Senior Web Designer

📍 Job Overview

Job Title: Senior Web Designer

Company: Winona

Location: Canada (Remote)

Job Type: FULL_TIME

Category: Web Design / UX/UI Design

Date Posted: March 31, 2026

Experience Level: Senior Level (5+ Years)

Remote Status: Fully Remote

🚀 Role Summary

• Lead end-to-end design strategy and execution for complex web projects, ensuring alignment with business objectives and a superior user experience.

• Translate strategic briefs into high-fidelity, user-centered designs using Figma, adhering strictly to established design systems and best practices.

• Collaborate closely with product managers, developers, and stakeholders to ensure design feasibility, consistency, and successful implementation across digital platforms.

• Contribute to the evolution and maintenance of design systems, upholding a cohesive visual language and scalable design framework.

📝 Enhancement Note: While the title is "Senior Web Designer," the responsibilities emphasize a holistic UX/UI design approach, including strategic leadership, user research, and collaboration with product and development teams. This role is more than just visual design; it requires a strategic thinker who can drive user experience from concept to implementation within a fast-paced, remote environment. The target audience for this role is a seasoned designer with a strong understanding of product development lifecycles.

📈 Primary Responsibilities

• Spearhead the complete design lifecycle for intricate web initiatives, from conceptualization through to final deployment, ensuring strategic alignment with Winona's business goals.

• Develop and champion innovative design strategies that elevate user experience and directly support core business objectives, particularly in the telemedicine and HRT space.

• Craft detailed wireframes and high-fidelity mockups in Figma, meticulously implementing our design system and adhering to user-centered design principles.

• Ensure all designs are fully responsive, accessible (WCAG compliant), and optimized for a seamless user journey across diverse devices and platforms.

• Foster strong collaborative relationships with product managers, engineers, and marketing teams, facilitating clear communication and ensuring design solutions are technically feasible and aligned with project scope.

• Actively contribute to the growth and refinement of Winona's design system, ensuring consistency, scalability, and adherence to brand guidelines across all digital touchpoints.

• Conduct user research, journey mapping, and A/B testing to validate design hypotheses, gather insights, and drive data-informed design decisions that optimize conversion rates and user engagement.

• Manage project priorities effectively, coordinating with project managers to ensure timely delivery of high-quality design assets within agile development cycles.

• Stay current with emerging design trends, technologies, and best practices, proactively identifying opportunities for innovation and continuous improvement in user experience and design methodologies.

• Perform rigorous quality assurance on implemented designs, validating that they meet user needs, project specifications, and established design standards.

📝 Enhancement Note: The responsibilities are heavily focused on strategic design leadership, user-centricity, and cross-functional collaboration, indicating a role that requires not just execution but also strategic input and ownership. The emphasis on design systems, user research, and A/B testing points to a data-driven approach to design, which is crucial for optimizing conversion funnels in a digital health context.

🎓 Skills & Qualifications

Education: Not explicitly specified, but a degree in Design, Human-Computer Interaction, or a related field is often preferred for senior roles.

Experience: 5+ years of dedicated experience in UX/UI design, with a significant focus on web design and digital product development.

Required Skills:

• Demonstrated expertise in UX/UI design principles, with a strong portfolio showcasing impactful, user-centered website designs.

• Advanced proficiency in design and prototyping tools, specifically Figma, and a strong working knowledge of Adobe Illustrator and Photoshop.

• Deep understanding of design systems, their architecture, and their application in maintaining brand consistency and scalability across digital products.

• Comprehensive knowledge of responsive design principles, ensuring optimal user experiences across all devices (desktop, tablet, mobile).

• Solid grasp of core UX principles, interaction design patterns, and information architecture best practices.

• Proven ability to collaborate effectively with cross-functional teams, including product managers and developers, to translate requirements into seamless user experiences.

• Exceptional attention to detail, organizational skills, and the proven ability to manage multiple complex projects simultaneously.

• Experience working within fast-paced, agile development environments, adapting quickly to changing priorities and project scopes.

• Skilled in utilizing user research methodologies, journey mapping, and A/B testing to inform design decisions and measure impact.

Preferred Skills:

• Basic understanding of HTML, CSS, and JavaScript, facilitating better collaboration with development teams.

• Experience in contributing to the development or significant scaling of design systems.

• Experience within the telemedicine, healthcare, or regulated industries, understanding specific user needs and compliance requirements.

📝 Enhancement Note: The requirements highlight a blend of technical design skills, strategic thinking, and collaborative abilities. The emphasis on Figma, design systems, and user research/testing suggests a modern, data-driven design workflow. The preference for basic HTML/CSS/JS knowledge and experience in healthcare is a strong indicator of the company's operational context and desired candidate profile.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A robust portfolio demonstrating a strong track record of user-centered, high-impact website designs, showcasing the entire design process from discovery to execution.

• Detailed case studies that clearly articulate the design problem, your strategic approach, the solutions implemented, and the measurable impact on user experience and business goals.

• Examples of complex web projects, highlighting your ability to handle intricate user flows, information architecture challenges, and responsive design implementation.

Process Documentation:

• Evidence of your process for translating strategic briefs into actionable design deliverables, including wireframes, user flows, and high-fidelity mockups.

• Examples of how you've applied user research, journey mapping, and A/B testing to inform and validate design decisions, showing a data-driven approach to problem-solving.

• Documentation or examples of how you've contributed to or utilized design systems, illustrating your understanding of consistency, scalability, and component-based design.

📝 Enhancement Note: For a senior design role, the portfolio is paramount. It needs to go beyond aesthetics and demonstrate strategic thinking, problem-solving skills, and a deep understanding of the user-centered design process. The emphasis on case studies and data-informed decisions is critical for showcasing the candidate's ability to drive tangible business outcomes.

💵 Compensation & Benefits

Salary Range: Based on industry benchmarks for Senior Web Designers in Canada, with remote work flexibility across LATAM and Canada, and considering the senior level, an estimated annual salary range would be CAD $90,000 - $130,000. This range can fluctuate based on specific experience, the candidate's location within these regions, and their proven impact.

Benefits:

• Unlimited Paid Time Off: Offers flexibility and autonomy, allowing employees to manage their work-life balance effectively.

• Paid Non-Working Holidays Per Country Of Residence: A thoughtful benefit that acknowledges and respects diverse international employee locations.

• Pro-Rated 13th-Month Bonus In Select Regions: Provides additional financial compensation, a common practice in some of the specified LATAM countries.

• Referral Bonuses: Encourages employee engagement and leverages the network for talent acquisition.

• Financial Support For Online Courses: Supports continuous learning and professional development, crucial for staying current in design.

• Fun And Casual Work Environment: Fosters a relaxed and collaborative atmosphere, promoting creativity and team cohesion.

• Employee Engagement Activities And Virtual Gatherings: Aims to build community and combat isolation in a remote setting.

Working Hours: 40 hours per week, with flexibility inherent in a remote-first, global team environment.

📝 Enhancement Note: Salary estimation is based on typical senior UX/UI designer compensation in Canada, a primary stated location. The inclusion of LATAM countries for remote work may necessitate adjustments based on local market rates and cost of living, but the CAD range provides a strong benchmark. The benefits package is robust, emphasizing work-life balance, professional growth, and a positive remote culture.

🎯 Team & Company Context

🏢 Company Culture

Industry: Healthcare Technology (Telemedicine, HRT for Women in Menopause). Winona operates in a growing and impactful sector, leveraging technology to provide essential healthcare services. This industry demands a high degree of user trust, data security, and empathy in design.

Company Size: While not explicitly stated, the mention of building all technology in-house (EHR, patient portal, etc.) and operating compounding pharmacies suggests a company that has scaled significantly beyond a startup phase and has established operational complexity. It's likely a mid-sized to large organization with dedicated departments.

Founded: Founded in 2019, Winona is a relatively young but rapidly growing company, indicating a dynamic, innovative, and potentially fast-paced environment.

Team Structure:

• The design team likely operates within a Product or Engineering department, working closely with Product Managers and Developers.

• As a Senior Web Designer, you may have opportunities to mentor junior designers or lead specific project streams, depending on the team's hierarchy.

Methodology:

• Data-Driven Design: The emphasis on user research, journey mapping, and A/B testing points to a methodology that prioritizes data and user feedback in design decisions.

• Agile Development: Experience in agile environments is a requirement, suggesting iterative design and development cycles.

• In-House Technology Development: Building proprietary technology implies a strong focus on internal innovation, technical excellence, and integrated solutions.

Company Website: https://bywinona.com/

📝 Enhancement Note: Understanding Winona's industry (telemedicine for women's health) is crucial. Design decisions must be made with sensitivity, a focus on patient well-being, and an understanding of healthcare compliance. The company's in-house tech development suggests a culture of innovation and control over its user experience.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned as "Senior Level," indicating a significant degree of autonomy, strategic input, and responsibility. A Senior Web Designer is expected to lead complex projects, mentor others, and contribute to the overall design strategy and standards of the company.

Reporting Structure: The role will likely report to a Design Lead, Head of Product Design, or potentially a Director of Product/Engineering. Close collaboration with Product Managers and development teams is a key aspect of the role's day-to-day operations.

Operations Impact: The Senior Web Designer directly influences Winona's primary touchpoints with its users—the website and potentially other digital interfaces. Their work will impact patient acquisition, engagement, satisfaction, and overall brand perception. By creating user-centered, effective designs, they contribute directly to the company's mission of providing accessible HRT for women and its overall business growth and revenue.

Growth Opportunities:

• Design Leadership: Potential to grow into a Lead Designer or Design Manager role, overseeing a team and setting design direction for larger initiatives.

• Specialization: Opportunity to deepen expertise in specific areas like UX research, design systems, or interaction design within the healthcare tech domain.

• Cross-Functional Expertise: Develop a deeper understanding of product management, engineering, and marketing within a fast-growing tech company.

• Mentorship: Opportunity to mentor junior designers, developing leadership and coaching skills.

📝 Enhancement Note: The "Senior" designation implies expectations of leadership, strategic contribution, and the ability to operate independently. Growth paths within a growing tech company like Winona could involve moving into management, specializing further, or taking on broader product strategy roles.

🌐 Work Environment

Office Type: Remote-first. This means the primary work environment is digital, with no central physical office required for daily operations.

Office Location(s): While the role is remote, the company operates globally, with employees located in Canada, Mexico, Argentina, Brazil, and Colombia. This implies a diverse, distributed team environment.

Workspace Context:

• Collaborative Digital Environment: Expect to use communication and collaboration tools (e.g., Slack, Zoom, Asana/Jira) extensively to interact with team members across different time zones.

• Technology Stack: Access to industry-standard design tools (Figma, Adobe Suite) and project management software will be provided or expected.

• Team Interaction: Regular virtual team meetings, design critiques, and cross-functional syncs will be essential for staying connected and aligned.

Work Schedule: While a standard 40-hour work week is mentioned, the remote-first nature with global team members suggests a degree of flexibility in daily scheduling, provided core responsibilities are met and collaboration across time zones is managed effectively.

📝 Enhancement Note: The "remote-first" nature is a key characteristic. Candidates should be comfortable with asynchronous communication, self-discipline, and leveraging digital tools to collaborate. The global distribution of the team means cultural awareness and adaptability will be important.

📄 Application & Portfolio Review Process

Interview Process:

• Application Submission: Submit resume and portfolio via the provided link.

• Initial Screening: A recruiter or hiring manager will review applications and portfolios for fit with requirements.

• Portfolio Review & Interview: Expect a deep dive into your portfolio, focusing on case studies, design process, and problem-solving approaches. This will likely involve a conversation with the hiring manager or a senior designer.

• Design Challenge/Assignment: You may be given a small design exercise or asked to present a hypothetical solution to a design problem relevant to Winona's business.

• Cross-Functional Interviews: Interviews with Product Managers and/or Developers to assess collaboration skills and technical understanding.

• Final Interview: Potentially with a senior leader (e.g., Head of Product, CTO) to discuss strategic alignment and cultural fit.

Portfolio Review Tips:

• Curate Strategically: Select 3-5 of your strongest, most relevant projects that showcase your end-to-end design process, user-centric approach, and impact. Prioritize web design projects.

• Tell a Story: For each project, clearly articulate the problem, your role, your process (research, ideation, iteration, testing), the challenges faced, and the final solution. Use visuals effectively.

• Quantify Impact: Wherever possible, include metrics and data to demonstrate the success of your designs (e.g., increased conversion rates, improved user satisfaction scores, reduced bounce rates).

• Highlight Figma & Design Systems: Showcase your proficiency with Figma and any experience with design systems, as these are key requirements.

• Be Ready to Discuss: Prepare to walk through your portfolio and answer detailed questions about your design decisions, rationale, and how you handle feedback.

Challenge Preparation:

• Understand Winona: Research Winona's services, target audience (women in menopause), and overall brand.

• Focus on User Needs: For any hypothetical challenge, emphasize understanding the user's needs and pain points first.

• Demonstrate Process: Clearly outline your design process, even for a hypothetical scenario.

• Consider Constraints: Acknowledge technical or business constraints and how you would navigate them.

📝 Enhancement Note: The interview process is likely structured to thoroughly assess design skills, strategic thinking, and collaborative capabilities. The portfolio is the central piece, and candidates must be prepared to discuss their work in depth, demonstrating a data-driven and user-centered approach.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: The core design and prototyping tool. Proficiency is essential for creating high-fidelity mockups, interactive prototypes, and design system components.

• Adobe Illustrator: Likely used for creating vector graphics, icons, and illustrations.

• Adobe Photoshop: For image editing, manipulation, and potentially creating complex visual assets.

Analytics & Reporting:

• User Research Tools: Tools for conducting user interviews, surveys, and usability testing (e.g., UserTesting.com, SurveyMonkey, Lookback).

• A/B Testing Platforms: Experience with platforms like Google Optimize, Optimizely, or VWO for testing design variations.

• Analytics Platforms: Familiarity with web analytics tools like Google Analytics to understand user behavior and measure design impact.

CRM & Automation:

• Project Management Software: Tools like Asana, Jira, or Trello for managing design tasks, workflows, and collaborating with development teams.

• Communication Platforms: Slack, Microsoft Teams, or similar for real-time team communication.

📝 Enhancement Note: The explicit mention of Figma, Illustrator, and Photoshop points directly to the expected technical toolkit. Familiarity with A/B testing and user research tools is crucial given the role's emphasis on data-informed design. Project management tools are standard for remote collaboration.

👥 Team Culture & Values

Operations Values:

• User-Centricity: A core value that prioritizes understanding and meeting the needs of patients seeking HRT services. Designs should be empathetic, intuitive, and trustworthy.

• Innovation & Efficiency: As a tech-forward telemedicine company, Winona likely values creative problem-solving and efficient processes to deliver care and scale its services.

• Data-Driven Decision Making: The requirement for user research and A/B testing highlights a culture that relies on data to inform strategy and validate design choices.

• Collaboration & Transparency: A remote, global team requires strong communication, openness, and a willingness to work together across different locations and time zones.

• Impact & Mission-Driven: Working in healthcare, especially women's health, suggests a culture that values making a tangible positive impact on people's lives.

Collaboration Style:

• Remote-First & Asynchronous: Expect a significant amount of collaboration to occur asynchronously via project management tools and communication platforms, with scheduled synchronous meetings for key discussions and decision-making.

• Cross-Functional Integration: Designers are expected to work closely with Product, Engineering, and potentially Marketing, requiring strong communication and the ability to translate technical and business needs into design solutions.

• Feedback-Oriented: A culture that likely encourages constructive feedback on designs through critiques and reviews to ensure high quality and alignment.

📝 Enhancement Note: The company's mission in women's health and its remote-first structure will heavily influence its culture. Empathy, data-driven insights, and strong remote collaboration are likely key pillars.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing User Needs with Business Goals: Effectively integrating patient needs with Winona's business objectives in a regulated healthcare environment.

• Design System Evolution: Contributing to and scaling a design system for a rapidly growing, multi-faceted digital product suite.

• Cross-Time Zone Collaboration: Managing communication and project flow effectively with a distributed global team.

• Staying Ahead of Design Trends: Continuously innovating in a competitive digital health landscape.

• Translating Complex Medical Concepts: Designing intuitive interfaces for potentially complex medical information and processes.

Learning & Development Opportunities:

• Advanced Design System Mastery: Deepening expertise in design system architecture, governance, and implementation.

• UX Research & Data Analysis: Enhancing skills in user research methodologies and interpreting analytics to drive design strategy.

• Leadership & Mentorship: Opportunities to lead design initiatives and mentor junior team members.

• Industry-Specific Design: Gaining specialized knowledge in designing for the healthcare and telemedicine sectors.

• Access to Online Courses: Leveraging the provided financial support for continuous skill enhancement.

📝 Enhancement Note: The challenges are typical for a senior role in a growing tech company, especially in a regulated industry. The growth opportunities are clear, focusing on leadership, specialization, and continuous learning.

💡 Interview Preparation

Strategy Questions:

• "Walk me through a complex web project from your portfolio. What was the business problem, your approach, how did you use Figma, and what was the outcome?" (Focus on demonstrating your process, problem-solving, and impact.)

• "How do you approach translating a strategic brief into actionable design deliverables? Describe your process for wireframing and high-fidelity mockups." (Highlight your strategic thinking and execution workflow.)

• "Describe your experience with design systems. How have you contributed to or utilized them to ensure consistency and scalability?" (Emphasize your understanding of system design and its benefits.)

Company & Culture Questions:

• "What interests you about Winona and our mission in women's health?" (Research Winona's services and values.)

• "How do you approach collaboration with product managers and developers, especially in a remote environment?" (Prepare examples of successful cross-functional teamwork.)

Portfolio Presentation Strategy:

• Structure: For each project, follow a clear narrative: Problem -> Your Role/Process -> Solution -> Impact/Results.

• Visuals: Use high-quality mockups, wireframes, user flows, and prototypes to illustrate your points.

• Figma Focus: Be prepared to show your Figma files or explain your workflow within the tool.

• Metrics: Quantify the success of your projects with data whenever possible.

• Conciseness: Keep your presentation focused and engaging, respecting the interviewer's time.

📝 Enhancement Note: Interview preparation should focus on articulating your design process, showcasing your strategic thinking, and demonstrating your ability to collaborate effectively within a remote, product-focused team.

📌 Application Steps

To apply for this operations position:

• Submit your application through the application link provided.

• Portfolio Customization: Tailor your portfolio to highlight 3-5 of your strongest web design projects, emphasizing user-centered solutions, your design process in Figma, and measurable outcomes.

• Resume Optimization: Ensure your resume clearly showcases 5+ years of relevant UX/UI and web design experience, using keywords from the job description such as "Figma," "design systems," "responsive design," and "user research."

• Interview Preparation: Practice walking through your portfolio projects, articulating your design rationale, and preparing answers for common interview questions about collaboration, problem-solving, and your approach to design challenges.

• Company Research: Thoroughly research Winona's services, target audience, and company mission to demonstrate genuine interest and articulate how your skills align with their goals in the telemedicine space.

⚠️ 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.