Senior Creative Strategist

Senior Creative Strategist

Sidekick · Canada (Remote) · Full-time · Posted 2026-08-13

Workplace: remote

Description

About Sidekick

At Sidekick, we help people recover faster from injuries. Trusted by Olympic champions and everyday athletes, our products have been featured in Men's Health and Running Magazine. With 94% of users finding relief, we aim to be the go-to injury relief brand.

The role

A lot of performance creative work goes into creating demand that wasn't there. That's not the problem here. Our customer already wants what we sell. Their heel hurts every morning when they get out of bed, or their ankle rolls on uneven ground and they've stopped trusting it.

What they don't believe is that this is the thing that finally works. They've already bought the insoles, done the stretches, and gone to physio twice. So you have to teach before you can sell, and you have to earn trust from someone who has been let down already. It's a harder brief than most, and a more interesting one.

You'll write our paid social advertising and own angle development and testing, reporting to our Creative Director. Expect to ship around 15 briefs a week, a mix of net-new concepts and iterations on ads that are already working. Your week is writing, research, and feedback to editors.

You don't need a physiotherapy background, but you do need to pick up a clinical concept quickly enough to explain it clearly and honestly in fifteen seconds of camera time.

What you'll do

• Find new winning angles. Better creative is what lets us spend more, so we need a steady supply of ads that keep working as budgets grow.
• Open new audiences. Runners, older adults worried about falling, people on their feet all day. Each group buys for a different reason, and every one we crack opens up new demand.
• Get more life out of winners. Read the data weekly, iterate what's working, retire what's finished.
• Write the scripts. Short and long-form video, hooks that stop the scroll, dialogue that sounds like a real person. This is most of your week.
• Direct the edit. Brief and manage editors and creators so the idea survives production.
• Extend what wins. Take proven angles into landing pages and email.

Requirements

What we're looking for

• 4+ years writing paid social ads that were judged on sales (not brand awareness, engagement etc.)
• Your ads have been responsible for over $100K+/month in ad spend (across all your ads, for a single brand). We'll ask you to walk us through it.
• Proof you can iterate on a winner. Plenty of people can write one good ad; we want someone who gets eight more out of it.
• You've opened a new audience before, and you can name the angle that got you in
• Excellent writing for spoken word, which is a different skill from writing for the page
• Strong direct response fundamentals: offer, mechanism, objection handling, proof
• Experience briefing editors or creators
• Health, fitness or medical device categories are a plus

What we care about

We want people who are ambitious and hold themselves to a high standard. They don't need to be managed closely, and want to be the best at their craft. The volume is real and the feedback is direct. In exchange you'll see more results in a year than most people see in three. If you're looking for something comfortable, this won't be the right fit for you.

Benefits

• Compensation: Top of the market for this role. We’ll share compensation details on the first call.

• Fast-growing company whose mission is to solve chronic pain and injuries

• You’ll see the direct impact of your work on business results
• You’ll be held to a high bar, which means you’ll get better fast
• Fun, approachable yet ambitious colleagues
• Comprehensive health benefits
• Preference will be given to candidates in Toronto/GTA. They will be hybrid (2 days in-office, 3 days WFH for). Outside of Toronto candidates will be fully remote

Apply

Apply at Sidekick

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