GuerillaBox | Upgrade Pop Up
Background
GuerillaBox is a new service that centralizes a person’s or business’s communication channels with their customers. This includes SMS, emails, WhatsApp messages, Intercom on-site messages, Facebook/Instagram messenger, and more, all in one place. Each channel is referred to as a box; hence, GuerillaBox.
GuerillaBox’s voice is that of an experienced and compassionate business partner. It uses a conversational voice and plays with language to bring joy to the workplace.
GuerillaBox gives users up to three boxes on the free plan. When a user on the free plan has three boxes in use and tries to add a fourth, they encounter a pop-up/error message explaining that they’ve used all of their boxes on the free plan. This is a high-intent, emotionally sensitive interaction.
Ask
Write and design a pop-up error message that explains the situation to the user.
Clearly explain the limitation
Encourage upgrading without pressure
Highlight premium pricing and free trial
Remind users of all available options
Solution
Clearly acknowledged the user’s goal and frustration
Framed upgrading as unlocking flexibility, not removing access
Presented all options transparently (upgrade, trial, manage boxes)
Maintained a supportive, brand-aligned tone
Used visual hierarchy to guide attention to the primary action
Result
A conversion-friendly upgrade prompt that balances disappointment, clarity, and choice.
