Lead/Senior Product Designer

📍 Job Overview

Job Title: Lead/Senior Product Designer

Company: Pebl

Location: Toronto, Ontario, Canada

Job Type: FULL_TIME

Category: Product Design & Design Systems

Date Posted: May 11, 2026

Experience Level: Senior (6+ years)

Remote Status: Remote (Canada)

🚀 Role Summary

• Lead the evolution and ownership of Pebl's comprehensive design system, driving its integration with emerging AI technologies to create a cutting-edge, AI-led toolkit.

• Apply a systems-thinking approach to create scalable, consistent, and high-quality user experiences across Pebl's AI-powered Global Work Platform™.

• Partner closely with cross-functional teams, including product management, engineering, and fellow designers, to champion design system adoption and align with strategic product use cases.

• Contribute directly to end-to-end product design initiatives, leveraging and extending the design system to solve complex user problems and enhance overall product velocity.

📝 Enhancement Note: This role is identified as Lead/Senior Product Designer, indicating a significant level of autonomy and strategic contribution. The emphasis on "AI lead system and process" suggests a forward-thinking approach to design operations, requiring candidates to be comfortable with and capable of influencing the integration of artificial intelligence into design workflows and toolkits. The remote nature within Canada implies a need for strong asynchronous communication skills and adaptability to a distributed team environment.

📈 Primary Responsibilities

• Own and continuously evolve Pebl’s design system, encompassing components, patterns, comprehensive documentation, and robust governance frameworks.

• Drive the transformation of the design system from a code-based foundation to a seamless, AI-led toolkit, enhancing efficiency and innovation.

• Collaborate with product, engineering, and design teams to ensure widespread adoption, scalability, and strategic alignment of the design system with diverse product use cases.

• Execute end-to-end product design, applying and extending the design system to resolve user problems and deliver exceptional experiences.

• Proactively identify system gaps through product design work and translate these into reusable patterns, components, and system enhancements.

• Ensure and champion brand consistency, robust accessibility standards, and high-quality user experiences across all Pebl product interfaces.

• Establish and promote best practices for design system usage, contribution models, and streamlined design-to-development workflows.

• Lead strategic initiatives aimed at improving overall design efficiency, accelerating delivery velocity, and fostering cross-team alignment.

• Mentor and guide fellow designers in developing strong systems thinking capabilities and advancing their product design craft.

• Influence product strategy by contributing a systems-based perspective to complex, ambiguous problem spaces, ensuring design coherence and scalability.

📝 Enhancement Note: The responsibilities highlight a dual focus: deep ownership of the design system and direct contribution to product design. The expectation to "shift the process and code based system into a seamless AI lead toolkit" indicates a significant strategic objective for the role, requiring a candidate with foresight and the ability to influence technological direction within design. The emphasis on mentorship suggests a leadership component, even without explicit management duties.

🎓 Skills & Qualifications

Education: Bachelor’s degree in Design, Human-Computer Interaction (HCI), or a related field, or equivalent practical experience.

Experience: Minimum of 6 years of progressive experience in product design, with substantial, demonstrable experience in contributing to or leading design systems.

Required Skills:

• Design Systems Ownership & Evolution: Proven ability to own, manage, and evolve a design system, including component libraries, pattern catalogs, and comprehensive documentation.

• Systems Thinking: A strong capacity for systems thinking, enabling the creation of scalable, consistent, and interconnected design solutions.

• Product Design Craft: Expertise in end-to-end product design, from ideation and user research to high-fidelity prototyping and final implementation.

• AI Integration Acumen: Experience or a strong aptitude for understanding and contributing to the integration of AI within design processes and systems, including AI-led toolkits.

• Cross-functional Collaboration: Exceptional ability to partner effectively with product managers, engineers, and other stakeholders to drive adoption and alignment.

• Accessibility Standards: Deep understanding and practical application of accessibility standards (e.g., WCAG) to ensure inclusive design solutions.

• Design Governance & Best Practices: Experience in establishing and enforcing design governance, setting standards, and defining contribution models.

• Mentorship & Leadership: Demonstrated ability to mentor junior designers and lead initiatives within a design team.

Preferred Skills:

• Experience in a fast-paced, growth-stage technology company.

• Familiarity with AI-driven design tools or platforms.

• Experience with design-to-development handoff and close collaboration with engineering teams on implementation.

• Proficiency in user research methodologies and integrating user feedback into design system improvements.

• Experience influencing product strategy from a design systems perspective.

📝 Enhancement Note: The minimum experience of 6 years, coupled with the "Lead/Senior" title, implies a need for a candidate who can operate with significant autonomy and strategic foresight. The "AI lead system and process" requirement is a key differentiator, suggesting that candidates with experience in emerging design technologies or a strong interest and aptitude for AI integration will be highly valued.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Design System Case Studies: Detailed case studies showcasing your contributions to or ownership of a design system, illustrating its evolution, impact, and your specific role in its development (e.g., component creation, pattern definition, documentation updates, governance implementation).

• End-to-End Product Design Projects: Examples of complete product design lifecycles, demonstrating your ability to translate user needs and business requirements into intuitive and effective user interfaces. Highlight the problem, your process, and the measurable outcomes.

• System Thinking in Practice: Evidence of how you've applied systems thinking to solve complex product challenges, ensuring consistency, scalability, and maintainability across multiple features or products.

• AI Integration Concepts (if applicable): Any projects or conceptual work demonstrating an understanding of how AI can enhance design systems or product design workflows.

• Collaboration & Workflow Examples: Visualizations or descriptions of how you've collaborated with engineering and product teams, including examples of design-to-development handoff processes and feedback loops.

Process Documentation:

• Design System Governance Models: Examples of how you've documented and enforced design system governance, including contribution guidelines, version control strategies, and review processes.

• Workflow Optimization Initiatives: Documentation or case studies detailing how you've improved design workflows, increased efficiency, or accelerated product delivery through system-based approaches.

• Accessibility & Quality Assurance: Evidence of processes implemented to ensure design consistency, accessibility compliance, and overall quality across the product suite.

📝 Enhancement Note: Given the emphasis on design systems and the forward-looking AI integration, candidates should be prepared to showcase not just finished designs but also the processes and systems they've built or improved. Demonstrating strategic thinking about scalability, consistency, and the future of design tools will be critical.

💵 Compensation & Benefits

Salary Range: Based on industry benchmarks for Lead/Senior Product Designers in Toronto, Canada, with 6+ years of experience and remote capabilities, the estimated salary range is CAD $110,000 - $150,000 annually. This estimate considers the cost of living in Toronto, the specialized nature of design systems and AI integration, and the seniority of the role.

Benefits:

• Flexible Time Off: Generous policy allowing employees to take the time they need to recharge and maintain work-life balance.

• Parental Leave: Comprehensive support for new parents, facilitating bonding and adjustment during a significant life event.

• Health and Dental Insurance: Robust coverage plans to ensure the well-being of employees and their dependents, applicable where local regulations permit.

• Retirement Savings + Employee Incentive Plan: Opportunities for long-term financial planning and wealth building through retirement savings programs and participation in employee incentive schemes, aligning personal success with company growth.

Working Hours: A standard 40-hour work week is expected, with flexibility to accommodate remote work arrangements and project demands. Core collaboration hours will likely be established to facilitate team synchronization across different time zones within Canada.

📝 Enhancement Note: The salary range is an estimate based on industry data for similar roles in Toronto, Canada, considering the experience level and specialized skills in design systems and AI. The actual compensation will be determined by the candidate's specific qualifications, experience, and internal equity. Benefits are detailed as per the job description, with an emphasis on their relevance to supporting a distributed workforce.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology, SaaS (Software as a Service), Global Employment Solutions. Pebl operates within the rapidly evolving FinTech and HR Tech sectors, providing a platform that simplifies international hiring and payroll. This context demands innovation, agility, and a deep understanding of compliance complexities in a global market.

Company Size: Growing, likely between 50-250 employees, indicated by the need for a Lead/Senior Product Designer to own and evolve a design system. This size suggests a dynamic environment where individual contributions have a high impact.

Founded: Pebl's founding date is not explicitly stated, but the mention of "more than a decade of compliance leadership" implies a company with established expertise and a track record in its field, likely founded in the early to mid-2010s.

Team Structure:

• Product Design Team: The role reports into a Product Design team, which includes other designers. This designer will be a senior member, likely influencing design strategy and best practices.

• Cross-functional Collaboration: Close partnership with Product Management and Engineering is a core expectation. This implies a collaborative, integrated product development process.

• Reporting Hierarchy: While not explicitly stated, a Lead/Senior Designer often reports to a Head of Product Design or a Director of Product, with potential for direct mentorship of junior designers.

Methodology:

• AI-Powered Platform Development: A core methodology involves leveraging AI to enhance the Global Work Platform™, impacting everything from hiring to compliance.

• Agile Product Development: Likely follows agile principles, emphasizing iterative development, rapid feedback, and continuous improvement.

• Design Systems as a Core Enabler: The design system is positioned not just as a UI library but as a strategic tool for efficiency, consistency, and innovation, with a future focus on AI integration.

Company Website: https://hellopebl.com/

📝 Enhancement Note: Pebl's focus on "Purpose in Every Position" and "Where Your Work Moves the Needle" suggests a culture that values impact, accountability, and proactive contribution. The emphasis on global growth and compliance in a complex market implies a need for meticulousness and strategic thinking within all roles, including design. The integration of AI into their platform is a significant differentiator, making this role particularly interesting for designers interested in future-forward technologies.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned as a Lead/Senior Product Designer, signifying a high level of individual contribution and strategic influence within the design function. It's a role for experienced professionals who can not only execute design tasks but also shape design processes, systems, and team capabilities.

Reporting Structure: The designer will likely report to a Head of Product Design or a similar leadership role. They will collaborate closely with Product Managers and Engineering Leads, acting as a key voice in product development discussions. The role also includes a mentorship component, suggesting potential for indirect leadership.

Operations Impact: The designer's impact will be multifaceted:

• Product Experience: Directly shaping the user experience of Pebl's Global Work Platform™, making it more intuitive, efficient, and compliant for businesses worldwide.

• Design Efficiency: Improving the productivity and consistency of the entire design and engineering team through a well-maintained and evolving design system.

• Strategic Influence: Contributing to product strategy by bringing a systems-level perspective, ensuring scalability and long-term vision are considered in design decisions.

• AI Integration: Pioneering the integration of AI into design workflows, positioning Pebl at the forefront of design technology.

Growth Opportunities:

• Design Leadership: Potential to grow into a Design System Manager, Head of Product Design, or similar leadership roles, overseeing broader design initiatives and teams.

• Specialization in AI Design: Deepen expertise in AI-driven design, becoming a subject matter expert in this emerging field within the company.

• Strategic Product Influence: Take on more responsibility in shaping product roadmaps and influencing business strategy through design insights.

• Cross-functional Mobility: Develop strong relationships and understanding across Product, Engineering, and potentially Marketing/Sales, opening doors to broader roles within the tech organization.

📝 Enhancement Note: The "Lead/Senior" title combined with the ownership of a design system and the forward-looking AI integration points towards significant career growth potential. Candidates should be prepared to articulate how they see themselves growing within such a strategic role and how they can contribute to the company's long-term vision.

🌐 Work Environment

Office Type: This is a remote position within Canada, meaning the primary "office" is the employee's home workspace. However, Pebl may facilitate occasional in-person team meetups or offsites, especially given their global focus.

Office Location(s): While the role is remote, the requirement for candidates to be based in Canada suggests a focus on Canadian employment law and potentially aligning with specific time zones for core collaboration. The company headquarters are likely in North America, but the remote nature allows for talent acquisition across Canada.

Workspace Context:

• Remote Collaboration Tools: Expect heavy reliance on digital collaboration tools (e.g., Slack, Zoom, Miro, Figma) for communication, design ideation, and project management.

• Design System Hub: The design system will serve as a central hub for design assets, documentation, and best practices, accessible to all product teams.

• Cross-Functional Interaction: Regular virtual meetings and asynchronous communication channels will facilitate interaction with product managers, engineers, and other designers globally.

Work Schedule: The role operates on a standard 40-hour work week. While remote, establishing core working hours for synchronous collaboration within Canadian time zones (e.g., EST, PST) will be crucial to ensure effective teamwork and timely responses across different departments and potentially with international clients.

📝 Enhancement Note: The remote nature of the role requires a high degree of self-discipline, proactivity in communication, and comfort with digital collaboration tools. Candidates should highlight their experience working effectively in distributed teams and their strategies for maintaining connection and productivity.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A brief call with a recruiter to assess general fit, experience, and alignment with the role's core requirements.

• Portfolio Review & Design Challenge: A deeper dive with the hiring manager or design lead. This will likely involve presenting your portfolio, discussing specific design system case studies, and potentially engaging with a design challenge. The challenge might focus on extending the existing design system or addressing a product problem with a systems-thinking approach.

• Cross-functional Interviews: Meetings with key stakeholders from Product Management and Engineering to evaluate collaboration skills, technical understanding, and ability to integrate design into development workflows.

• Final Interview: A conversation with a senior leader (e.g., Head of Product, CTO) to discuss strategic vision, cultural fit, and long-term impact.

Portfolio Review Tips:

• Highlight Design Systems Expertise: Dedicate a significant portion of your portfolio to design systems work. Clearly articulate your role, the system's architecture, its impact on efficiency, and how you managed its evolution.

• Showcase Systems Thinking: For product design examples, emphasize how you applied a systems-level approach to ensure consistency, scalability, and maintainability, even for individual features.

• AI Integration Focus: If you have any experience or conceptual ideas regarding AI in design, be prepared to discuss them, especially in relation to how it could enhance design systems or workflows.

• Quantify Impact: Wherever possible, use metrics to demonstrate the impact of your work—e.g., reduction in design/development time, increase in design consistency scores, adoption rates of design system components.

• Demonstrate Collaboration: Include examples or explanations of how you've worked with engineering to bring designs to life, highlighting your understanding of the development process.

Challenge Preparation:

• Understand Pebl's Product: Research Pebl's Global Work Platform™ thoroughly. Understand its core value proposition, target audience, and key features.

• Focus on Systems: If the challenge involves a product design task, think about how the solution can be integrated into or extend an existing design system. Consider scalability and consistency.

• AI-Forward Thinking: If the challenge touches upon AI, consider how AI could augment the proposed solution or process.

• Structure Your Approach: For any problem-solving task, clearly articulate your process: understanding the problem, research, ideation, design, testing, and iteration.

📝 Enhancement Note: The interview process is likely to be thorough, focusing on both the craft of design and the strategic impact of a design system lead. Candidates should prepare to discuss their experience with AI integration in design, as this is a key differentiator for Pebl.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: Expected to be the primary design tool for UI design, prototyping, and design system management. Proficiency in creating and managing component libraries, variants, auto layout, and interactive prototypes is essential.

• Design System Platforms: Experience with tools that support design system documentation and sharing (e.g., Zeroheight, Storybook, or internal documentation platforms).

• Prototyping Tools: Beyond Figma, familiarity with tools like InVision or Principle might be beneficial for advanced prototyping.

Analytics & Reporting:

• Product Analytics Tools: Experience with tools like Amplitude, Mixpanel, or Google Analytics to understand user behavior and inform design decisions.

• User Feedback Platforms: Familiarity with tools for collecting and analyzing user feedback (e.g., UserTesting.com, Hotjar, surveys).

CRM & Automation:

• Collaboration & Communication: Slack for real-time messaging and team communication, Jira for issue tracking and project management, Confluence for documentation.

• Whiteboarding & Ideation: Miro or Mural for collaborative brainstorming, user flow mapping, and workshop facilitation, especially in a remote setting.

📝 Enhancement Note: The emphasis on a "seamless AI lead toolkit" suggests that Pebl is looking for a designer who is not only proficient with current industry-standard design tools but also forward-thinking about how AI can be integrated into the design technology stack to enhance efficiency and innovation.

👥 Team Culture & Values

Operations Values:

• Purpose-Driven: A strong belief that every role contributes to a larger mission, driving impact and meaning in the work. This translates to a focus on delivering value that genuinely helps businesses grow globally.

• Accountability & Impact: A culture where individuals are empowered and expected to take ownership of their work and deliver measurable results. This means being proactive, results-oriented, and committed to the success of Pebl's platform.

• Global Mindset & Inclusivity: A commitment to diversity, equity, and inclusion, reflecting the company's mission to connect global talent. This means valuing diverse perspectives and fostering an environment where everyone can thrive.

• Agility & Innovation: Operating in a fast-paced, evolving market requires adaptability, a willingness to experiment, and a drive to innovate, particularly with the integration of AI into their platform.

• Collaboration & Teamwork: A "team-first" mentality, emphasizing strong partnerships across departments to achieve common goals, especially between design, product, and engineering.

Collaboration Style:

• Cross-functional Partnership: Expect close collaboration with Product Management and Engineering, characterized by open communication, shared ownership, and iterative feedback loops.

• Design System as a Shared Resource: The design system is viewed as a collaborative asset, requiring input and buy-in from various teams to ensure its relevance and adoption.

• Mentorship & Knowledge Sharing: A culture that encourages sharing knowledge and mentoring colleagues, fostering collective growth and expertise, particularly in system design and product craft.

📝 Enhancement Note: The company's stated values – "Purpose in Every Position" and "Where Your Work Moves the Needle" – indicate a high-performance culture that values initiative, impact, and a strong sense of mission. For a Lead/Senior Product Designer, this means being ready to take ownership, drive strategic initiatives, and contribute to a culture of continuous improvement and innovation, particularly around AI integration.

⚡ Challenges & Growth Opportunities

Challenges:

• Evolving AI Integration: Navigating the complexities of integrating AI into a design system and product design workflows, which is a nascent and rapidly changing field. This requires continuous learning and adaptation.

• Balancing Systemic Consistency with Product Needs: Effectively managing the inherent tension between maintaining a cohesive design system and allowing for the flexibility needed to address unique product requirements and user contexts.

• Driving Adoption Across Teams: Ensuring widespread adoption and effective utilization of the design system across multiple product teams, overcoming potential resistance or differing priorities.

• Remote Collaboration & Alignment: Maintaining strong team cohesion, effective communication, and consistent design quality in a fully remote, potentially globally distributed team environment.

Learning & Development Opportunities:

• Deep Dive into AI in Design: Opportunities to become an expert in applying AI to design systems, user experience, and product development processes.

• Strategic Design Leadership: Developing skills in influencing product strategy, leading design initiatives, and potentially mentoring junior designers, paving the way for future leadership roles.

• Industry Best Practices: Exposure to cutting-edge design system methodologies and AI technologies through collaboration and potentially industry events or training.

• Global Product Impact: Contributing to a platform that enables global business growth, offering a unique perspective on international user needs and compliance.

📝 Enhancement Note: The primary challenge lies in shaping the future of design at Pebl by integrating AI into their design system. This presents a significant growth opportunity for a designer eager to work at the forefront of technological advancements in the design field. Candidates should be prepared to discuss how they approach ambiguity and drive innovation.

💡 Interview Preparation

Strategy Questions:

• "How would you approach evolving our design system to incorporate AI-driven capabilities, and what are the key considerations for such a transition?" (Focus on process, tools, and strategic impact)

• "Describe a time you had to advocate for design system adoption within a team or organization. What challenges did you face, and how did you overcome them?" (Focus on collaboration, communication, and influencing skills)

Company & Culture Questions:

• "Based on your understanding of Pebl, how do you see the company's mission and values influencing your approach to design?" (Demonstrate research and cultural alignment)

• "How do you stay current with emerging trends in design, technology, and particularly AI in design?" (Showcase continuous learning and proactivity)

Portfolio Presentation Strategy:

• Structure Your Narrative: Begin with your design system contributions, detailing its architecture, governance, and impact. Then, present product design case studies, clearly articulating the problem, your process, and the outcomes, highlighting how the design system was leveraged.

• Quantify Your Impact: Use data and metrics wherever possible to showcase the success of your design system initiatives and product designs (e.g., efficiency gains, consistency improvements, user satisfaction scores).

• Highlight Systems Thinking: For each project, explain how you considered scalability, maintainability, and consistency.

• Discuss AI Opportunities: Be prepared to discuss your vision for AI integration within design and how your experience or ideas could benefit Pebl.

• Engage in Dialogue: Treat the portfolio review as a conversation. Be ready to answer in-depth questions about your design decisions, collaboration process, and problem-solving approach.

📝 Enhancement Note: The interview process will likely assess not only design skills but also strategic thinking, leadership potential, and adaptability to emerging technologies like AI. Candidates should prepare to articulate a clear vision for how design systems, coupled with AI, can drive business value at Pebl.

📌 Application Steps

To apply for this Lead/Senior Product Designer position:

• Submit your application through the provided link on Ashby.

• Curate Your Portfolio: Tailor your portfolio to prominently feature your design systems work and end-to-end product design projects. Emphasize case studies that demonstrate systems thinking, AI integration potential, and quantifiable impact.

• Optimize Your Resume: Highlight your 6+ years of experience, specific contributions to design systems, and any experience with AI in design. Use keywords such as "Design Systems," "Product Design," "Systems Thinking," and "AI-driven Design."

• Prepare Your Narrative: Practice articulating your design process, career achievements, and vision for design systems and AI integration at Pebl. Be ready to walk through your portfolio with confidence.

• Research Pebl: Thoroughly understand Pebl's mission, product, target market, and company values to articulate how your skills and approach align with their goals and culture.

⚠️ 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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