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 / UX/UI
Date Posted: 2025-12-15
Experience Level: 6+ Years
Remote Status: Fully Remote (Canada)

🚀 Role Summary

• Lead the end-to-end design process for the ShareGate Migrate product, focusing on complex, operationally sensitive migration and governance scenarios for Microsoft 365.
• Translate ambiguous and technically intricate workflows into intuitive, purposeful user experiences tailored for IT professionals and administrators.
• Drive product strategy and execution by collaborating closely within a product trio (Product Manager, Tech Lead, Designer) to define problem spaces, shape user flows, and refine UI details.
• Explore and integrate AI-driven opportunities to enhance user experience, simplify planning, surface insights, and guide technical decision-making within migration and governance processes.
• Contribute to the evolution of a robust design system, ensuring consistency and scalability across the ShareGate product suite and new feature development.

📝 Enhancement Note: The role is positioned as a Senior Product Designer within a specific product line ("ShareGate Migrate"), emphasizing its strategic importance and the need for deep collaboration with Product Management and Engineering. The focus on "operationally sensitive projects" and "IT administrators" indicates a B2B SaaS context demanding clarity, reliability, and a strong understanding of technical workflows. The explicit mention of AI integration highlights a forward-looking approach to product development.

📈 Primary Responsibilities

• Spearhead the entire design lifecycle for assigned features and product areas, from initial problem framing and user research to the final pixel-perfect UI and interaction details.
• Conceptualize and design intuitive user flows, wireframes, and interactive prototypes that simplify complex Microsoft 365 migration, tenant-to-tenant migration, and cloud governance scenarios.
• Collaborate intimately with Product Managers to define product strategy, clarify scope, and identify opportunities for user-centric innovation.
• Partner closely with Engineering teams to ensure design feasibility, uphold quality standards, and facilitate seamless implementation of designs.
• Conduct user research, usability testing, and data analysis (customer feedback, product insights, support trends) to inform design decisions and iterate on solutions.
• Proactively identify and design AI-powered features that enhance efficiency, predictability, and reliability in migration planning, execution, and governance.
• Contribute to the continuous improvement of the design workflow by introducing new tools, methodologies, and innovative approaches.
• Actively participate in design critiques and reviews, providing and receiving constructive feedback to elevate the quality of design work.
• Maintain and contribute to the ShareGate design system, ensuring adherence to established patterns, accessibility standards, and cross-product cohesion.
• Document design decisions, rationale, and specifications clearly to facilitate understanding and alignment across multidisciplinary teams.

📝 Enhancement Note: Responsibilities are framed to highlight leadership, strategic involvement, and deep collaboration, typical of a senior-level design role. The emphasis on translating "technical workflows" and designing for "IT professionals" is crucial for candidates to understand the specific user base and problem domain. The inclusion of AI and design system contributions points to a modern, evolving product development environment.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a Bachelor's or Master's degree in Design, Human-Computer Interaction, Computer Science, or a related field is often preferred for senior design roles. Equivalent practical experience will be considered.
Experience: A minimum of 6 years of professional experience in product design, with a significant focus on B2B SaaS products and cross-functional team collaboration.

Required Skills:

• End-to-End Design Leadership: Proven ability to lead design initiatives from conception through to polished execution within a product team.
• Complex Problem Solving: Demonstrated skill in navigating and simplifying ambiguous, technically complex problem spaces, particularly within enterprise software.
• User Experience (UX) Design: Expertise in user research, journey mapping, information architecture, and interaction design for B2B applications.
• User Interface (UI) Design: Strong visual design skills, including layout, typography, color theory, and creating intuitive interfaces.
• Prototyping & Iteration: Proficiency in creating interactive prototypes (e.g., using Figma, Sketch, Adobe XD) to validate concepts and iterate rapidly based on feedback.
• Cross-Functional Collaboration: Excellent collaboration skills, with a demonstrated ability to work effectively with Product Managers, Engineers, and other stakeholders.
• Communication & Storytelling: Ability to articulate design decisions clearly, present work effectively, and influence product and engineering partners through strong storytelling.
• Data-Informed Design: Experience using customer feedback, user data, product analytics, and support trends to guide design decisions.
• Design Systems: Familiarity with or experience contributing to design systems to ensure consistency and scalability.
• Attention to Detail: High level of precision and commitment to craft in all aspects of design work.

Preferred Skills:

• B2B SaaS Product Design: Specific experience designing for business-to-business software-as-a-service platforms.
• Technical Audience Design: Experience designing intuitive interfaces for technical users such as IT administrators, developers, or system engineers.
• AI-Powered Experience Design: Experience designing or contributing to the development of AI-driven features or user experiences.
• Microsoft 365 Ecosystem: Familiarity with the Microsoft 365 environment, including SharePoint, Exchange, and Teams, and their associated migration/governance challenges.
• Agile/Scrum Methodologies: Experience working within agile development environments.

📝 Enhancement Note: The qualifications section is structured to emphasize core design competencies vital for senior roles in B2B SaaS. The "Preferred Skills" are tailored to the specific domain of ShareGate Migrate, highlighting the advantage of experience with technical audiences and AI integration.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• End-to-End Case Studies: Showcase 2-3 comprehensive case studies detailing your design process from problem identification, research, ideation, design execution, and iteration to final outcomes. Focus on how you translated complex technical challenges into user-friendly solutions.
• Problem Framing & Solution Definition: Clearly articulate the problem space, user needs, and business objectives that guided your design decisions.
• Process & Methodology: Demonstrate your design thinking process, including user research methods, wireframing, prototyping, usability testing, and how you iterated based on findings.
• Collaboration & Influence: Provide examples of how you collaborated with Product Managers and Engineers, and how you influenced product direction or resolved design challenges through communication and partnership.
• Impact & Outcomes: Quantify the impact of your designs where possible (e.g., improved conversion rates, reduced support tickets, increased user adoption, efficiency gains).

Process Documentation:

• Workflow Analysis and Optimization: Exhibit examples of how you analyzed existing technical or user workflows and designed improvements to enhance efficiency and clarity.
• UI/UX Design Artifacts: Include examples of wireframes, high-fidelity mockups, and interactive prototypes that illustrate your design craft and attention to detail.
• Design System Contributions: If applicable, showcase contributions to design systems, style guides, or component libraries.
• AI Integration Examples: If possible, include examples or concepts that demonstrate your thinking around integrating AI into user experiences.

📝 Enhancement Note: Portfolio requirements are specific to a senior product designer role in a technical B2B SaaS context. Emphasis is placed on process, collaboration, and demonstrable impact, with a specific nod to AI integration and the complexity of technical workflows.

💵 Compensation & Benefits

Salary Range: $120,000 - $145,000 CAD per year.
Note on Salary: This range is based on ShareGate'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: Including medical, dental, and vision insurance.
• Retirement Savings Plan: Potential for employer matching contributions.
• Paid Time Off: Generous vacation days, sick leave, and public holidays.
• Professional Development: Opportunities for training, conferences, and learning resources to support skill advancement.
• Remote Work Stipend: Potential for a home office setup allowance or stipend.
• Employee Assistance Program (EAP): Support services for mental, physical, and financial well-being.
• Stock Options/Equity: Depending on the role and company policy, potential for equity participation.

Working Hours: Standard full-time hours, approximately 40 hours per week. The remote nature of the role offers flexibility in managing work hours, provided core collaboration needs and deliverables are met.

📝 Enhancement Note: The salary range is explicitly stated and contextualized with ShareGate's compensation philosophy. Benefits are tailored to what is typically offered by tech companies, especially those with a remote workforce.

🎯 Team & Company Context

🏢 Company Culture

Industry: Software Development, specifically focused on Microsoft 365 migration and governance solutions. This places ShareGate within the broader IT management and cloud services sector.
Company Size: Part of Workleap Technologies, a growing software company. While exact figures for ShareGate aren't specified, Workleap is a significant player, indicating a company with established processes but also room for agility and impact.
Founded: ShareGate was founded in 2006, with Workleap Technologies being its parent company. This history suggests a stable, experienced organization with a proven track record in the software market.

Team Structure:

• Product Trio Model: Designers work in close-knit, multidisciplinary teams comprising a Product Manager, Tech Lead, and Product Designer. This structure fosters deep collaboration and shared ownership.
• Design Team Collaboration: Designers are part of a larger design community within Workleap, likely interacting for critiques, knowledge sharing, and contributing to the central design system.
• Cross-Functional Integration: Designers are expected to integrate seamlessly with engineering and product management from early strategy phases through to development and release.

Methodology:

• Agile Development: Work is likely structured around agile methodologies, emphasizing iterative development, rapid feedback loops, and continuous learning.
• Data-Driven Decision Making: Design decisions are informed by user feedback, product analytics, support trends, and A/B testing.
• User-Centricity: A strong focus on understanding and solving the problems of IT professionals, ensuring the product is reliable, intuitive, and efficient.
• Continuous Improvement: A culture that encourages experimentation, learning from both successes and failures, and adapting processes and tools.

Company Website: https://sharegate.com/ (for product information) and https://www.workleap.com/ (for company information)

📝 Enhancement Note: The company context emphasizes the product's specific niche (Microsoft 365 migration/governance), the collaborative "product trio" model, and the agile/data-driven approach, all crucial for a designer to understand their working environment.

📈 Career & Growth Analysis

Operations Career Level: This role is classified as "Senior Product Designer," indicating a mid-to-senior level position. It requires a high degree of autonomy, ownership, and the ability to lead design initiatives with minimal supervision. The role involves strategic input rather than just execution.
Reporting Structure: The Senior Product Designer will likely report to a Design Lead, Head of Design, or a Product Management Lead, depending on the organizational structure. They will work within a product trio, collaborating closely with a Product Manager and Tech Lead.
Operations Impact: The Senior Product Designer will have a significant impact on the usability, adoption, and perceived reliability of the ShareGate Migrate product. By simplifying complex technical processes and exploring AI enhancements, they will directly influence customer success, operational efficiency for IT teams, and ultimately, revenue and market competitiveness.

Growth Opportunities:

• Design Leadership: Progression to Lead Product Designer, Design Manager, or specialize in areas like UX Research or Design Systems.
• Product Strategy Influence: Opportunity to shape the long-term product roadmap and strategy through design insights and innovation.
• AI Specialization: Develop expertise in designing AI-powered user experiences, a rapidly growing field.
• Mentorship: Opportunities to mentor junior designers and contribute to the growth of the design team.
• Broader Product Ecosystem Impact: Potential to contribute to the design of other products within the Workleap portfolio.

📝 Enhancement Note: This section frames the Senior Product Designer role within a clear career progression path, highlighting the strategic influence and opportunities for specialization, particularly in AI and technical product design.

🌐 Work Environment

Office Type: Fully Remote. This role operates entirely outside of a traditional office setting.
Office Location(s): While the role is remote, it is specified as "Canada-Remote." This implies candidates must be legally authorized to work in Canada and potentially reside within Canadian time zones to facilitate collaboration.

Workspace Context:

• Remote Collaboration Tools: Heavy reliance on digital collaboration tools (e.g., Microsoft Teams, Slack, Figma, Jira) for communication, design reviews, and project management.
• Flexible Work Schedule: The remote nature allows for flexibility in managing work hours, enabling better work-life integration, provided core meeting attendance and deliverable deadlines are met.
• Autonomous Work: Expectation of self-discipline, proactive communication, and the ability to manage one's own workload and schedule effectively.
• Virtual Team Interaction: Regular virtual meetings, design critiques, and team syncs to maintain connection and alignment within the product trio and the broader design team.

Work Schedule: Standard full-time, approximately 40 hours per week. Flexibility is offered within this framework, allowing individuals to structure their day, but availability for key meetings and collaborative sessions is essential.

📝 Enhancement Note: The remote aspect is central, with an emphasis on the tools and self-management skills required for success in a distributed work environment, alongside the implication of needing to align with Canadian time zones for collaboration.

📄 Application & Portfolio Review Process

Interview Process:

• Phone Screen: Initial conversation to assess basic qualifications, experience, and cultural fit.
• Virtual Interview (Microsoft Teams): Deeper dive into experience, design philosophy, and problem-solving approach. May include a portfolio walkthrough.
• Work Sample: A design exercise or challenge to evaluate practical design skills, problem-solving abilities, and strategic thinking. This is a critical component for senior roles.
• Job Offer: Final offer extended upon successful completion of all interview stages.

Portfolio Review Tips:

• Focus on Process, Not Just Polish: Clearly articulate your design process for each case study. Show how you arrived at your solutions, not just the final screens.
• Highlight Collaboration: Provide specific examples of how you partnered with PMs and engineers, and how you navigated disagreements or technical constraints.
• Quantify Impact: Where possible, use metrics to demonstrate the success of your designs. If direct metrics aren't available, articulate the intended business or user outcomes.
• Tailor to B2B & Technical Audiences: Emphasize projects that involved complex workflows, technical users, or B2B SaaS products. Showcase your ability to simplify intricate systems.
• Showcase AI Thinking: If you have relevant experience, highlight your approach to designing AI-powered features or how you'd leverage AI in the ShareGate context.
• Be Prepared to Discuss: Anticipate questions about your design decisions, trade-offs made, and lessons learned.

Challenge Preparation:

• Understand the Domain: Research ShareGate, its products (especially Migrate), and the challenges of Microsoft 365 migration and governance. Understand the target user (IT Administrators).
• Practice Problem Decomposition: Be ready to break down a complex problem into smaller, manageable parts.
• Articulate Trade-offs: Demonstrate your ability to balance user needs, business goals, technical constraints, and timelines.
• Think Strategically: Consider how your design solution fits into the broader product strategy and user journey.
• Communicate Clearly: Practice presenting your thought process and solutions concisely and effectively.

📝 Enhancement Note: This section provides actionable advice for candidates, focusing on the specific expectations for a senior product designer interview, including portfolio presentation and handling design challenges relevant to ShareGate's domain.

🛠 Tools & Technology Stack

Primary Design Tools:

• Figma: Expected to be the primary tool for UI design, prototyping, and collaboration.
• Sketch / Adobe XD: Proficiency in these or similar industry-standard design tools is also valuable.
• Prototyping Tools: Beyond Figma, experience with dedicated prototyping tools for more complex interactions.
• AI Prototyping Tools: Explicitly mentioned as a tool to be utilized regularly. Candidates should be aware of emerging AI-powered design tools.

Collaboration & Project Management:

• Microsoft Teams: For communication and virtual meetings.
• Jira / Confluence: Likely used for issue tracking, documentation, and workflow management.
• Slack: Potentially used for team communication.

Data Analysis & Insights:

• Product Analytics Platforms: Experience with tools like Amplitude, Mixpanel, or similar for understanding user behavior.
• Customer Feedback Platforms: Familiarity with tools or methods for collecting and analyzing user feedback.
• Support Ticket Systems: Understanding how to leverage insights from customer support data.

Design System Tools:

• Storybook (or similar): Often used for documenting and managing design system components.

📝 Enhancement Note: This section details the expected technology stack, emphasizing design tools like Figma and AI prototyping tools, alongside collaboration and analytics platforms crucial for a remote, data-informed design role.

👥 Team Culture & Values

Operations Values:

• Curiosity & Boldness: A drive to explore new ideas and boldly tackle complex challenges.
• Simplicity & Clarity: A commitment to making complex technical processes "just damn simple."
• Customer Centricity: Keeping customers (IT professionals) at the center of all product decisions.
• Collaboration & Trust: Working together, trusting each other, and supporting team members.
• Continuous Learning & Growth: Embracing experimentation, rapid learning, and pushing boundaries for personal and product development.
• Ownership & Proactivity: Taking responsibility for work and proactively seeking solutions.

Collaboration Style:

• Partnership: Close, collaborative partnerships within the product trio (PM, Tech Lead, Designer) and with the broader engineering team.
• Feedback-Rich Environment: Openness to giving and receiving constructive feedback through critiques and reviews.
• Transparency: Clear communication of ideas, decisions, and rationale across teams.
• Cross-functional Integration: Design is not siloed but integrated into the core product development process.

📝 Enhancement Note: The company values are explicitly stated and translated into behavioral expectations for designers, emphasizing a collaborative, user-focused, and growth-oriented culture.

⚡ Challenges & Growth Opportunities

Challenges:

• Designing for Technical Complexity: Translating highly technical and often ambiguous Microsoft 365 migration and governance processes into intuitive user experiences.
• Balancing Speed and Quality: Delivering high-quality, thoughtful designs in a fast-paced, agile environment.
• Enterprise-Scale Scenarios: Designing solutions that can handle the complexity and scale required by enterprise clients.
• Evolving AI Integration: Strategically integrating AI in a way that genuinely benefits users and enhances the product without becoming a gimmick.
• Cross-Product Cohesion: Ensuring design consistency and a unified experience across the ShareGate product suite and its evolving design system.

Learning & Development Opportunities:

• Deep Domain Expertise: Become an expert in Microsoft 365 migration and governance, a critical area for many organizations.
• AI Design Specialization: Gain hands-on experience designing and implementing AI-powered features, a highly sought-after skill.
• Design System Leadership: Contribute significantly to a growing design system, influencing its direction and impact.
• Strategic Product Influence: Opportunity to shape product strategy and roadmap through design leadership.
• Cross-Functional Skill Development: Enhance skills in product strategy, technical feasibility, and agile development processes.

📝 Enhancement Note: This section highlights the specific challenges inherent in the role and the product domain, linking them directly to growth opportunities for the Senior Product Designer.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you translated a highly technical or ambiguous workflow into a simple, intuitive user experience. What was your process?" (Focus on problem framing, user research, and iterative design).
• "How would you approach designing an AI-powered feature to help IT administrators predict migration risks?" (Focus on understanding user needs, potential AI applications, and user experience design principles for AI).
• "Walk me through a complex B2B SaaS product you designed. What were the key challenges, how did you collaborate with PMs and engineers, and what was the outcome?" (Emphasize end-to-end ownership, collaboration, and impact).

Company & Culture Questions:

• "What interests you about ShareGate and our mission to simplify Microsoft 365 migration?" (Show research into the product and company values).
• "How do you approach design critiques and incorporating feedback, especially when it conflicts with your initial ideas?" (Assess collaboration style and openness to feedback).
• "Describe your experience working in a remote, cross-functional team. What strategies do you use to stay aligned and effective?" (Highlight communication, organization, and collaboration skills).

Portfolio Presentation Strategy:

• Start with the 'Why': Begin each case study by clearly stating the problem, user needs, and business goals.
• Show Your Process: Dedicate significant time to explaining your research, ideation, and iteration stages. Use visuals like user journey maps, wireframes, and testing insights.
• Highlight Collaboration: Clearly indicate where and how you worked with PMs and engineers.
• Focus on Impact: Conclude by detailing the outcomes and lessons learned. Quantify results if possible.
• Be Prepared for Deep Dives: Expect questions on specific design decisions, trade-offs, and alternative solutions you considered.

📝 Enhancement Note: These interview preparation points are tailored to the Senior Product Designer role, focusing on technical complexity, AI integration, B2B SaaS context, and the collaborative remote environment.

📌 Application Steps

To apply for this Senior Product Designer position:

• Submit your application through the provided greenhouse.io link.
• Portfolio Customization: Ensure your portfolio prominently features 2-3 detailed case studies showcasing your end-to-end design process, with a focus on complex B2B SaaS products and technical audiences.
• Resume Optimization: Tailor your resume to highlight your 6+ years of experience in product design, specifically mentioning B2B SaaS, UI/UX, prototyping, collaboration, and any experience with AI or technical tools.
• Prepare for a Design Challenge: Be ready to tackle a design exercise that assesses your ability to solve complex problems, think strategically, and communicate your design process effectively.
• Research ShareGate: Familiarize yourself with ShareGate's products, target audience (IT administrators), and the challenges of Microsoft 365 migration/governance to demonstrate genuine interest and understanding.

⚠️ 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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