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Scaling Up the Smart Way: Mastering the Fine Art of Upgrade Prompts for Your Brand’s Success

Jeremy M Williams
4 min readJun 28, 2023

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Alright, we’re getting down to business. In this fast-paced digital world, your UI and UX aren’t just trimmings — they’re the steak and potatoes of your enterprise. When it comes to SaaS or any online product, the key to unlocking a river of revenue is getting users to upgrade. But let’s be clear — it’s not about shoving an aggressive “Upgrade Now!” button in their face. No, it’s about sculpting an experience so compelling that upgrading feels like the only logical next move.

Take a gander at Bitly. They play it smart. The more you lean on their link-shortening service, the clearer the boundaries of the free version become. But they’ve got a secret weapon in the form of a subtle, ever-present upgrade option tucked in the sidebar. It’s a gentle nudge — a constant whisper of the unlimited possibilities just a few dollars a month can unlock. They’ve woven it into their workflow. You can’t ignore it.

Then there’s Async, marching to the beat of a different drum. Their strategy is all about showcasing value. As you immerse yourself in their platform, you start to feel the sting of what you’re missing…

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Jeremy M Williams
Jeremy M Williams

Written by Jeremy M Williams

Empire Builder with a poetic mind. A “Luxury brand expert” with hard knocks life experience. A “Writer” who codes. A “Strategist” who designs.

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