Location: Hybrid

Employment type: Full-Time

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

About Sidekick

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.

About the Role

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.

What You’ll Own

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

2. UX / Information Architecture

Design progressive disclosure systems (accordions, tabs, tooltips, modals, step-based flows)
Structure complex 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

3. CRO & Experimentation

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

Who You Are

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 wireframing 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

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

Why This Role Matters

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.

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

To Apply

Please fill in the form to apply: https://sidekicktool.typeform.com/to/B0QOY3yP

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

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Content & Conversion Manager (CRO, UX/UI, Ecommerce)