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Dropbox Hiring Remote GTM Readiness Manager in Canada

Dropbox is looking for a GTM Readiness Manager based remotely in select Canadian locations — a senior cross-functional role bridging product and commercial execution.

DigiNomad Editorial·Oct 15, 2026·1 min read

If you're a remote worker in Canada with a talent for translating complex product decisions into real-world business action, Dropbox has an open role worth checking out. The GTM Readiness Manager position sits inside the company's go-to-market organization and is open to candidates in select Canadian locations.

The role is essentially a connective layer between Dropbox's product teams and everyone responsible for actually taking that product to customers — Sales, Marketing, Customer Success, Finance, Legal, and more. Day-to-day, that means spotting cross-functional dependencies before they become problems, making sure all the moving parts are ready before a launch, and ensuring that both customers and sellers have a smooth experience when something new hits the market.

What makes this one interesting for experienced remote professionals is the breadth of exposure. You'd be touching nearly every part of the business, working on everything from new product releases to packaging changes and broader commercial model shifts. There's also a mandate to help grow the GTM Readiness function itself — so it's not purely execution work, there's a strategic and organizational-design element too.

For Canadian-based digital nomads or remote workers who prefer a structured corporate environment over freelance uncertainty, senior roles like this at established tech companies can offer strong compensation, meaningful scope, and the flexibility of full remote work.

Inspired by reporting from We Work Remotely: Remote jobs in design, programming, marketing and more.