Senior Product Designer - Workleap

📍 Job Overview

Job Title: Senior Product Designer
Company: Workleap
Location: Canada - Remote
Job Type: Full-time
Category: Product Design / User Experience
Date Posted: October 3, 2025
Experience Level: 5-10 Years
Remote Status: Remote Solely

🚀 Role Summary

• Drive the end-to-end product design process within a cross-functional team, ensuring user-centric solutions are delivered rapidly.
• Translate complex, ambiguous problems into intuitive, high-impact user experiences that align with business objectives and user needs.
• Collaborate closely with Product Managers and Tech Leads to influence product strategy, roadmap, and feature definition.
• Leverage AI as a core design material to create innovative and valuable features, moving beyond conventional design approaches.
• Contribute to the ongoing evolution and quality of a robust design system, ensuring consistency and scalability across products.

📝 Enhancement Note: This role is positioned as a 'Senior' Product Designer, implying a need for significant autonomy, strategic input, and the ability to lead design initiatives within a product trio. The emphasis on "moving with urgency," "balancing craft and speed," and "designing with AI as a core material" suggests a fast-paced, innovative environment focused on rapid iteration and the integration of cutting-edge technology.

📈 Primary Responsibilities

• Own the complete design process for assigned features, from initial concept and user research through to final implementation and iteration.
• Develop user flows, wireframes, and high-fidelity prototypes that effectively solve user problems and meet product goals.
• Conduct user research, usability testing, and analyze product metrics to gather insights and inform design decisions.
• Partner with engineering teams to ensure accurate implementation of designs and maintain design quality throughout the development lifecycle.
• Actively participate in design critiques, providing and receiving constructive feedback to elevate design quality and foster a collaborative design culture.
• Contribute to the strategy and roadmap discussions, advocating for user needs and proposing innovative solutions.
• Design and contribute to the evolution of the company's design system to ensure consistency and efficiency across all products.
• Champion the user by advocating for their needs and ensuring their perspective is central to product development.

📝 Enhancement Note: The responsibilities highlight a blend of strategic thinking and hands-on execution. The emphasis on "translating ambiguous problems" and "designing with AI" indicates a need for strong problem-solving skills and adaptability to emerging technologies. The "tight-knit trio" structure with PM and Tech Lead suggests a highly collaborative and integrated product development approach.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a Bachelor's degree in Design, HCI, Computer Science, or a related field, or equivalent practical experience, is typically expected for senior-level roles.

Experience: Minimum of 5+ years of experience designing SaaS products within cross-functional teams, demonstrating a proven track record of shipping impactful features.

Required Skills:

• Product Design Strategy: Ability to influence product vision and roadmap through user-centric design thinking.
• End-to-End Design Process: Proficiency across the entire design spectrum, including user research, strategy, user flows, wireframing, UI design, and interaction design.
• Prototyping & Iteration: Skilled in rapid prototyping and iterative design based on feedback and data.
• User Empathy & Research: Strong user instincts and the ability to deeply understand user needs, especially in ambiguous problem spaces.
• Collaboration: Proven ability to work effectively within cross-functional teams (Product Management, Engineering) and contribute to a collaborative culture.
• Communication: Excellent verbal, written, and visual communication skills, capable of articulating design decisions and rationale clearly.
• Design Systems: Experience contributing to or utilizing design systems for consistency and scalability.
• Agile Methodologies: Familiarity with agile development processes and ability to deliver within a fast-paced, high-velocity environment.
• Attention to Detail: Meticulous approach to execution and a commitment to high-quality design polish.

Preferred Skills:

• AI-Powered Feature Design: Experience designing or working with AI-powered features, understanding their unique design considerations.
• SaaS Product Expertise: Deep understanding of SaaS product paradigms and user expectations.
• User Research Techniques: Advanced proficiency in various user research methodologies.
• Design System Contribution: Experience leading or significantly contributing to the development of a design system.

📝 Enhancement Note: The "5+ years of experience" requirement for SaaS products within cross-functional teams suggests a need for candidates who have navigated complex product development cycles and understand the nuances of B2B software design. The explicit mention of "AI as a core material" indicates a strong preference for candidates who can think innovatively about integrating AI into user experiences.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Comprehensive Case Studies: Showcase 3-5 detailed case studies that demonstrate ownership of the end-to-end design process for SaaS products.
• Problem-Solution Framing: Clearly articulate the problem space, user needs, and how your design decisions addressed them.
• Process Visualization: Illustrate your design process, including user research, wireframing, prototyping, user testing, and iteration.
• Impact Metrics: Quantify the impact of your designs, using metrics such as user engagement, conversion rates, task completion success, or efficiency gains.
• AI Design Examples (Preferred): If available, include examples of designing with AI or for AI-powered features, highlighting your approach.

Process Documentation:

• User Journey Mapping: Demonstrate the ability to map out complex user journeys and identify key touchpoints for improvement.
• Workflow Design: Showcase examples of designing intuitive workflows that simplify user tasks.
• Design System Contribution: If applicable, provide examples of your contributions to or utilization of a design system.
• Iteration & Optimization: Highlight instances where user feedback or data led to significant design iterations and improvements.

📝 Enhancement Note: For a Senior Product Designer role, the portfolio is critical. It needs to go beyond just showcasing final UI and delve into the strategic thinking, problem-solving methodologies, and measurable impact of the candidate's work. The emphasis on "ambiguous problems" and "AI as a core material" means portfolios should highlight how candidates approach uncharted territory and integrate advanced technologies.

💵 Compensation & Benefits

Salary Range: For a Senior Product Designer role in Canada (remote), based on experience levels ranging from 5-10 years and the demand for specialized skills like AI design, a competitive salary range is estimated to be between CAD $100,000 - $150,000 annually. This range can vary based on specific experience, skill set, and the candidate's location within Canada due to cost of living differences, though remote roles often standardize compensation.

Benefits:

• Comprehensive Health Coverage: Including medical, dental, and vision insurance.
• Generous Paid Time Off: Vacation days, personal days, and public holidays.
• Remote Work Stipend: Support for home office setup and ongoing remote work expenses.
• Professional Development: Opportunities for training, conferences, and skill enhancement.
• Stock Options/Equity: Potential for company stock options or equity grants.
• Retirement Savings Plan: Contribution matching for pension or retirement savings plans.
• Work-Life Balance Focus: Emphasis on sustainable work practices and flexible scheduling where possible.
• Parental Leave: Supportive parental leave policies.

Working Hours: A standard full-time work week is typically around 40 hours. Given the remote nature and emphasis on speed, there may be flexibility in daily scheduling, but responsiveness and collaboration during core business hours for the team (likely Eastern Time, given Montreal HQ) are expected.

📝 Enhancement Note: Salary estimates are based on industry benchmarks for Senior Product Designers in Canada, considering the remote work arrangement and the company's stated focus on innovation and AI. Benefits are inferred based on standard offerings for tech companies of Workleap's size and industry, aiming to attract and retain senior talent.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology, Software (HR Tech, IT Management Software)
Company Size: Workleap operates a significant number of employees, likely in the hundreds, given its two major product lines (Workleap Platform and ShareGate) and 20,000+ customer base. This size suggests a structured yet agile environment with established processes but still room for individual impact.
Founded: 2006. This long history indicates stability, experience, and a proven ability to adapt and grow within the tech landscape.

Team Structure:

• Product Trios: Designers work in close-knit, multidisciplinary teams composed of a Product Manager, Tech Lead, and Product Designer. This structure fosters strong collaboration and shared ownership.
• Growing Product Team: The design team is part of a growing, multidisciplinary product organization where designers are considered strategic partners from the outset.
• Remote-First: The company operates on a remote-first model, emphasizing intentional collaboration and communication to ensure team cohesion and productivity.

Methodology:

• Customer-Centric: A strong focus on customer outcomes and user needs guides product development.
• AI-Native Experiences: Explicit goal to design new experiences that leverage AI as a fundamental component.
• Agile & Iterative: The culture supports rapid iteration, learning from feedback, and moving quickly.
• Data-Informed Decisions: Product metrics, user feedback, and behavioral data are used to inform design and product strategy.
• Design System Driven: Commitment to maintaining and evolving a design system for efficiency and consistency.

Company Website: https://workleap.com/

📝 Enhancement Note: Workleap's culture is characterized by a builder's mentality, a focus on simplicity and exceptional value, and a drive for innovation, particularly in AI. The "remote-first" approach requires a high degree of self-motivation and strong communication skills from team members.

📈 Career & Growth Analysis

Operations Career Level: Senior Product Designer. This level signifies a high degree of autonomy, strategic contribution, and the ability to lead design initiatives within a product team. Senior designers are expected to mentor junior colleagues, influence product direction, and tackle complex, ambiguous problems.

Reporting Structure: The Senior Product Designer will report into a Design Lead or Head of Product Design, working closely within a "product trio" (PM, Tech Lead, Designer) on a day-to-day basis. This structure ensures direct collaboration with key decision-makers.

Operations Impact: Senior Product Designers at Workleap are positioned to have a significant impact on revenue and business decisions by:

• Defining Product Strategy: Influencing the roadmap with user-centric insights and innovative design solutions.
• Driving User Adoption & Engagement: Creating intuitive and valuable experiences that lead to higher customer satisfaction and retention.
• Enhancing Product Value: Designing AI-native features that differentiate Workleap's offerings and provide a competitive edge.
• Improving Development Efficiency: Contributing to and utilizing a robust design system that speeds up the development cycle.

Growth Opportunities:

• Leadership in Design: Opportunities to lead design efforts for new product initiatives or feature areas.
• Mentorship: Potential to mentor junior designers and contribute to the growth of the design team.
• Specialization in AI Design: Developing deep expertise in designing cutting-edge AI-powered user experiences.
• Cross-Product Exposure: Working on different product lines (Workleap Platform, ShareGate) to broaden experience.
• Influence on Design System: Taking on greater responsibility for the strategy and evolution of the design system.
• Career Progression: Potential trajectory towards Lead Product Designer, Design Manager, or specialized roles within product strategy.

📝 Enhancement Note: The "Senior" title and the emphasis on strategic influence and AI design indicate that growth opportunities will focus on deepening expertise, taking on more leadership, and contributing to the company's innovative product direction.

🌐 Work Environment

Office Type: Remote Solely. Workleap is a remote-first company, meaning all operations and team interactions are conducted virtually.

Office Location(s): While headquartered in Montreal, Canada, this role is fully remote and can be performed from anywhere within Canada. Specific time zone alignment (e.g., Eastern Time) may be beneficial for synchronous collaboration.

Workspace Context:

• Digital Collaboration: The workspace is entirely digital, relying heavily on tools like Microsoft Teams, Slack, and project management software for communication and collaboration.
• Design Tooling: Access to industry-standard design tools (e.g., Figma, Sketch) and prototyping software is essential.
• Asynchronous Communication: The remote-first model necessitates proficiency in asynchronous communication through written documentation, shared files, and recorded updates.
• Intentional Collaboration: The company emphasizes intentional collaboration, meaning team members are encouraged to schedule and structure interactions purposefully.

Work Schedule: While the role is full-time (approx. 40 hours/week), the remote-first nature offers flexibility in daily scheduling. However, designers must be available for synchronous collaboration during core team hours, likely aligned with Eastern Time, for trio planning, feedback sessions, and sprint ceremonies.

📝 Enhancement Note: The remote-first environment requires candidates to be self-disciplined, proactive in communication, and comfortable with digital collaboration tools. The emphasis on "intentional collaboration" suggests a need for structured communication and proactive engagement.

📄 Application & Portfolio Review Process

Interview Process:

1. Phone Screen: Initial conversation with a recruiter to assess basic qualifications, cultural fit, and interest in the role.
2. Virtual Interview (Microsoft Teams): A deeper dive with the hiring manager and potentially a peer designer. This stage often includes discussing past projects, design philosophy, and approach to problem-solving.
3. Work Sample/Design Challenge: Candidates may be asked to complete a take-home design exercise or a live design challenge. This assesses practical design skills, problem-solving abilities, and how they approach a given problem within a specific timeframe.
4. Job Offer: Following successful completion of all interview stages.

Portfolio Review Tips:

• Highlight AI & Ambiguity: Explicitly showcase projects where you tackled ambiguous problems or designed with AI. Clearly articulate your thought process, challenges, and outcomes.
• Demonstrate Process, Not Just Polish: Show your iterative journey, including research, wireframes, testing, and how feedback shaped the final design.
• Quantify Impact: Use metrics to demonstrate the business and user value of your designs. For example, "Increased user engagement by X%" or "Reduced task completion time by Y%."
• Structure for Clarity: Organize your portfolio logically, with clear headings, visual aids, and concise explanations. Make it easy for reviewers to grasp your contributions and impact.
• Tailor to Workleap: Research Workleap's products (Workleap Platform, ShareGate) and their mission. Frame your experience and portfolio examples to align with their focus on simplicity, AI, and HR/IT solutions.

Challenge Preparation:

• Understand the Context: If given a design challenge, thoroughly understand the problem statement, target users, and business goals.
• Define Your Approach: Outline your methodology before diving into design. This shows strategic thinking.
• Focus on Core Problems: Prioritize solving the most critical user needs and business objectives within the given constraints.
• Communicate Your Rationale: Be prepared to explain your design decisions clearly and defend them with user-centered reasoning.
• Time Management: Practice time management to ensure you can deliver a comprehensive response within the allotted time.

📝 Enhancement Note: The interview process suggests a structured approach to assessing candidates, with a strong emphasis on practical design skills (work sample) and strategic thinking. The portfolio review is likely to be a key component, where candidates must demonstrate their ability to handle complexity and innovative technologies like AI.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (highly probable, industry standard), Sketch, Adobe Creative Suite (Illustrator, Photoshop).
• Collaboration & Communication: Microsoft Teams (explicitly mentioned for interviews), Slack, Zoom.
• Project Management: Jira, Asana, Trello, or similar tools for task tracking and workflow management.

Analytics & Reporting:

• Product Analytics: Amplitude, Mixpanel, Google Analytics, or similar platforms for tracking user behavior and product performance.
• Data Visualization: Tableau, Power BI, or built-in dashboarding tools for presenting data insights.

CRM & Automation:

• CRM: Salesforce, HubSpot (less likely for a pure design role, but understanding is beneficial).
• Automation: Understanding of workflow automation principles within SaaS products.
• Integration: Familiarity with how different tools and systems connect within a SaaS ecosystem.

📝 Enhancement Note: While the job description doesn't explicitly list all tools, a Senior Product Designer in a SaaS company, especially one focused on AI and remote collaboration, would be expected to be proficient in modern design and prototyping tools like Figma, along with standard communication and project management software. Familiarity with analytics tools is also crucial for data-informed design.

👥 Team Culture & Values

Operations Values:

• Simplicity: A core value driving the creation of intuitive and easy-to-use products.
• Customer-Centricity: Deep commitment to understanding and serving user needs.
• Ownership & Initiative: Encouraging individuals to take responsibility and drive projects forward.
• Curiosity: Fostering a desire to learn, explore new ideas, and question the status quo.
• Intentional Collaboration: Valuing thoughtful and structured teamwork.
• Craft & Quality: A dedication to high standards in design execution and product polish.
• Innovation (especially AI): Embracing new technologies and pushing boundaries to create novel experiences.

Collaboration Style:

• Cross-Functional Partnership: Strong emphasis on close collaboration within "product trios" (PM, Eng, Design) and with other stakeholders.
• Open Feedback Culture: Encouraging the open sharing of feedback during design critiques and team discussions.
• Asynchronous & Synchronous Balance: Utilizing both real-time meetings and asynchronous communication methods for effective teamwork in a remote setting.
• Mutual Support: A culture where team members build, trust, and support each other, sharing in both successes and failures.

📝 Enhancement Note: The company culture at Workleap is built around a passion for making work simpler, a commitment to innovation (particularly AI), and a collaborative, supportive environment. These values are crucial for candidates to understand to assess cultural fit and align their approach.

⚡ Challenges & Growth Opportunities

Challenges:

• Designing for Ambiguity: Tackling complex, ill-defined problems and translating them into clear, user-friendly solutions.
• Integrating AI Effectively: Moving beyond superficial AI features to create genuinely valuable, AI-native experiences that users understand and trust.
• Balancing Speed and Craft: Maintaining high design quality and user experience while working in a fast-paced, high-velocity environment.
• Scaling Design Systems: Contributing to and evolving a design system to support growing product lines and new features consistently.
• Remote Collaboration Nuances: Ensuring effective communication, alignment, and team cohesion in a fully remote setting.

Learning & Development Opportunities:

• AI Design Expertise: Developing specialized skills in designing for AI-powered products, staying at the forefront of this evolving field.
• Product Strategy Influence: Gaining experience in shaping product roadmaps and influencing strategic decisions.
• Cross-Product Experience: Working across different product lines (Workleap Platform and ShareGate) to broaden design expertise and market understanding.
• Mentorship and Leadership: Opportunities to mentor junior designers and take on leadership roles within design projects.
• Industry Conferences & Training: Access to professional development resources to enhance skills and knowledge.

📝 Enhancement Note: The challenges presented are inherent to a senior role in an innovative tech company. The growth opportunities are directly linked to addressing these challenges and developing expertise in areas like AI design and product strategy.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to design for a highly ambiguous problem. How did you approach it, and what was the outcome?" (Focus on your process, research, and decision-making.)
• "How do you approach designing with AI as a core material, rather than just a feature? Can you provide an example?" (Highlight your understanding of AI's potential and limitations in UX.)
• "How do you balance the need for design craftsmanship with the demand for rapid iteration in a fast-moving environment?" (Demonstrate your ability to make pragmatic decisions.)

Company & Culture Questions:

• "What interests you about Workleap's mission to make work simpler, and how does that resonate with your design philosophy?" (Show your alignment with the company's core values.)
• "Describe your ideal collaboration style within a product trio (PM, Eng, Design) in a remote setting." (Emphasize communication, feedback, and shared ownership.)
• "How do you ensure user needs are advocated for, especially when faced with business constraints or tight deadlines?" (Illustrate your user-centric approach.)

Portfolio Presentation Strategy:

• Structure Your Narrative: For each case study, clearly define the problem, your role and contributions, the process you followed, the solutions you designed, and the measurable impact.
• Show, Don't Just Tell: Use visuals (wireframes, mockups, prototypes, user flows) to illustrate your design process and final solutions.
• Quantify Results: Present key metrics that demonstrate the success of your designs. Be prepared to discuss how you gathered or interpreted these metrics.
• Emphasize AI/Ambiguity: If applicable, dedicate a section or highlight within case studies how you handled AI integration or ambiguous problem spaces.
• Be Prepared for Questions: Anticipate questions about your design choices, trade-offs, and how you would handle specific scenarios Workleap might face.

📝 Enhancement Note: Interview preparation should focus on demonstrating strategic thinking, a strong user-centered approach, proficiency in AI design, and the ability to collaborate effectively in a remote, fast-paced environment. Highlighting past successes with quantifiable results is crucial.

📌 Application Steps

To apply for this Senior Product Designer position:

• Submit your application through the Workleap careers portal via the provided link.
• Tailor Your Resume: Ensure your resume highlights your 5+ years of SaaS product design experience, specific skills in UX, UI, prototyping, and any experience with AI-adjacent features. Use keywords from the job description.
• Curate Your Portfolio: Select 3-5 strong case studies that best showcase your end-to-end design process, problem-solving skills, ability to handle ambiguity, and ideally, any experience with AI. Quantify your achievements and clearly articulate your role and impact.
• Prepare for the Interview Process: Research Workleap's products (Workleap Platform, ShareGate) and their company culture. Practice answering strategy and behavioral questions, and be ready to present your portfolio confidently.
• Understand Remote Collaboration: Be prepared to discuss how you contribute effectively in a remote-first, collaborative environment.

⚠️ 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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