Product Designer

📍 Job Overview

Job Title: Product Designer

Company: sherpa°

Location: Toronto, Ontario, Canada

Job Type: Full-Time

Category: Product Design / User Experience (UX)

Date Posted: June 01, 2026

Experience Level: 5-10 Years

Remote Status: Fully Remote (Canada)

🚀 Role Summary

• Shape the future of international travel by designing intuitive and delightful visa application experiences for millions of global travelers.

• Drive customer-centric design thinking, translating complex user needs into seamless digital and physical touchpoint solutions.

• Collaborate closely with cross-functional teams, including Product Managers, Engineers, and Customer Support, to deliver end-to-end user journeys.

• Leverage cutting-edge design tools, including Figma and AI-powered design platforms, to create high-fidelity prototypes and validate concepts.

• Take ownership of design projects from initial discovery and research through to iteration and successful product shipping.

📝 Enhancement Note: While the original job title is "Product Designer," the extensive focus on user experience, customer journey mapping, and collaboration with product managers and engineers strongly positions this role within the broader UX/Product Design spectrum, with a heavy emphasis on user-centric design principles and end-to-end product lifecycle involvement. The role requires a blend of strategic thinking and tactical execution in crafting user interfaces and experiences.

📈 Primary Responsibilities

• Design and iterate on user flows and interfaces for the visa application process, ensuring a seamless and intuitive experience for international travelers across various touchpoints.

• Conduct user research, usability testing, and concept validation in close partnership with Product Managers to gather insights and inform design decisions.

• Develop high-fidelity mockups and interactive prototypes in Figma and utilize AI design tools to effectively communicate design concepts and user journeys.

• Collaborate with engineering teams to ensure accurate implementation of designs, providing clear specifications and design system guidance.

• Contribute to the evolution of sherpa°'s design system, ensuring consistency, scalability, and adherence to best practices in usability and accessibility.

• Analyze user feedback and product performance data to identify areas for improvement and drive iterative design enhancements.

• Visualize and design for both digital interfaces and potential physical touchpoints that support the traveler's overall journey.

• Act as a champion for the user, advocating for their needs and ensuring a rewarding experience is delivered throughout the product lifecycle.

📝 Enhancement Note: The core responsibilities are heavily weighted towards the end-to-end design process, from ideation and research to prototyping, collaboration, and iteration. The emphasis on "delightful visa application experience" and "visualizing both digital and physical touchpoint solutions" suggests a holistic approach to user experience design that extends beyond traditional UI. The mention of "messy decisions" in the requirements implies a need for problem-solving in ambiguous situations.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong portfolio and proven experience in Product Design or a related field are paramount. A background in Human-Computer Interaction (HCI), Graphic Design, or a related discipline would be beneficial.

Experience: 5-8+ years of professional experience in a Product Design role, with a track record of successfully shipping complex digital products.

Required Skills:

• Product Design Expertise: Proven ability to manage the entire design lifecycle from discovery through iteration and shipping.

• Portfolio: A comprehensive portfolio showcasing a wide range of visual styles and complex product flows, demonstrating problem-solving skills and impact on shipped products.

• Figma Proficiency: Advanced skills in Figma for UI design, prototyping, and collaborative workflows.

• AI Design Tools: Familiarity and comfort with AI design tools such as Claude, Figma Make, and similar platforms for enhancing the design process.

• Prototyping: Experience in creating both traditional and AI-enhanced prototypes for desktop and mobile experiences.

• User-Centric Design: Deep understanding and application of customer-centric design thinking and user research methodologies.

• Usability & Accessibility: Keen eye for usability best practices and strong commitment to designing accessible interfaces.

• Communication & Presentation: Clear, compelling presentation and communication skills, with the ability to articulate design decisions and rationale effectively.

• Ownership & Drive: A proactive and self-motivated individual who takes ownership of ensuring a rewarding user experience.

Preferred Skills:

• Design Systems: Demonstrated understanding of basic design system principles and practices.

• Cross-functional Collaboration: Experience working effectively within cross-functional teams (Product, Engineering, Customer Support).

• Visual Design Range: Ability to demonstrate visual range across brand and product, not just "tidy-but-flat" work.

• Handling Ambiguity: Comfort and proficiency in dealing with ambiguous requirements that necessitate creative investigation.

📝 Enhancement Note: The "5-8+ years" experience level, combined with the emphasis on shipping "complex flows" and handling "messy decisions," suggests this role is for a mid to senior-level Product Designer. The requirement for a portfolio that proves "real visual range" and the ability to "walk through the messy decisions" indicates a preference for designers who can demonstrate strategic thinking and problem-solving beyond aesthetics.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Case Studies: Present one or more detailed case studies that clearly showcase your impact on the product, focusing on the problem, your process, the solutions you devised, and the measurable outcomes.

• Process Demonstration: Walk through the "messy decisions" and trade-offs made during the design process, not just the polished final result, to illustrate problem-solving capabilities.

• Visual Range: Showcase a diverse portfolio demonstrating visual range across different brand aesthetics and product types, highlighting adaptability and creative breadth.

• User Journey Visualization: Include examples of how you've visualized and designed for end-to-end user journeys, encompassing both digital interfaces and any relevant physical touchpoints.

Process Documentation:

• Design Lifecycle: Clearly document your involvement across various stages of the design lifecycle, from ideation and research to prototyping, validation, and iterative design.

• Concept Validation: Demonstrate how you've partnered with Product Managers to rapidly validate concepts prior to development, including any methods used for testing and feedback.

• System Integration: Show examples of how your designs integrate with existing systems or contribute to the development/maintenance of design systems.

📝 Enhancement Note: The emphasis on "messy decisions," "shipped complex flows," and "impact on the product" strongly suggests that the portfolio review will be a critical component of the interview process. Candidates should prepare to deep-dive into their case studies, articulating the strategic thinking, problem-solving, and iterative processes that led to successful product outcomes. The mention of "visualizing both digital and physical touchpoint solutions" implies a need to showcase a holistic understanding of the user's entire journey.

💵 Compensation & Benefits

Salary Range: CAD $100,000 - $150,000 per year. This range is based on the provided salary data and is typical for a Product Designer with 5-10 years of experience in a major Canadian tech hub like Toronto, considering the company's high-growth startup status and equity offerings.

Benefits:

• Competitive Base Salary: A strong base salary reflecting experience and market value.

• Comprehensive Benefits: Health, dental, and vision coverage, providing robust support for employee well-being.

• Early-Stage Stock Options: Opportunity for significant financial upside through equity participation in a high-growth startup.

• Generous Vacation Policy: Initially 4 weeks of vacation, with a move towards an unlimited vacation plan, promoting work-life balance.

• Learning and Development Fund: Dedicated budget to support continuous learning, skill development, and professional growth.

• Flexibility: Options to work from home or from the Toronto office, catering to individual preferences and needs.

Working Hours: Approximately 40 hours per week, with flexibility offered through remote work options and a progressive vacation policy.

📝 Enhancement Note: The provided salary range of $100,000 - $150,000 CAD for a Product Designer with 5-10 years of experience in Toronto is well-aligned with industry benchmarks for this role and location. The inclusion of early-stage stock options is a significant component of the total compensation for a high-growth startup, offering potential for substantial financial reward beyond the base salary. The "moving towards unlimited vacation plan" indicates a company culture that values employee well-being and autonomy.

🎯 Team & Company Context

🏢 Company Culture

Industry: Travel Technology (Travel Tech) - sherpa° operates within a dynamic and rapidly evolving sector, focused on simplifying international travel by providing accurate travel documentation information and enhancing border crossing experiences. This industry often requires agility, data-driven decision-making, and a strong focus on user experience due to the global and diverse user base.

Company Size: High-growth tech startup. This implies a fast-paced environment where individual contributions have a significant impact. Operations professionals will likely experience a dynamic workflow, opportunities to shape processes, and direct collaboration with leadership.

Founded: The company was founded prior to 2026 (exact year not specified). As a high-growth startup, it suggests a period of active scaling and product development, with established foundational processes but still room for optimization.

Team Structure:

• Cross-functional Teams: Product Designers work within cross-functional teams, collaborating closely with Product Managers, Engineers, and Customer Support. This structure fosters a holistic approach to product development.

• Collaborative Environment: The company emphasizes a positive working environment with regular team events and social activities, suggesting a culture that values teamwork and interpersonal relationships.

• Ownership Culture: Team members are encouraged to take ownership of their work, indicating a culture of accountability and empowerment.

Methodology:

• Customer-Centric Design: A core methodology is designing with the traveler's needs at the forefront, focusing on creating "delightful" experiences.

• Data-Driven Iteration: Product improvements are informed by user feedback and product performance data, emphasizing an iterative design approach.

• Agile Development: The nature of a high-growth startup and cross-functional teams suggests an agile or agile-like development methodology, allowing for rapid validation and iteration.

Company Website: https://joinsherpa.com

📝 Enhancement Note: As a high-growth startup in the Travel Tech space, sherpa° likely values innovation, adaptability, and a strong user focus. The emphasis on "helping travellers move freely around the world" and "shifting the way the world's leading travel providers think about borders" points to an ambitious mission. The company culture appears to be supportive and team-oriented, with opportunities for significant individual impact.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned as a mid-to-senior level Product Designer (5-8+ years of experience). It requires the ability to independently manage complex design projects from conception to completion, demonstrating strategic thinking and ownership. The impact is significant, with work seen by millions of travelers globally.

Reporting Structure: The Product Designer will work closely with Product Managers and within cross-functional teams. While direct reporting lines aren't specified, it's typical for designers in such structures to report to a Design Lead, Head of Product, or Product Manager, depending on the team's organization.

Operations Impact: The designer's work directly influences the user experience of millions of travelers across 193 countries, impacting critical journeys like visa applications. This role has a direct impact on customer satisfaction, product adoption, and potentially revenue through simplified and trustworthy travel processes.

Growth Opportunities:

• Skill Specialization: Opportunity to deepen expertise in specific areas of UX/Product Design, such as complex flow design, AI-assisted design, or user research methodologies.

• Leadership Potential: As the company grows, there may be opportunities to mentor junior designers, lead design initiatives, or move into more senior or management roles within the design or product teams.

• Product Influence: Direct contribution to shaping a product used by a global audience, providing high visibility and significant portfolio-building experience.

• Learning & Development: Access to a dedicated learning and development fund allows for continuous skill enhancement through courses, conferences, or certifications relevant to product design and the travel tech industry.

📝 Enhancement Note: The role offers substantial growth potential due to the company's high-growth startup nature. Designers can expect to gain experience in tackling complex, large-scale UX challenges within a dynamic environment. The opportunity to influence product direction and potentially take on leadership responsibilities makes this an attractive position for career advancement in the product design field.

🌐 Work Environment

Office Type: The company offers flexibility with options to work from home or from their Toronto office. This hybrid or remote-first approach caters to diverse working preferences.

Office Location(s): Toronto, Ontario, Canada. This location is a major tech hub, offering access to a vibrant ecosystem of talent and innovation.

Workspace Context:

• Collaborative Spaces: Whether working remotely or in the office, the environment encourages close collaboration with product managers, engineers, and customer support through digital tools and potential in-person interactions.

• Tools & Technology: Access to industry-standard design tools like Figma and emerging AI design tools is provided, ensuring designers have the necessary resources for their work.

• Global Reach: The opportunity to work on a product used by millions of travelers worldwide provides a unique and motivating context for the workspace.

Work Schedule: While a standard 40-hour work week is implied, the remote flexibility and progressive vacation policy suggest a culture that prioritizes output and work-life balance over strict adherence to traditional office hours.

📝 Enhancement Note: The emphasis on remote work flexibility, combined with the vibrant tech hub location of Toronto, suggests a modern and adaptable work environment. This setup is conducive to deep work and focused design tasks, while still facilitating necessary team collaboration.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Review of resume and portfolio to assess experience, skills, and alignment with role requirements.

• Portfolio Presentation: A dedicated session to present case studies from your portfolio, detailing your design process, problem-solving approach, and the impact of your work. Be prepared to discuss "messy decisions" and trade-offs.

• Cross-functional Interviews: Discussions with Product Managers, Engineers, and potentially other stakeholders to assess collaboration style, technical understanding, and cultural fit.

• Design Challenge (Potential): You might be asked to complete a small design exercise or critique an existing product, focusing on your thought process and methodology.

• Final Interview: Likely with senior leadership to discuss overall fit, strategic thinking, and alignment with the company's mission.

Portfolio Review Tips:

• Show, Don't Just Tell: Use your case studies to illustrate your skills. Focus on the why and how behind your design choices.

• Emphasize Impact: Quantify your impact whenever possible (e.g., improved conversion rates, reduced support tickets, increased user satisfaction scores).

• Detail the Process: Clearly articulate the problem, your research methods, design iterations, user testing feedback, and how you arrived at the final solution. Be ready to discuss challenges and how you overcame them.

• Highlight Visual Range: Ensure your portfolio showcases diverse styles and solutions, demonstrating adaptability and a broad design sensibility.

• Prepare for Ambiguity: Given the job description, be ready to discuss how you approach ambiguous problems and requirements.

Challenge Preparation:

• Understand the User: For any design challenge, prioritize understanding the user and their context.

• Think Holistically: Consider the entire user journey, including potential physical touchpoints if applicable.

• Articulate Your Reasoning: Clearly explain your thought process, design decisions, and any assumptions made.

• Focus on Process: Even if time is limited, demonstrating a structured problem-solving approach is key.

📝 Enhancement Note: The interview process will likely heavily scrutinize the candidate's portfolio and their ability to articulate complex design decisions and their impact. Candidates should prepare to discuss their contributions to shipped products, especially those involving complex flows and handling ambiguity. The emphasis on "customer-centric design thinking" and "visualizing both digital and physical touchpoint solutions" means interviewers will look for a holistic approach to user experience.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: The primary tool for UI design, prototyping, and collaborative workflows. Proficiency is essential.

• AI Design Tools: Claude, Figma Make, and similar AI-powered tools for enhancing design efficiency, ideation, and prototyping. Familiarity is expected.

Analytics & Reporting:

• While not explicitly listed, experience with product analytics tools (e.g., Amplitude, Mixpanel, Google Analytics) would be beneficial for understanding user behavior and informing design decisions.

• Familiarity with data visualization tools could also be advantageous for presenting design impact. CRM & Automation:

• Not directly relevant to the Product Designer role, but understanding how designs integrate into broader product ecosystems and user management systems (potentially involving CRM data) is helpful.

📝 Enhancement Note: The explicit mention of Figma and AI design tools (Claude, Figma Make) highlights the company's commitment to modern design workflows. Candidates should be prepared to discuss their experience with these specific tools and their application in creating seamless user experiences.

👥 Team Culture & Values

Operations Values:

• Customer Focus: A paramount value, evident in the mission to help travelers and the focus on creating "delightful" experiences. Decisions are driven by user needs and journey optimization.

• Ownership & Accountability: Team members are expected to take initiative and own their work, contributing directly to the company's growth and success.

• Collaboration: The emphasis on cross-functional teams and regular social activities points to a culture that values teamwork and open communication.

• Innovation & Agility: As a high-growth startup in the tech sector, a culture of continuous innovation and the ability to adapt quickly to changing market needs and user feedback is likely highly valued.

• Personal Growth: The company explicitly mentions a commitment to personal growth and provides a learning and development fund, indicating a value placed on continuous improvement and skill development.

Collaboration Style:

• Cross-functional Integration: Designers are embedded in teams with Product Managers and Engineers, fostering tight collaboration and a shared understanding of product goals.

• Open Communication: Regular team events and social activities suggest an environment that encourages open dialogue and strong working relationships.

• Iterative Feedback: The design process involves rapid validation and iteration, implying a culture where feedback is actively sought and incorporated.

📝 Enhancement Note: The company culture appears to be a blend of startup dynamism with a strong emphasis on user advocacy and collaborative problem-solving. Values like ownership, customer-centricity, and continuous learning are likely to be key drivers of success within the team.

⚡ Challenges & Growth Opportunities

Challenges:

• Designing for Global Complexity: Creating a "delightful" visa application experience that caters to travelers from 193 countries, each with unique requirements and cultural nuances, presents a significant design challenge.

• Balancing Ambiguity with Structure: The role requires comfort with ambiguous requirements while needing to deliver clear, structured, and user-friendly solutions.

• Rapid Iteration in a High-Growth Environment: Keeping pace with rapid product development cycles and evolving business needs requires adaptability and efficient design processes.

• Visualizing End-to-End Journeys: Effectively designing for both digital interfaces and potential physical touchpoints within the traveler's journey requires a comprehensive and integrated approach.

Learning & Development Opportunities:

• Advanced UX/Product Design: Opportunity to hone skills in complex problem-solving, user research, and end-to-end product design within a high-impact context.

• AI Design Tool Exploration: Hands-on experience with cutting-edge AI design tools, contributing to the future of design practices.

• Global Product Exposure: Working on a product used by millions worldwide provides invaluable experience in designing for diverse international markets.

• Startup Growth Experience: Gaining experience in a fast-paced, high-growth startup environment offers unique career development opportunities and insights into building successful tech companies.

📝 Enhancement Note: The challenges presented are directly tied to the nature of the product and the company's stage. Overcoming them will require strong problem-solving skills, adaptability, and a deep understanding of user needs on a global scale. The growth opportunities are substantial, offering a chance to develop expertise in a niche but critical area of travel technology development.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to design for a complex, ambiguous problem. How did you approach it, and what was the outcome?" (Focus on your process, problem decomposition, and iterative solutions.)

• "How do you ensure your designs are truly customer-centric, especially when dealing with potentially sensitive or complex processes like visa applications?" (Discuss user research, empathy mapping, and validation techniques.)

• "Walk us through a complex flow you designed from discovery to shipping. What were the biggest challenges, and how did you overcome them? What was the measurable impact?" (Be prepared to discuss trade-offs and "messy decisions.") Company & Culture Questions:

• "Why are you interested in sherpa° and our mission to simplify international travel?" (Research the company's mission, values, and recent news.)

• "How do you approach collaboration within a cross-functional team (Product Managers, Engineers)?" (Highlight your communication style and experience working with diverse stakeholders.)

• "How do you stay updated with the latest design trends and technologies, particularly in areas like AI design?" (Showcase your commitment to continuous learning.) Portfolio Presentation Strategy:

• Structure Your Case Studies: For each case study, clearly define the problem, your role, the process (research, ideation, design, testing), the solution, and the impact/outcomes.

• Showcase Your Process: Emphasize your thought process, the rationale behind your decisions, and how you handled challenges and feedback. Be ready to discuss the "messy decisions."

• Quantify Impact: Wherever possible, use data and metrics to demonstrate the success of your designs.

• Visual Clarity: Ensure your presentation is visually appealing and easy to follow. Use high-quality mockups and prototypes.

• Practice Delivery: Rehearse your presentation to ensure you can articulate your points concisely and confidently within the allotted time.

📝 Enhancement Note: Interview preparation should focus on demonstrating a deep understanding of the end-to-end design process, a strong user-centric mindset, and the ability to articulate complex problem-solving strategies. Candidates should be ready to discuss their experience with Figma and AI design tools, and how they've handled ambiguity and iterated on designs based on user feedback and business needs.

📌 Application Steps

To apply for this Product Designer position:

• Submit your application through the provided link on Ashby.

• Portfolio Customization: Tailor your resume and portfolio to highlight your experience with complex digital flows, customer-centric design, and your proficiency with Figma and AI design tools. Showcase case studies that demonstrate your problem-solving process and measurable impact.

• Resume Optimization: Ensure your resume clearly outlines your 5-8+ years of product design experience, emphasizing achievements related to user experience, UI design, prototyping, and cross-functional collaboration. Use keywords from the job description.

• Interview Preparation: Practice articulating your design process, especially how you handle ambiguity and make "messy decisions." Prepare to present your portfolio case studies in detail, focusing on impact and collaboration.

• Company Research: Familiarize yourself with sherpa°'s mission, product, and the broader travel technology landscape. Understand how your design skills can contribute to their goal of simplifying international travel.

⚠️ 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.