The Freemium Email Challenge

Freemium SaaS has more users than most business models but fewer of them pay. Your email strategy needs to serve two purposes: keep free users engaged (so they eventually convert) and convert the right users at the right time (when they experience the need for paid features).

The worst thing you can do is blast your entire free base with generic upgrade emails. The best thing you can do is trigger upgrade conversations when individual users hit the moments where paid features would genuinely help them.

Usage-Based Triggers Beat Time-Based Drips

A freemium user who hits their storage limit on day 3 needs an upgrade email on day 3, not day 14. A user who has been on the free plan for 6 months without hitting any limits probably does not need upgrade pressure at all.

Usage-based email triggers align your communication with the user's actual experience. They feel helpful instead of pushy because they arrive when the user is experiencing a real limitation.

The Pricing Problem

Per-contact email pricing is a trap for freemium SaaS. At 50,000 free users, per-contact tools charge you for 50,000 profiles even though 95% of them are not generating revenue. Pay-per-email tools only charge when you actually send, which means your email costs scale with your actual communication, not your total user base.

Factor this into your tool choice early. Migrating email platforms later is painful and the pricing difference compounds as your free base grows.