Senior Content Designer

📍 Job Overview

Job Title: Senior Content Designer

Company: Sidekick

Location: Toronto, Ontario, Canada

Job Type: Full-time

Category: Content Strategy & Design / User Experience

Date Posted: 2026-01-16

Experience Level: 10+ Years

Remote Status: Hybrid

🚀 Role Summary

• This role focuses on enhancing the customer journey by strategically structuring and delivering educational content across web and app platforms, aiming to improve user confidence and product adoption.

• The Senior Content Designer will be instrumental in identifying and resolving user confusion points, thereby directly impacting conversion rates and customer satisfaction.

• A key responsibility involves translating user needs and educational requirements into tangible design solutions, including wireframes and refined copy.

• This position demands a blend of analytical thinking to interpret data and strong design intuition to create intuitive, user-centric educational experiences.

📝 Enhancement Note: While the title is "Senior Content Designer," the responsibilities heavily lean into UX strategy, information architecture, and conversion rate optimization (CRO). The role requires a deep understanding of how content directly influences user behavior and business outcomes, particularly in an e-commerce context. The "10+ Years" experience level suggests a senior individual contributor role with significant autonomy and strategic input.

📈 Primary Responsibilities

• Customer Journey Education Ownership: Envision, design, and implement educational content strategies across product detail pages (PDPs), landing pages, email flows, and the mobile application to ensure users receive timely and relevant information.

• User Confusion Identification & Resolution: Proactively identify points of customer confusion, hesitation, or uncertainty throughout their journey and design/implement solutions to address these friction points.

• Design & Wireframing: Translate educational content vision into practical wireframes and collaborate closely with UI/UX designers to bring these concepts to life, ensuring a seamless and intuitive user experience.

• Educational Copywriting: Develop and refine clear, concise, and impactful educational copy that simplifies complex physiotherapy concepts into easily understandable human language for a broad audience.

• Content Simplification & Optimization: Continuously review and simplify existing content, or remove redundant information, that may add friction or overwhelm users, prioritizing clarity and effectiveness.

• Conversion Rate Optimization (CRO): Leverage data-informed decisions and UX best practices to optimize educational content for improved e-commerce conversion rates and reduced pre-purchase inquiries.

• Cross-Functional Collaboration: Work closely with Product, Marketing, and leadership teams to align educational content strategy with broader business objectives and user experience goals.

📝 Enhancement Note: The responsibilities highlight a strategic approach to content, focusing on its role as a growth lever rather than just informational dissemination. The emphasis on "simplification" and "reducing friction" indicates a strong CRO and UX focus. Collaboration with Product and Marketing suggests this role sits at a critical intersection of user understanding and business strategy.

🎓 Skills & Qualifications

Education:

Experience:

• Minimum of 7 years of proven experience in improving e-commerce conversion rates through Conversion Rate Optimization (CRO) and user experience (UX) design decisions.

Required Skills:

• UX/UI Design: Demonstrated expertise in designing user-centered interfaces and workflows, with a strong portfolio showcasing successful UX initiatives.

• Information Architecture: Ability to structure and organize content logically to enhance navigability and user comprehension across digital platforms.

• Wireframing & Prototyping: Proficiency in creating detailed wireframes and interactive prototypes to visualize content solutions and user flows (e.g., using Figma).

• Educational Copywriting: Exceptional writing skills with a proven ability to translate complex technical or scientific information into clear, accessible, and engaging educational content.

• Conversion Rate Optimization (CRO): Strong understanding of CRO principles and methodologies, with a track record of implementing changes that drive measurable improvements in conversion rates.

• Data-Informed Decision Making: Ability to interpret user data, analytics, and A/B test results to inform design decisions, while also exercising sound judgment and intuition.

• Communication & Simplification: Excellent verbal and written communication skills, with a talent for simplifying complex ideas and content.

• Collaboration: Proven ability to work effectively in a cross-functional team environment, collaborating with designers, product managers, and marketers.

Preferred Skills:

• Figma Proficiency: Advanced skills in Figma or similar design tools for wireframing, prototyping, and design collaboration.

• Customer Journey Mapping: Experience in mapping and optimizing the entire customer journey, with a focus on educational touchpoints.

• E-commerce Platform Experience: Familiarity with e-commerce platforms and their specific content and UX challenges.

• Physiotherapy/Health Industry Knowledge: Basic understanding of physiotherapy concepts or the health and wellness industry is a plus.

📝 Enhancement Note: The requirement for "7+ years of experience improving e-commerce conversion through CRO and UX decisions" and "7+ years of UX/UI experience" combined with the "10+ Years" overall AI experience level strongly suggests a senior individual contributor role. The emphasis on data-informed decisions balanced with judgment indicates a need for strategic thinkers who can navigate ambiguity.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• CRO Case Studies: Showcase at least 2-3 detailed case studies demonstrating how you improved e-commerce conversion rates through content and UX design interventions. Clearly articulate the problem, your approach, the specific content/design solutions implemented, and the quantifiable results (e.g., conversion lift, reduced bounce rate, increased time on page).

• Information Architecture Examples: Provide examples of how you have structured complex information or educational content for clarity and ease of use on digital platforms. This could include sitemaps, content hierarchy diagrams, or flowcharts.

• Wireframing & Design Samples: Include samples of wireframes and user flows you have designed, ideally for educational content or complex user journeys. Highlight your ability to translate strategic requirements into visual design concepts.

• Copywriting Samples: Present examples of educational copywriting, particularly where you've simplified complex topics for a general audience. Focus on clarity, tone, and effectiveness in driving user understanding and confidence.

• Data Analysis Integration: Demonstrate how you have used data (e.g., analytics, A/B test results, user feedback) to inform your design and content decisions within your portfolio pieces.

Process Documentation:

• Content Strategy & Design Process: Outline your systematic approach to developing and implementing educational content strategies, from initial research and ideation to final execution and iteration.

• User Research & Problem Identification: Describe your methods for identifying user pain points and areas of confusion, and how you translate these insights into actionable design solutions.

• Collaboration & Handoff: Detail your process for collaborating with UI/UX designers and other stakeholders, including how you communicate design intent and ensure smooth handoffs for implementation.

📝 Enhancement Note: For a Senior Content Designer role with strong UX and CRO components, the portfolio is critical. It needs to demonstrate not just design skills but a strategic understanding of how content drives business metrics. Emphasis should be on quantifiable results and a clear, repeatable process for content strategy and design.

💵 Compensation & Benefits

Salary Range:

• Estimated Range: $90,000 - $130,000 CAD per year.

• Methodology: This estimate is based on market research for Senior Content Designers and UX/CRO specialists in Toronto, Canada, considering the indicated experience level (10+ years), hybrid work arrangement, and company size/stage (implied by "rapid growth" and "high ownership"). The range accounts for variations in specific responsibilities and the candidate's negotiation.

Benefits:

• Competitive Compensation: Includes a competitive base salary and a performance-based bonus, recognizing individual and company achievements.

• Comprehensive Health Benefits: Full health, dental, and vision coverage to support employee well-being.

• High Ownership & Autonomy: Significant decision-making power and autonomy in defining and executing educational content strategies.

• Direct Collaboration: Opportunity to work directly with product, marketing, and leadership teams, providing high visibility and impact.

• Growth Opportunities: Potential to define and scale education across both web and app platforms, offering significant career development.

• Supportive Colleagues: Access to dedicated, collaborative, and supportive team members in a fast-paced environment.

Working Hours:

• Standard full-time hours, estimated at 40 hours per week. The hybrid nature of the role offers flexibility with work-from-home days.

• 📝 Enhancement Note: The "Hybrid role with work-from-home flexibility" implies a structured office presence is expected, likely with a set number of days per week, though not explicitly defined.

🎯 Team & Company Context

🏢 Company Culture

Industry: Health & Wellness / E-commerce / Medical Devices (Rehabilitation)

Company Size: Estimated 50-150 employees (based on LinkedIn data for Sidekick and typical growth stages for companies with this level of funding/traction). This size suggests a dynamic environment where individual contributions have a significant impact.

Founded: Sidekick was founded in 2018, indicating a relatively young but established company that has moved beyond the early startup phase and is now focused on scaling.

Team Structure:

• Operations Team Aspect 1: The Content Design role likely sits within a broader Product or Marketing team, collaborating closely with UI/UX Designers, Product Managers, and Marketing Specialists.

• Operations Team Aspect 2: Reporting structure is likely to a Head of Product, Director of Marketing, or a similar senior leadership role overseeing user experience and customer communication.

• Operations Team Aspect 3: Cross-functional collaboration is a cornerstone, with frequent interaction across product development, user research, marketing campaigns, and customer support functions to ensure a cohesive educational experience.

Methodology:

• Data-Driven Optimization: A strong emphasis on using data (analytics, A/B testing, user feedback) to inform decisions and measure the impact of content and design changes.

• User-Centric Design: Prioritizing the user's needs, understanding their journey, and designing solutions that address their pain points and build confidence.

• Iterative Improvement: A culture of continuous learning and refinement, where content and designs are regularly reviewed, tested, and improved based on performance and user feedback.

Company Website: https://meetsidekick.com/

📝 Enhancement Note: Sidekick's mission to help people recover from injuries positions it within the health-tech and direct-to-consumer wellness space. The product-heavy nature of their offering means educational content is not an afterthought but a critical component of their go-to-market and customer success strategy. The company appears to have a strong product-market fit and is in a growth phase, emphasizing impact and ownership.

📈 Career & Growth Analysis

Operations Career Level: Senior Individual Contributor. This role is for an experienced professional who can operate with a high degree of autonomy, driving strategy and execution in their domain. It's not a management role but one that influences direction through expertise.

Reporting Structure: Likely reports to a Director of Product, Head of Marketing, or a similar senior leader who champions user experience and customer-centric growth. Direct collaboration with Product and Marketing leadership is expected.

Operations Impact: This role has a direct and measurable impact on key business metrics such as e-commerce conversion rates, customer acquisition cost (CAC) by reducing pre-purchase inquiries, customer retention (through better product utilization), and overall brand perception by building trust and clarity.

Growth Opportunities:

• Strategic Leadership: Opportunity to define and evolve Sidekick's entire educational content strategy across multiple platforms, becoming a subject matter expert and key influencer within the company.

• Skill Specialization: Deepen expertise in content design, UX strategy, information architecture, and conversion rate optimization within the health-tech and e-commerce sectors.

• Cross-Functional Influence: Expand influence by collaborating closely with product development, marketing campaigns, and customer success initiatives, potentially leading to broader product or marketing strategy roles.

• Team Development: As the company scales, there may be opportunities to mentor junior designers or content specialists, or to shape the future of the content design function.

📝 Enhancement Note: The "Senior" title and "High ownership" benefit point to a role where the individual is expected to be a thought leader and executor. Growth opportunities will likely stem from mastering this domain and expanding influence within a growing company, rather than necessarily moving into people management early on.

🌐 Work Environment

Office Type: Hybrid. This indicates a blend of remote work and in-office collaboration, suggesting a need for strong remote communication skills alongside in-person teamwork.

Office Location(s): Toronto, Ontario, Canada. The specific office location within Toronto would be beneficial for candidates to understand commute and local amenities.

Workspace Context:

• Collaborative Environment: The hybrid model and emphasis on cross-functional collaboration suggest an office designed to facilitate teamwork, brainstorming, and connection. Expect spaces conducive to design reviews and strategic discussions.

• Operations Tools & Technology: Access to industry-standard design software (Figma), project management tools, and analytics platforms will be essential for effective workflow.

• Operations Team Interaction: Regular opportunities for direct interaction with designers, product managers, marketers, and leadership to foster alignment and shared understanding.

Work Schedule:

• Standard full-time hours (approx. 40 hours/week) with flexibility afforded by the hybrid arrangement. The focus is on output and impact rather than strict adherence to hours, common in growth-stage tech companies.

📝 Enhancement Note: The hybrid nature requires candidates to be self-motivated and effective communicators remotely, while also being able to contribute positively in an office setting for collaborative sessions.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A brief call with HR or a recruiter to assess basic qualifications, cultural fit, and interest in the role.

• Hiring Manager Interview: A deeper dive with the hiring manager (likely Head of Product/Marketing) to discuss experience, strategic approach, and understanding of content design principles.

• Portfolio Review & Design Challenge: A dedicated session to present your portfolio, walk through key case studies, and potentially tackle a small, relevant design challenge or present a solution to a hypothetical problem. This is where your ability to apply data, UX, and copywriting skills will be assessed.

• Cross-Functional Interviews: Meetings with key collaborators (e.g., a UI/UX designer, a Product Manager) to evaluate teamwork, communication style, and ability to integrate into the existing team dynamics.

• Final Interview/Executive Review: Potentially a final conversation with a senior leader (e.g., CEO, VP of Product) to confirm alignment on vision, strategy, and cultural fit.

Portfolio Review Tips:

• Focus on Impact: For each case study, clearly articulate the business problem, your specific role and contribution, the user problem, your design/content solution, and the quantifiable results achieved. Use metrics like conversion rate increases, reduction in support tickets, or improvements in user comprehension.

• Showcase Process: Go beyond the final deliverable. Explain your thought process, how you used data, your iteration cycles, and how you collaborated with others. This demonstrates your strategic thinking.

• Tailor to Sidekick: Research Sidekick's products, website, and app. Highlight portfolio pieces that demonstrate experience in similar industries or with similar challenges (e.g., complex product education, e-commerce CRO, health & wellness).

• Clarity and Conciseness: Ensure your portfolio is well-organized, easy to navigate, and that your explanations are clear and to the point. Avoid jargon where possible, or explain it clearly.

• Wireframing & Copywriting: Ensure your portfolio prominently features examples of both wireframing/UX design and educational copywriting, showcasing your dual capability.

Challenge Preparation:

• Understand the Product: Thoroughly research Sidekick's products, target audience, and current educational content.

• Identify Pain Points: Think about potential areas where users might struggle with understanding Sidekick's products or their benefits, and brainstorm content solutions.

• Structure Your Response: If given a hypothetical challenge, outline your approach: define the problem, identify key user needs, propose content/design solutions, explain how you'd measure success, and discuss potential risks or trade-offs.

• Emphasize Simplification: Practice explaining complex ideas simply, as this is a core requirement of the role.

📝 Enhancement Note: The interview process will heavily scrutinize the candidate's ability to translate strategy into tangible design and copy, with a strong emphasis on measurable results and collaborative potential. The portfolio is the primary tool for demonstrating this.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: Essential for wireframing, prototyping, and collaborative design. Proficiency is explicitly required.

• Design & Prototyping Tools: Experience with other similar tools (e.g., Sketch, Adobe XD) is valuable, but Figma is the stated requirement.

• Project Management Software: Tools like Asana, Jira, Trello, or Monday.com for managing tasks, workflows, and collaboration.

• Collaboration Platforms: Slack, Microsoft Teams for daily communication and team coordination.

Analytics & Reporting:

• Google Analytics: For understanding website traffic, user behavior, and conversion funnels.

• Amplitude / Mixpanel: Product analytics tools for in-app user behavior tracking and feature adoption analysis.

• A/B Testing Tools: Optimizely, VWO, or Google Optimize for running experiments on content and design variations.

• Data Visualization Tools: Tableau, Power BI, or Looker for creating dashboards and reports to communicate insights.

CRM & Automation:

• CRM System (e.g., HubSpot, Salesforce): Understanding how content impacts lead generation and customer data within a CRM context.

• Email Marketing Platforms (e.g., Klaviyo, Mailchimp): Experience in designing and optimizing educational content within email flows.

• Content Management Systems (CMS): Familiarity with web content management systems for website content implementation.

📝 Enhancement Note: The technology stack emphasizes tools for design, analytics, and collaboration, reflecting the role's focus on data-informed UX and content strategy. Figma is a non-negotiable requirement.

👥 Team Culture & Values

Operations Values:

• Clarity & Simplicity: A core value is to simplify complex information, making it accessible and understandable for all users. This applies to both content and internal processes.

• User-Centricity: The user's needs and experience are paramount. Decisions are made with the user's journey and understanding as the primary focus.

• Data-Informed Impact: While intuition is valued, decisions are ultimately guided by data and measured by their impact on user behavior and business objectives.

• Ownership & Autonomy: Employees are empowered to take ownership of their areas, drive initiatives, and make decisions with a high degree of autonomy.

• Collaboration & Support: A culture that values teamwork, open communication, and mutual support among colleagues, especially in a hybrid work setting.

Collaboration Style:

• Cross-Functional Integration: Expect a collaborative style where the Content Designer actively partners with Product, Marketing, and Design to ensure a unified user experience and consistent messaging.

• Feedback-Driven: An open environment for providing and receiving constructive feedback on designs, copy, and strategies to foster continuous improvement.

• Knowledge Sharing: A culture that encourages sharing insights, best practices, and learnings across teams to elevate the collective understanding and execution.

📝 Enhancement Note: The company values seem to align well with a senior role that requires strategic thinking, data literacy, user empathy, and the ability to drive initiatives independently within a supportive team structure.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing Depth and Simplicity: The primary challenge will be to provide comprehensive educational content that addresses complex physiotherapy concepts without overwhelming the user, requiring a delicate balance.

• Measuring Content Impact: Quantifying the direct impact of educational content on conversion rates, user understanding, and product success can be complex, requiring sophisticated analytics and A/B testing strategies.

• Cross-Platform Consistency: Ensuring a consistent and coherent educational experience across the website, app, and email requires careful planning and execution, especially as platforms evolve.

• Navigating Rapid Growth: Operating effectively in a fast-paced, high-growth environment means adapting quickly to changing priorities and scaling processes efficiently.

Learning & Development Opportunities:

• Advanced CRO Techniques: Opportunity to deepen expertise in conversion rate optimization through practical application and experimentation in a real-world e-commerce setting.

• Information Architecture Mastery: Further develop skills in structuring complex information ecosystems for large-scale digital products.

• Health-Tech Industry Insights: Gain specialized knowledge within the health and wellness technology sector, understanding its unique content and user needs.

• Strategic Influence: Develop leadership skills by shaping the educational strategy for a growing company and influencing key business decisions.

📝 Enhancement Note: The challenges are inherent to the role of optimizing user education in a product-driven company. The growth opportunities are substantial for a senior individual contributor looking to make a significant impact and deepen their expertise in a growing industry.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you used content design to significantly improve an e-commerce conversion rate. What was your process, and what were the results?" (Focus on your CRO approach, data usage, and quantifiable outcomes.)

• "How would you approach simplifying a complex technical or medical concept for a general audience on a product detail page?" (Demonstrate your copywriting and simplification skills, and your understanding of user comprehension.)

Company & Culture Questions:

• "What interests you about Sidekick's mission and products?" (Show genuine interest in their health and recovery focus.)

• "How do you approach collaborating with UI/UX designers and Product Managers when your visions differ?" (Emphasize your communication, negotiation, and collaborative problem-solving skills.)

Portfolio Presentation Strategy:

• Structure Your Narrative: For each case study, clearly outline the problem, your role, your solution, and the resulting impact. Use the STAR method (Situation, Task, Action, Result).

• Highlight Data & Metrics: Be ready to discuss the specific data points you used and the metrics that demonstrate success. Quantify your impact whenever possible.

• Showcase Your Process: Explain your wireframing, content creation, and iteration process. Demonstrate your strategic thinking and problem-solving approach.

• Demonstrate Simplification: Be prepared to verbally walk through how you simplified complex ideas in your examples, and perhaps even offer a quick example on the spot.

📝 Enhancement Note: Interview preparation should focus on showcasing a blend of strategic thinking, data-driven decision-making, strong UX/content design skills, and excellent communication abilities, all tailored to Sidekick's mission and growth objectives.

📌 Application Steps

To apply for this Senior Content Designer position:

• Submit your application through the provided link on Workable.

• Tailor your Resume: Highlight experience in e-commerce conversion rate optimization, UX/UI design, information architecture, and educational copywriting. Use keywords from the job description.

• Curate Your Portfolio: Select 2-3 strong case studies that best demonstrate your ability to improve conversion through content and UX, focusing on quantifiable results and your strategic process. Ensure it includes examples of wireframing, design, and educational copywriting.

• Prepare Your Narrative: Practice articulating your experience, process, and impact for each portfolio piece. Be ready to discuss your approach to simplification and user education.

• Research Sidekick: Understand their products, target audience, and current educational content. Prepare thoughtful questions about their strategy and challenges.

⚠️ 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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