Senior Product Designer - ShareGate Migrate

📍 Job Overview

Job Title: Senior Product Designer - ShareGate Migrate

Company: ShareGate (Workleap Technologies)

Location: Canada - Remote

Job Type: Full-Time

Category: Product Design / User Experience

Date Posted: March 31, 2026

Experience Level: 6+ Years

Remote Status: Fully Remote

🚀 Role Summary

• Lead end-to-end product design for the ShareGate Migrate platform, focusing on simplifying complex IT migration workflows.

• Transform ambiguous technical challenges into intuitive and effective user experiences for IT professionals and administrators.

• Collaborate closely within a product trio (PM, Tech Lead, Designer) to shape product strategy and execution.

• Drive innovation by exploring and integrating AI-powered features to enhance migration planning, insights, and technical guidance.

• Contribute to the evolution of the company's design system and ensure a consistent, high-quality user experience across products.

📝 Enhancement Note: This role is positioned within a specialized product team, "ShareGate Migrate," indicating a focus on a specific, operationally critical segment of the company's offerings. The emphasis on "IT professionals" and "complex migration scenarios" signals a need for deep understanding of B2B SaaS, technical audiences, and the intricacies of data migration and governance. The explicit mention of AI integration suggests a forward-thinking approach to product development, requiring designers to be adept at exploring and incorporating emerging technologies.

📈 Primary Responsibilities

• Lead the complete design lifecycle for the ShareGate Migrate product, from problem definition and strategic planning to detailed interaction design and UI refinement.

• Translate complex, technical workflows related to Microsoft 365 and cloud migrations into clear, actionable, and user-friendly experiences.

• Develop wireframes, user flows, prototypes, and high-fidelity designs that effectively address the needs of IT administrators and technical users.

• Foster strong collaborative relationships with Product Managers, Tech Leads, engineers, and subject matter experts to ensure strategic alignment and technical feasibility.

• Conduct user research, usability testing, and data analysis (customer feedback, usage patterns) to inform design decisions and drive product improvements.

• Actively explore and propose AI-driven features that can simplify migration processes, provide predictive insights, and guide users through complex technical decisions.

• Contribute to the advancement of the design team's processes, methodologies, and tooling, including the adoption of new innovation techniques.

• Maintain and evolve the company's design system to ensure consistency, scalability, and accessibility across the ShareGate product suite.

• Prototype iteratively using various tools, including AI-powered prototyping solutions, to communicate concepts, validate assumptions, and expedite the design process.

• Craft compelling narratives and articulate design rationale to stakeholders, effectively influencing product direction and engineering execution.

📝 Enhancement Note: The responsibilities highlight a "T-shaped" designer profile: deep expertise in end-to-end design (the vertical bar) combined with broad collaboration and strategic input across product planning and AI exploration (the horizontal bar). The emphasis on "simplifying Microsoft 365 and cloud-migration scenarios" and "technical audiences" strongly suggests a need for experience in enterprise software and infrastructure management domains.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong portfolio demonstrating equivalent practical experience and a deep understanding of UX principles is essential.

Experience: Minimum of 6 years of dedicated experience in Product Design, specifically within the B2B SaaS domain, with a proven track record of delivering impactful user experiences.

Required Skills:

• End-to-End Product Design: Demonstrated ability to manage the entire design process from conceptualization to final implementation.

• User Experience (UX) Design: Strong user-centric approach with a deep understanding of user research, journey mapping, and information architecture.

• UI Design: Proficiency in creating clean, intuitive, and aesthetically pleasing user interfaces that adhere to design system standards.

• Prototyping: Expertise in creating interactive prototypes at various fidelities using industry-standard tools (e.g., Figma, Sketch, Adobe XD) and a willingness to explore AI-assisted prototyping.

• Technical Problem Solving: Confidence and capability in navigating and simplifying ambiguous, technically complex problem spaces relevant to IT administration and data migration.

• Collaboration & Communication: Excellent verbal and written communication skills, with a proven ability to collaborate effectively with cross-functional teams (Product Management, Engineering) and present design solutions persuasively.

• Data-Driven Decision Making: Ability to leverage user feedback, analytics, and customer insights to inform design strategies and measure outcomes.

• Design Systems: Experience in contributing to, or working within, established design systems to ensure product consistency and scalability.

• Attention to Detail: A meticulous approach to craft, ensuring high quality in all aspects of design output.

Preferred Skills:

• B2B SaaS Product Design: Specific experience designing for enterprise software, particularly in areas like IT administration, data management, or infrastructure tools.

• AI-Powered Experience Design: Previous experience designing or contributing to AI-integrated features or products.

• Storytelling: Strong narrative skills to articulate design rationale and project impact to various stakeholders.

• Agile Methodologies: Familiarity with agile development processes and the ability to work effectively within fast-paced, iterative cycles.

• Microsoft 365 Ecosystem Knowledge: Understanding of Microsoft 365 environments, SharePoint, Exchange, and related cloud technologies is highly advantageous.

📝 Enhancement Note: The "6+ years" requirement, combined with the emphasis on "B2B SaaS," "technical audiences," and "complex problem spaces," suggests this role is for a seasoned designer capable of strategic thinking and independent execution. The preference for AI and Microsoft 365 experience points towards a need for specialized knowledge relevant to the product's domain.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Case Studies: Showcase 3-5 comprehensive case studies demonstrating end-to-end product design ownership for B2B SaaS products.

• Problem Framing: Clearly articulate the problem space, user needs, and business objectives for each case study.

• Process Documentation: Detail your design process, including user research, ideation, wireframing, prototyping, user testing, and iteration.

• UI/UX Deliverables: Include high-fidelity mockups, interactive prototypes, and examples of UI elements and interaction design.

• Impact & Outcomes: Quantify the impact of your design solutions with metrics (e.g., conversion rates, task completion times, user satisfaction scores, efficiency gains).

• Technical Audience Focus: Highlight projects specifically designed for technical users or complex workflows.

• AI Integration Examples: If available, include examples of designing with or for AI-powered features.

Process Documentation:

• Workflow Optimization: Demonstrate how you've analyzed and improved existing technical workflows through design.

• System Integration: Illustrate how your designs consider and integrate with broader software ecosystems or design systems.

• Iterative Design: Showcase examples of iterative design based on feedback, data, or evolving requirements.

• AI Exploration Documentation: If applicable, detail your approach to exploring and prototyping AI-driven functionalities.

📝 Enhancement Note: For a Senior Product Designer role, particularly in a technically complex domain like migration software, the portfolio is paramount. It needs to go beyond visual design to demonstrate strategic thinking, problem-solving capabilities, and a deep understanding of user workflows within enterprise IT environments. Emphasis should be placed on quantifiable results and the ability to translate complex technical requirements into user-friendly solutions.

💵 Compensation & Benefits

Salary Range: $120,000 - $145,000 CAD per year. This range is based on the provided information and reflects the company's Canada-wide compensation scale. The final offer may be adjusted based on the candidate's specific region within Canada to align with local market conditions and cost of living.

Benefits:

• Comprehensive Health Coverage: Includes medical, dental, and vision insurance plans.

• Retirement Savings Plan: Contributions or matching programs for long-term financial security.

• Generous Paid Time Off: Vacation days, sick leave, and public holidays, designed to promote work-life balance.

• Professional Development: Budget or opportunities for continued learning, conferences, workshops, and skill enhancement relevant to design and AI.

• Remote Work Support: Stipend or reimbursement for home office setup and internet connectivity.

• Employee Wellness Programs: Initiatives focused on mental health, physical well-being, and work-life integration.

• Stock Options/Equity: Potential for participation in company growth through equity programs.

Working Hours: Standard full-time hours, typically around 40 hours per week. The company emphasizes autonomy and ownership, suggesting flexibility in daily scheduling as long as responsibilities are met and collaboration with teams across different time zones is managed effectively.

📝 Enhancement Note: The salary range is provided explicitly, with a note on regional adjustment. This is crucial for candidates in Canada. The benefits list is inferred from typical offerings for senior tech roles, emphasizing aspects relevant to remote work and professional growth. The working hours are standard but with an emphasis on flexibility.

🎯 Team & Company Context

🏢 Company Culture

Industry: Software Development, specifically focusing on Microsoft 365 migration, governance, and IT management solutions.

Company Size: Part of Workleap Technologies, a growing software company with a significant employee base (likely 500+ employees based on typical tech company structures). This size suggests a balance between established processes and the agility of a growth-stage company.

Founded: Workleap Technologies was founded in 2006. ShareGate has been a key product developed since then, establishing a long history and deep expertise in its niche.

Team Structure:

• Product Trio Model: The designer will work within a close-knit product trio comprising a Product Manager, a Tech Lead, and the Senior Product Designer. This structure promotes tight collaboration and shared ownership.

• Design Team: Designers are integrated early in the product development process and are part of a collaborative, feedback-rich design community within Workleap.

• Cross-Functional Collaboration: Expect close partnerships with engineering teams, QA, marketing, and customer success to ensure a cohesive product experience and market fit.

Methodology:

• Agile Development: The company likely employs agile methodologies, emphasizing iterative development, rapid learning, and continuous improvement.

• Data-Informed Design: Decisions are guided by a combination of user research, customer feedback, product analytics, and market trends.

• AI Exploration: A proactive approach to integrating AI to enhance product functionality and user experience.

• Design System Governance: Commitment to maintaining and evolving a robust design system for consistency and efficiency.

Company Website: https://sharegate.com/ and https://www.workleap.com/

📝 Enhancement Note: The company culture is described as driven by curiosity, bold building, and a desire to simplify work. They emphasize experimentation, rapid learning, and embracing discomfort for growth. This suggests a dynamic, challenging, yet supportive environment. The "Trio" model is a key indicator of how product teams operate, ensuring designers are integral to strategic decisions.

📈 Career & Growth Analysis

Operations Career Level: This is a Senior-level Product Designer role. It implies a high degree of autonomy, ownership, and the ability to influence product strategy and execution. The role requires not just design craft but also strong collaboration and strategic thinking.

Reporting Structure: The Senior Product Designer will likely report to a Design Lead or Head of Design within Workleap Technologies, while working day-to-day within their dedicated "ShareGate Migrate" product trio.

Operations Impact: The role has a direct and significant impact on the usability and effectiveness of the ShareGate Migrate product, which is critical for organizations undertaking Microsoft 365 migrations. Successful design contributes to customer satisfaction, adoption rates, and revenue by making complex IT operations simpler and more reliable. The focus on AI integration also positions the role at the forefront of future product evolution.

Growth Opportunities:

• Leadership within Design: Potential to mentor junior designers, lead design initiatives, or take on more strategic product design responsibilities.

• Specialization: Deepen expertise in B2B SaaS, complex technical product design, or AI-driven user experiences.

• Cross-Product Influence: Contribute to the broader design system and product ecosystem of Workleap Technologies.

• Skill Development: Opportunities to learn and apply new design tools, methodologies, and AI technologies through company-provided resources or industry engagement.

• Career Path: Progression could lead to Principal Product Designer, Design Lead, or Product Management roles, depending on individual aspirations and performance.

📝 Enhancement Note: The "Senior" title coupled with the "product trio" model and "end-to-end" responsibility strongly suggests this is a high-impact, strategic role. Growth opportunities are framed around both design leadership and specialized technical/strategic development, common in thriving SaaS companies.

🌐 Work Environment

Office Type: Fully Remote. This indicates a distributed workforce, with no requirement for in-office presence.

Office Location(s): While the role is remote within Canada, Workleap Technologies is headquartered in Montréal. The company operates a distributed model with employees across Canada.

Workspace Context:

• Home Office Environment: Candidates are expected to have a dedicated, productive workspace at home.

• Digital Collaboration Tools: Reliance on tools like Microsoft Teams, Slack, and collaborative design platforms (Figma, Miro) for communication and teamwork.

• Asynchronous & Synchronous Communication: The remote nature necessitates proficiency in both real-time collaboration and effective asynchronous communication to bridge time zones and work styles.

• Access to Technology: Engineers and designers will have access to modern software development and design tools, including AI prototyping tools.

Work Schedule: Flexible, but with a strong emphasis on communication and collaboration across time zones. Expect core working hours to overlap with colleagues in Canada to facilitate team meetings, design critiques, and cross-functional syncs. The company culture values thoughtfulness and continuous learning, implying a supportive environment for focused work.

📝 Enhancement Note: The fully remote nature is a key characteristic. The emphasis on "Canada-Remote" suggests that while the company is Canadian, candidates must be located within Canada for compensation and legal purposes. The work environment is digitally driven, requiring strong self-management and communication skills.

📄 Application & Portfolio Review Process

Interview Process:

• Phone Screen: Initial conversation to assess basic qualifications, experience, and cultural fit.

• Virtual Interview (Microsoft Teams): In-depth discussion with the hiring team (likely PM, Tech Lead, and possibly another designer). This stage will focus on experience, problem-solving approaches, and design philosophy.

• Work Sample/Design Challenge: A practical exercise designed to evaluate your design process, problem-solving skills, and ability to translate technical requirements into design solutions. This might involve a take-home assignment or a live design critique.

• Job Offer: Final stage extending an employment offer.

Portfolio Review Tips:

• Curate for Relevance: Select case studies that best represent your experience with complex B2B SaaS products, technical audiences, and end-to-end design ownership.

• Highlight the "Why" and "How": Clearly articulate the problem, your strategic approach, your design process, and the rationale behind your decisions for each project.

• Showcase Impact: Quantify the results and business impact of your design work using metrics.

• Demonstrate AI Exploration: If you have relevant experience, showcase how you've explored or designed AI-powered features.

• Prepare to Discuss: Be ready to walk through your portfolio, discuss your contributions, and answer questions about your process and decision-making.

Challenge Preparation:

• Understand the Domain: Familiarize yourself with ShareGate's product, the challenges of Microsoft 365 migration, and the needs of IT administrators.

• Focus on Process: Demonstrate a structured design process, even under time constraints.

• Think Aloud: For live challenges, articulate your thought process clearly.

• Ask Clarifying Questions: Don't hesitate to seek more information to ensure you're addressing the core problem.

• Consider AI Integration: If the challenge allows, think about how AI could enhance the solution.

📝 Enhancement Note: The interview process is standard for senior design roles, with a strong emphasis on a practical work sample. The portfolio review is critical, and candidates should prepare to showcase their strategic thinking and impact, not just visual output. Understanding the specific domain (IT migration) will be a significant advantage.

🛠 Tools & Technology Stack

Primary Design Tools:

• Figma: Likely the primary tool for UI design, prototyping, and collaboration, given its industry prevalence.

• Sketch / Adobe XD: May be used, but Figma is more probable for a modern SaaS company.

• Prototyping Tools: Figma's built-in prototyping, potentially supplemented by specialized tools or AI-assisted prototyping solutions mentioned in the job description.

• Collaboration Tools: Miro, Mural for whiteboarding, brainstorming, and user flow mapping.

Analytics & Reporting:

• Product Analytics Platforms: Tools like Amplitude, Mixpanel, or Pendo for understanding user behavior and in-product analytics.

• Customer Feedback Tools: Platforms for collecting and analyzing user feedback (e.g., UserVoice, Canny, surveys).

CRM & Automation:

• CRM Software: Potentially Salesforce or Dynamics 365, though direct interaction may be limited for a designer.

• Project Management Tools: Jira, Asana, or Trello for tracking tasks, sprints, and project progress.

AI Tools:

• AI Prototyping Tools: As mentioned, the company is exploring these, so familiarity or a willingness to learn would be beneficial.

• AI for Research/Analysis: Potentially using AI tools to assist in analyzing customer feedback or market trends.

📝 Enhancement Note: The toolset reflects a modern B2B SaaS design environment. Proficiency in Figma and collaborative tools is almost certainly a requirement. The mention of AI prototyping tools is a key differentiator, signaling a need for designers to be adaptable and forward-thinking.

👥 Team Culture & Values

Operations Values:

• Curiosity & Boldness: Encouragement to explore new ideas and tackle challenging problems proactively.

• Simplicity: A core value for the ShareGate product, aiming to make complex tasks easy for users.

• Experimentation & Learning: Embracing trial and error, rapid learning, and growth through challenges.

• Customer-Centricity: Keeping users at the center of all product development decisions.

• Collaboration & Trust: Working together, supporting each other, and building strong team relationships.

• Ownership & Accountability: Taking responsibility for one's work and its impact.

Collaboration Style:

• Product Trio Synergy: Close, integrated work within small product teams.

• Feedback-Rich Environment: Regular design critiques and open communication channels for constructive feedback.

• Cross-Functional Partnership: Strong working relationships with engineering and product management, characterized by mutual respect and shared goals.

• Inclusivity: A commitment to creating a healthy and inclusive work environment for everyone.

📝 Enhancement Note: The company's values are clearly articulated and emphasize a proactive, learning-oriented, and collaborative culture. These are critical for a remote, senior-level role where self-motivation and effective teamwork are paramount.

⚡ Challenges & Growth Opportunities

Challenges:

• Complexity of Technical Workflows: Designing intuitive solutions for intricate IT migration processes requires deep empathy and analytical skill.

• Balancing Speed and Quality: Delivering high-quality, polished designs within agile development cycles can be demanding.

• Integrating AI Effectively: Exploring and implementing AI features in a way that genuinely enhances user experience without adding complexity.

• Maintaining Design System Scalability: Ensuring the design system supports evolving product needs and new patterns across multiple products.

• Remote Collaboration: Effectively building rapport and maintaining strong collaborative ties in a fully remote setting.

Learning & Development Opportunities:

• AI Design Exploration: Opportunity to be at the forefront of integrating AI into enterprise software design.

• Deep Domain Expertise: Developing specialized knowledge in Microsoft 365 migrations and IT governance.

• Design System Leadership: Contributing to the growth and governance of a scalable design system.

• Cross-Functional Acumen: Enhancing strategic influence by working closely with product management and engineering leadership.

• Industry Engagement: Potential for attending conferences, workshops, and participating in the broader design community.

📝 Enhancement Note: The challenges are directly tied to the nature of the product and the company’s forward-looking approach (AI). Growth opportunities are framed around specialization, leadership, and leveraging cutting-edge technologies, aligning with a senior-level career trajectory.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to design for a technically complex workflow. How did you approach it, and what was the outcome?" (Focus on your process, user research, and problem-solving.)

• "How would you approach designing an AI-powered feature to help IT administrators anticipate migration risks?" (Demonstrate your thinking on AI integration, user needs, and potential challenges.)

Company & Culture Questions:

• "What interests you about ShareGate and its mission to simplify Microsoft 365 migrations?" (Show you've researched the company and product.)

• "How do you foster collaboration and provide constructive feedback within a remote, cross-functional team?" (Address your remote work style and team contributions.)

Portfolio Presentation Strategy:

• Structure is Key: Organize your presentation logically, starting with the problem, your process, your solutions, and the impact.

• Tell a Story: Frame each case study as a narrative with a clear beginning, middle, and end.

• Quantify Everything Possible: Use metrics to demonstrate the value and success of your designs.

• Be Prepared to Dive Deep: Anticipate questions about your specific contributions, design choices, and challenges faced.

• Showcase AI Thought Process: If you have AI-related projects, explain your approach to ideation, prototyping, and user feedback for those specific features.

📝 Enhancement Note: Interview preparation should focus on demonstrating strategic thinking, a robust design process, and the ability to navigate complex technical domains. The emphasis on AI and B2B SaaS means candidates should be ready to discuss these aspects in detail.

📌 Application Steps

To apply for this Senior Product Designer position:

• Submit your application through the provided link on the Greenhouse job board.

• Portfolio Customization: Tailor your resume and portfolio to highlight your experience with B2B SaaS, complex technical products, end-to-end design, and any AI-related projects. Ensure your portfolio showcases relevant case studies with clear problem statements, process documentation, and quantifiable impact.

• Resume Optimization: Use keywords from the job description, such as "Product Design," "B2B SaaS," "IT Administration," "AI," "Prototyping," and "User Experience." Clearly articulate your years of experience and specific accomplishments.

• Prepare for the Process: Familiarize yourself with the interview stages outlined (phone screen, virtual interview, work sample). Practice discussing your portfolio and design process, and research ShareGate and Workleap Technologies thoroughly.

• Research the Domain: Gain a basic understanding of Microsoft 365 migration challenges and the role of IT administrators to better contextualize your experience and approach during interviews.

⚠️ 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.