For freemium products, at what point (in terms of usage or team size, etc.) do you prompt or pressure free users to upgrade, and how do you message that nudging without alienating them?

Below is a summary of the approach recommended in Price to Scale for freemium models regarding when to prompt users to upgrade and how to do it gracefully:

Directly answer the question
• The ideal time to suggest an upgrade is when natural usage thresholds are reached – for example, when a free user or team has outgrown the limitations of the free tier (e.g., growing team size, increased usage, or the need for more advanced features).
• The shift from using a free tier to needing additional functionality should feel like a logical next step rather than a forced step-up.
Insights from our book, Price to Scale
• In our book we note that the freemium model should shape product development so that free users are naturally enticed to upgrade. This means designing the product in a way that premium features gradually provide more value as the user's business scales.
• Our pricing strategy emphasizes creating tiers that allow for a natural and gradual progression rather than pushing upgrades through overt pressure. As we explain, “you can't force people to upgrade. You can only create tiers that allow for natural growth in their business.”
• Instead of abrupt nudges, the messaging should focus on highlighting added value and benefits associated with upgrading without insinuating that the free version is inferior or “limiting” their success.
How to message the upgrade: Practical messaging tips
• Use data-driven insights: For example, if a team has expanded significantly or is using the product heavily, a non-intrusive message can mention that as organizations scale, many find that premium features help manage complexity or unlock further efficiencies.
• Frame the upgrade as an enhancement rather than an interruption: Instead of “pressuring” users to move up tiers, offer clear explanations of what additional capabilities or support they stand to gain (e.g., better collaboration tools or tailored support).
• Be transparent: Clearly inform users when their usage or team size is approaching the limits of the free tier, and provide alternatives like a discounted upgrade or short-term commitment options that can make the transition smoother.
Key takeaway
• The timing should be organically tied to usage metrics and team growth, ensuring that as a user’s needs become more complex, the upgrade feels like a natural solution.
• Messaging should always remain empathetic and solution-based, avoiding any implication of “penalty” for staying on the free plan while promoting the tangible benefits of upgrading.

In summary, our approach in Price to Scale is to let the product’s design and the natural evolution of customer needs guide the upgrade prompt, coupling it with clear, value-based messaging that resonates with users without alienating them.