Senior Content Designer

2 weeks ago

Toronto, Ontario, Canada Sidekick Full time

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 Senior Content Designer to own how educational content is structured, presented, and delivered across Sidekick's website and app.

Your job is to ensure customers get the right information, at the right time, in the right format — so they feel confident buying and are successful using our products, without feeling overwhelmed.

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

What You'll Own
  • Education Across the Customer Journey: Envision and own how product education is delivered across PDPs, landing pages, email flows, and the app so customers get the right information at the right time
  • Where Users Get Stuck: Identify where customers feel confused, hesitant, or unsure — and fix it
  • Design & Wireframing: Translate your vision into wireframes and work with designers to bring them to life
  • Educational Copy: Write and refine high-impact educational copy that translates complex physio concepts into clear, human explanations
  • Content Simplification: Continuously simplify or remove content that adds friction or overwhelms users, even if it feels "important"
What Success Looks Like
  • 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

Requirements

  • 7+ years of experience improving ecommerce conversion through CRO and UX decisions
  • 7+ years of UX/UI experience with strong instincts for information architecture and user flow
  • Proven ability to design or wireframe ideas yourself and work closely with designers
  • Data-informed but not data-blind — you balance metrics with judgment
  • Clear communicator who simplifies instead of over-explaining
  • Strong design skills (Figma or similar)
  • Strong copywriting instincts, especially for educational content

Benefits

  • Competitive compensation + performance-based bonus
  • Comprehensive health benefits
  • 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

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