Senior Content Designer

Base pay range

CA$/yr - CA$/yr

Total Comp: $100k – $120k CAD + performance bonus

Sidekick’s mission is to help people recover faster from persistent injuries. Trusted by Olympic athletes and everyday customers alike, our products are used by hundreds of thousands of people worldwide and have been featured in Men’s Health, Running Magazine, and more.

Our products are inherently education-heavy. Customers have real questions before they buy — how it works, whether it actually helps, how to use it properly, and how it compares to alternatives. When handled poorly, this overwhelms users and hurts conversion. When handled well, it builds trust, clarity, and confidence.

As we scale our website, app, and product ecosystem, how education is delivered has become a core growth lever.

We are hiring a Content & Conversion Manager to own how educational content is structured, presented, and delivered across Sidekick’s website and app.

This is not a traditional content role
.

This role sits at the intersection of conversion rate optimization, UX/UI, ecommerce, and product education
. Your job is to ensure customers get the right information, at the right time, in the right format — so they feel confident buying and successful using our products, without feeling overwhelmed.

You will envision how education lives across the customer journey and either design/wireframe solutions yourself or work closely with designers to bring them to life.

1. Conversion-Focused Education Strategy

• Own how product education is delivered across PDPs, landing pages, quizzes, modals, onboarding flows, and the app
• Decide what information is shown, when, and how (pre-purchase vs post-purchase)
• Ensure education feels clear, lightweight, and confidence-building — not like reading a textbook
• Design progressive disclosure systems (accordions, tabs, tooltips, modals, step-based flows)
• Structure information so it’s easy to scan, digest, and act on
• Reduce cognitive load and decision friction using strong UX principles
• Create consistent education patterns across products and platforms
• Identify where unanswered questions block conversion
• Partner with marketing and product teams to test education formats, placements, and messaging
• Use data, user feedback, session recordings, and intuition to guide improvements
• Remove or simplify content that hurts conversion, even if it feels “important”

4. Design & Execution

• Create wireframes, flows, or low-fidelity designs for education experiences
• Work with designers to bring concepts to life when needed
• Ensure web and app education experiences feel cohesive and intentional
• Maintain quality and consistency as new products and features launch

5. Copy & Messaging

• Write or refine educational copy where needed
• Translate complex concepts into simple, actionable explanations
• Maintain a clear, confident, human tone — not clinical or academic
• Ensure consistency in language across web, app, and product ecosystem

• 7+ years of CRO experience and improving ecommerce conversion
• 7+ years of UX/UI experience with strong instincts for information architecture and user flow
• 7+ years designing or wire framing ideas yourself and working closely with designers
• Data-informed but not data-blind — you balance metrics with judgment
• Clear communicator who simplifies instead of over-explaining
• Design skills (Figma or similar)
• Strong copywriting instincts

• Customers feel informed and confident without feeling overwhelmed
• Conversion rates improve while education depth increases
• Fewer pre-purchase questions and post-purchase confusion
• Education feels intentional, structured, and easy to digest
• The website and app feel like guided experiences, not content dumps

Sidekick products work best when people quickly understand how to use them and what to expect. Education is essential — but too much information, or information delivered poorly, creates friction.

Customers shouldn’t feel like they need to read a manual before buying. They should feel clear and confident within seconds. This role exists to identify what information matters most and deliver it clearly, intuitively, and often visually, so education helps conversion instead of slowing it down.

As we add more products and expand our app, getting this balance right becomes increasingly important.

• Competitive compensation + performance-based bonus
• High ownership and decision-making autonomy
• Direct collaboration with product, marketing, and leadership
• Opportunity to define how education scales across web and app
• Dedicated, collaborative, and supportive colleagues
• Fast-paced, high-impact environment during a period of rapid growth
• Hybrid role with work-from-home flexibility

Please fill in the form to apply:

All applicants who have not filled in the form will not be considered.