level design strategy and execution, particularly within the emerging domain of AI-driven product experiences. The emphasis on "system-level experiences" and "reusable design foundations" indicates a focus on scalability, consistency, and efficiency across multiple product teams, which is critical in enterprise SaaS environments.

📈 Primary Responsibilities

• Lead end-to-end design for critical platform AI and core services that underpin various products within the Diligent One Platform ecosystem.

• Ensure consistent, high-quality user experiences by applying systems-minded interaction design principles, a refined visual language, and leveraging accessible, production-ready UI components.

• Define, document, and evolve reusable design patterns in close collaboration with the dedicated Design System team, ensuring seamless integration and adoption across product teams.

• Shape product strategy and roadmap in partnership with Product Management and Engineering by effectively framing complex problems, exploring diverse solution spaces, and articulating how design decisions contribute to defined success metrics.

• Pioneer and evangelize AI-native ways of working within Design, Product, and Engineering functions, leveraging AI tools to accelerate exploration, prototype complex workflows, and inform more robust product decisions.

• Mentor and empower other designers by providing clear direction, constructive feedback, and establishing systems that elevate the overall quality and efficiency of design output across the team.

• Collaborate deeply with engineering teams to ensure the feasibility and high-fidelity implementation of designed solutions, balancing user needs with technical constraints.

• Advocate for user-centered design principles and best practices across cross-functional teams, ensuring user needs are at the forefront of platform development.

📝 Enhancement Note: The responsibilities highlight a strategic leadership role focused on platform-level design, system thinking, and the integration of AI. The emphasis on "pioneering AI-native ways of working" suggests this role is at the forefront of an evolving design practice within the company.

🎓 Skills & Qualifications

Education:

Experience:

• Demonstrated track record of significant impact in B2B or enterprise SaaS environments, particularly with complex, data-rich workflows.

• Proven experience leading design initiatives across multi-team or multi-product programs, showcasing systems-level thinking and the ability to manage ambiguity.

• Hands-on experience designing AI-powered user experiences, such as AI assistants, copilots, generative workflows, recommendation engines, or conversational interfaces.

Required Skills:

• Systems Thinking & Design: Ability to think holistically about user flows, information architecture, states, and edge cases across interconnected products and services.

• Interaction Design: Expertise in crafting intuitive, efficient, and engaging user interactions for complex enterprise applications.

• Visual Design: Strong aesthetic sensibility and proficiency in creating polished, production-ready visual interfaces that align with brand guidelines and enhance usability.

• Prototyping: Proficiency in creating interactive prototypes using tools like Figma, Sketch, Adobe XD, or similar, to effectively communicate design concepts and user flows.

• Collaboration & Communication: Exceptional ability to articulate design decisions, facilitate discussions, and build consensus with Product Management, Engineering, and other stakeholders.

• Mentorship: Proven ability to guide, support, and provide constructive feedback to fellow designers, helping them grow and improve their craft.

• AI Product Design: Practical experience designing for AI-driven features and understanding the unique challenges and opportunities they present.

• Accessibility: Solid understanding of WCAG 2.1/2.2 AA guidelines and the ability to integrate accessibility considerations into both product design and design system work.

Preferred Skills:

• Design System Governance: Hands-on experience in creating, evolving, or governing design systems, including component libraries and pattern documentation.

• Domain Expertise: Background or familiarity with governance, risk, compliance (GRC), fintech, or other high-stakes, regulated industries.

• User Research: Experience conducting or collaborating on user research to gather insights and validate design decisions.

• Agile Methodologies: Familiarity with working within Agile/Scrum development processes.

📝 Enhancement Note: The required experience emphasizes impact in B2B/enterprise SaaS and AI-powered experiences, aligning with Diligent's core business. The explicit mention of "systems-minded thinking" and "design systems" indicates a strong need for designers who can contribute to scalable and maintainable design frameworks.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Demonstrated System-Level Impact: Showcase projects that clearly illustrate your ability to design cohesive experiences across multiple products or complex systems, rather than isolated features. Focus on how your work created consistency and efficiency.

• AI-Driven Design Case Studies: Include at least one detailed case study focusing on an AI-powered feature or workflow you designed. Explain the problem, your approach to leveraging AI, the user challenges addressed, and the resulting impact.

• Design System Contribution: Highlight any contributions to or significant usage of design systems. Detail how you utilized or influenced design system components and patterns to ensure consistency and speed up development.

• Problem Framing & Solution Exploration: Present examples where you effectively framed ambiguous problems, explored multiple design directions, and ultimately landed on a well-reasoned, impactful solution. Clearly articulate your decision-making process.

• Metrics & Outcomes: Quantify the impact of your work whenever possible. Showcase how your designs led to measurable improvements in user adoption, efficiency, task completion rates, or other relevant business/product metrics.

Process Documentation:

• Workflow Design & Optimization: Be prepared to discuss your process for mapping out complex user journeys and identifying opportunities for optimization, particularly within AI-driven or data-intensive workflows.

• System Implementation & Automation: Explain how you collaborate with engineering to ensure the successful implementation of designed systems and how you leverage design to enable automation and efficiency for users.

• Measurement & Performance Analysis: Discuss your approach to defining success metrics for design initiatives and how you analyze performance post-launch to inform future iterations and improvements.

📝 Enhancement Note: For a Staff Product Designer role, the portfolio must go beyond individual feature design and demonstrate strategic thinking, system-level impact, and a strong understanding of how to scale design within an enterprise context, especially with new technologies like AI.

💵 Compensation & Benefits

Salary Range:

Benefits:

• Flexible Work Environment: Offers adaptability to personal needs and work styles.

• Global Days of Service: Opportunities to contribute to community initiatives, reflecting a commitment to social responsibility.

• Comprehensive Health Benefits: Includes medical, dental, and vision coverage, essential for employee well-being.

• Meeting-Free Days: Dedicated time to focus on deep work and reduce meeting fatigue, promoting productivity.

• Generous Time Off Policy: Ample paid time off to support work-life balance and prevent burnout.

• Wellness Programs: Initiatives aimed at supporting the physical and mental health of employees.

Working Hours:

• The standard working hours are approximately 40 hours per week. As a hybrid role, this includes an expectation of at least 50% in-office time in Vancouver, BC, balancing focused work with collaborative interactions.

📝 Enhancement Note: The salary range is specific to CAD and the Vancouver market. The benefits listed are typical for tech companies, with a slight emphasis on programs that support employee well-being and community engagement. The hybrid work model specifies a minimum in-office commitment.

🎯 Team & Company Context

🏢 Company Culture

Industry: Governance, Risk, and Compliance (GRC) SaaS solutions, with a strong focus on AI integration. Diligent is a leader in providing digital tools that help organizations manage risk, ensure compliance, and improve governance practices.

Company Size: Diligent serves over 1 million users and 700,000 board members, indicating a substantial enterprise client base. The company operates globally with multiple office hubs.

Founded: Diligent was founded with the mission to empower leaders with technology and insights for greater impact and accountability. This foundation in "modern governance" suggests a culture that values strategic thinking, integrity, and the pursuit of impactful solutions.

Team Structure:

• Operations Team: This role is part of the Product Design function, which likely includes UX researchers, UI designers, and potentially design operations specialists. The team collaborates closely with Product Management and Engineering.

• Reporting Structure: As a "Staff" level designer, this individual will likely report to a Design Manager or Director of Product Design. They are expected to operate with a high degree of autonomy and leadership.

• Cross-functional Collaboration: The role is designed for deep collaboration with Product Managers to shape strategy, Engineering to ensure feasibility and implementation, and the Design System team to maintain consistency. Interaction with other product designers is also key for mentorship and knowledge sharing.

Methodology:

• Data Analysis & Insights: Diligent emphasizes data-driven decision-making, suggesting that design choices are informed by user data, analytics, and market research.

• Workflow Planning & Optimization: The company's focus on GRC and AI implies a strong emphasis on designing efficient, streamlined workflows that reduce complexity and risk for users.

• Automation & Efficiency: With AI as a core focus, the company likely prioritizes automation and efficiency in both its product offerings and internal processes.

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

📝 Enhancement Note: Diligent's positioning as an AI leader in GRC means the company culture likely values innovation, a forward-thinking approach to technology, and a deep understanding of complex business needs. The emphasis on "people who think boldly and move fast" suggests a dynamic and potentially fast-paced environment.

📈 Career & Growth Analysis

Operations Career Level:

• Staff Product Designer: This is a senior individual contributor role, typically falling within the top 10-15% of design talent. It signifies a leader in design execution and strategy, capable of handling complex, ambiguous, and cross-functional projects. Staff designers are expected to influence product direction and mentor others, operating with a high degree of autonomy.

Reporting Structure:

Operations Impact:

Growth Opportunities:

• Operations Skill Advancement: Deepen expertise in AI product design, system design, and cross-platform consistency. Opportunity to become a subject matter expert in AI-native user experiences for enterprise GRC.

• Leadership Development: Grow into a Principal Product Designer role, or transition into design management by gaining experience in mentoring, strategic influence, and team enablement.

• Industry Influence: Contribute to shaping the future of GRC software through innovative AI-driven design, potentially leading to speaking opportunities or contributions to industry best practices.

• Cross-Functional Expertise: Develop a strong understanding of business strategy, product roadmapping, and engineering processes within a leading enterprise SaaS company.

📝 Enhancement Note: The "Staff" title indicates a significant level of responsibility and opportunity for growth, moving beyond individual feature ownership to platform-level strategic impact and leadership.

🌐 Work Environment

Office Type: The role is hybrid, requiring at least 50% in-office time at the Vancouver, BC location. This suggests a commitment to fostering collaboration, team cohesion, and spontaneous innovation through in-person interactions.

Office Location(s): Vancouver, British Columbia, Canada. This location is one of Diligent's key global hubs, likely offering a well-equipped and modern workspace.

Workspace Context:

• Collaborative Environment: The hybrid model and emphasis on in-person time suggest an environment that encourages teamwork, brainstorming sessions, and direct mentorship opportunities.

• Operations Tools & Technology: Expect access to industry-standard design tools (Figma, etc.), collaboration platforms (Slack, Teams), and potentially specialized AI tools for design exploration and prototyping. Access to the company's design system will be crucial.

• Team Interaction: The role is designed for close interaction with Product Managers, Engineers, fellow Designers, and potentially stakeholders from GRC, Risk, and Compliance domains.

Work Schedule:

• The role follows a standard professional work schedule of approximately 40 hours per week, with the hybrid model allowing for flexibility in how and where the remaining time is spent, provided it meets the in-office requirement.

📝 Enhancement Note: The hybrid model is a key characteristic, signaling a company that values both focused individual work and the benefits of in-person collaboration. The Vancouver office is a strategic location for Diligent.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A recruiter or hiring manager will review your application and portfolio. Be prepared to articulate your experience and highlight relevant projects.

• Portfolio Review & Conversation: You'll likely have a dedicated session to walk through your portfolio, focusing on 2-3 key projects that demonstrate your capabilities in system design, AI product design, and enterprise SaaS. Expect deep dives into your process, decision-making, and impact.

• Design Challenge/Workshop: A practical exercise, potentially a take-home assignment or a live workshop, to assess your problem-solving skills, design process, and ability to work within constraints or with new information. This may focus on system-level thinking or AI-driven scenarios.

• Cross-Functional Interviews: Meetings with Product Managers and Engineering Leads to assess your collaboration style, ability to frame problems, and technical understanding.

• Leadership/Staff-Level Interview: A final conversation, potentially with a senior design leader or director, to evaluate your strategic thinking, mentorship capabilities, and cultural fit for a Staff-level role.

Portfolio Review Tips:

• Curate Strategically: Select projects that best showcase your experience with complex B2B/enterprise SaaS, AI-powered features, and system-level design. Quantify impact wherever possible.

• Tell a Story: For each project, clearly articulate the problem, your specific role and contributions, your design process (research, ideation, iteration, validation), and the measurable outcomes.

• Highlight Systems Thinking: Demonstrate how you approach design challenges holistically, considering the interconnectedness of features, user flows, and the overall platform experience.

• Showcase AI Expertise: Clearly explain your approach to designing AI-native features, including how you handled user trust, data privacy, and the unique interaction models AI enables.

• Accessibility & Design Systems: Explicitly mention and demonstrate your understanding and application of accessibility principles and design system best practices.

Challenge Preparation:

• Focus on Process: Understand that interviewers will be assessing how you think and solve problems, not just the final solution.

• System Design: Practice thinking about how different components interact and how to create scalable, consistent patterns.

• AI Scenarios: Consider how you would approach designing for AI features, including ethical considerations and user education.

• Communication: Prepare to articulate your thought process clearly and concisely, especially under pressure.

📝 Enhancement Note: The interview process is likely rigorous, typical for a Staff-level role, with a strong emphasis on portfolio depth, strategic thinking, and the ability to lead complex, ambiguous projects.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (highly probable, industry standard for collaboration and design systems), Sketch, Adobe Creative Suite.

• Collaboration & Communication: Slack, Microsoft Teams, Jira, Confluence.

• AI Design Tools: Potentially AI-powered design assistants or tools for rapid prototyping and concept generation (e.g., Midjourney for ideation, AI-assisted wireframing tools).

Analytics & Reporting:

• Tools for analyzing user behavior and product performance (e.g., Google Analytics, Amplitude, Mixpanel, Pendo).

CRM & Automation:

• While not directly a designer's tool, understanding CRM systems (like Salesforce) and automation platforms can provide context for enterprise workflows. Diligent itself is a GRC platform, so familiarity with enterprise software architecture is beneficial.

• Design System Platforms: Tools for managing and distributing design system components and documentation (e.g., Zeroheight, Storybook).

📝 Enhancement Note: Proficiency in Figma and experience with design system management tools are highly likely to be critical. Familiarity with AI tools relevant to the design process is also a key differentiator for this role.

👥 Team Culture & Values

Operations Values:

• Innovation & Bold Thinking: Diligent encourages individuals to "think boldly" and "experiment fearlessly," particularly in leveraging AI to redefine workflows and user experiences.

• Curiosity & Continuous Learning: A strong emphasis on asking big questions, embracing change, and a commitment to ongoing learning, especially in the rapidly evolving field of AI.

• Impact & Purpose: A mission-driven approach to making the world more sustainable, equitable, and better, with a focus on empowering leaders and driving accountability.

• Collaboration & Community: Fostering a global community where people work together to build the future, with an emphasis on connection and shared mission.

• Efficiency & Rigor: Given the GRC domain, there's an implied value placed on precision, thoroughness, and designing robust solutions that manage risk effectively.

Collaboration Style:

• Cross-functional Integration: The role demands tight collaboration across Design, Product, and Engineering, aiming for shared ownership and alignment on strategy and execution.

• Systems-Oriented Approach: Expect a culture that values consistency, reusability, and a holistic view of the product ecosystem, facilitated through design systems and shared patterns.

• Feedback & Mentorship: A culture that supports constructive feedback exchange and mentorship, particularly from senior designers to more junior team members, to elevate the overall quality of work.

📝 Enhancement Note: The company values emphasize innovation, learning, and making a tangible impact, all within a collaborative global framework. For this role, these values translate to pushing boundaries with AI, sharing knowledge, and working effectively across disciplines.

⚡ Challenges & Growth Opportunities

Challenges:

• Navigating Ambiguity: Leading design for complex, multi-product platform initiatives often involves high degrees of ambiguity and evolving requirements, especially in the fast-paced AI space.

• Balancing Platform vs. Product Needs: Effectively designing foundational platform elements that serve diverse product team needs while maintaining a cohesive user experience across the entire suite.

• Pioneering AI-Native Design: Defining new interaction paradigms and user workflows for AI features requires significant exploration, user education, and careful consideration of ethical implications.

• Driving Adoption of Design Systems & Patterns: Ensuring that reusable patterns and AI-native foundations are effectively adopted and utilized by numerous product teams across the organization.

• Mentoring & Raising the Bar: Effectively guiding and mentoring other designers while simultaneously pushing the overall quality and strategic impact of the design practice.

Learning & Development Opportunities:

• AI & Emerging Tech: Deepen expertise in designing for cutting-edge AI technologies and their application in enterprise software.

• Platform Design Strategy: Gain extensive experience in designing for complex, interconnected platforms, understanding the nuances of scalability, consistency, and cross-functional dependencies.

• Leadership & Influence: Develop strategic leadership skills, influencing product direction and mentoring teams within a leading GRC SaaS company.

• Industry Conferences & Certifications: Potential opportunities to attend relevant design and AI conferences, or pursue certifications that enhance skills and industry recognition.

• Cross-Functional Acumen: Enhance understanding of business strategy, product development lifecycles, and engineering challenges in a mature enterprise tech environment.

📝 Enhancement Note: The challenges are inherent to a senior platform design role, especially one focused on emergent AI technologies. The growth opportunities directly address skill development in these critical areas.

💡 Interview Preparation

Strategy Questions:

• "How would you approach designing a new AI assistant for board members to help them quickly synthesize key risks from multiple reports?" (Focus on problem framing, user needs, AI interaction models, and output clarity.)

• "Describe a time you had to influence product strategy through design. What was the situation, your approach, and the outcome?" (Highlight your ability to lead with design, frame problems, and drive decisions with data/rationale.)

Company & Culture Questions:

• "What interests you most about Diligent's mission in GRC and AI?" (Research Diligent's specific products and market position, and connect it to your passion for impactful enterprise solutions.)

• "How do you approach mentoring junior designers and contributing to a positive team culture?" (Share specific examples of your mentorship style and how you foster collaboration.)

Portfolio Presentation Strategy:

• Deep Dive on AI Project: Select your strongest AI-related project. Walk through the problem, your role, the creative process, key design decisions (especially around AI interaction), challenges faced, and the quantifiable impact.

• System Design Example: Present a project that showcases your ability to think holistically about user flows, information architecture, and reusable patterns across a complex system or multiple products.

• Focus on Your "Why": Be ready to articulate why you made specific design choices, backed by research, user needs, or business objectives.

• Be Prepared for Whiteboarding: Have a strategy for how you'll approach a live design exercise, focusing on process, communication, and problem-solving.

📝 Enhancement Note: Preparation should focus on demonstrating strategic thinking, system-level impact, AI design expertise, and strong collaboration skills, aligning with the Staff Product Designer level and Diligent's focus.

📌 Application Steps

To apply for this operations position:

• Submit your application through the Diligent Corporation careers portal.

• Portfolio Customization: Tailor your resume and portfolio to prominently feature your experience in B2B/enterprise SaaS, AI-powered product design, and system-level thinking. Ensure your portfolio clearly demonstrates your ability to lead complex projects and drive measurable impact.

• Resume Optimization: Highlight keywords from the job description, such as "Platform AI," "Core Services," "System-Level Experiences," "Design Systems," "AI-Native Workflows," "Enterprise SaaS," and "Staff Product Designer." Quantify achievements with specific metrics where possible.

• Interview Preparation: Practice articulating your design process, decision-making, and the impact of your work, particularly for AI-focused and system-design projects. Prepare to discuss your approach to mentorship and cross-functional collaboration.

• Company Research: Thoroughly research Diligent's product suite, its position in the GRC market, and its stated values regarding AI and innovation. Understand how your skills can contribute to their mission.

⚠️ 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.