At what point should a customer be moved from self-serve plans to a negotiated enterprise deal? (e.g., if they exceed a certain number of users or dollars per year, should we require an enterprise contract instead of letting them just buy online?)

Based on our saas pricing book, Price to Scale, the answer is that there isn’t a single numerical threshold (like a specific number of users or dollars), but rather a signal from the customer's evolving needs and the complexity of their requirements.

Key points from Price to Scale include:

• When customers start asking for more flexible, bundled offerings than what your self-serve plan provides (such as needing enterprise license agreements or a broader range of features), it’s a sign that they’ve outgrown the simple pricing model.
• If the cost structure begins to force a small or medium-sized customer into paying significantly more (for instance, paying 1.5–3 times as much) for features they don’t necessarily need, it creates inefficiencies and can negatively impact customer satisfaction and your net retention rate.
• The self-serve approach works best for transactional, high-velocity sales where customers can quickly sign up and play. Once a customer’s usage or strategic needs shift to require negotiated terms—whether that means volume discounts, customized product bundles, or additional legal and administrative support—the enterprise deal becomes the appropriate format.

In practical terms, you should consider moving a customer from self-serve to a negotiated enterprise contract when:

Their usage or revenue generation substantially exceeds the levels intended for your self-serve model.
They start to require contractual flexibility, such as customizable features or negotiated discounts, which your self-serve tier cannot accommodate without compromising the simplicity and predictability of the plan.
Maintaining them on a self-serve plan would result in either overcomplicating your pricing tiers or providing them with a bundle of features that leads to underutilization (or “shelfware”).

In summary, the decision to shift a customer to an enterprise deal should be less about hitting a strict numerical threshold and more about recognizing when their needs—and the value they extract—demand a more tailored, negotiated solution. As discussed in our pricing strategy book, Price to Scale, aligning your pricing architecture with customer demands ensures both operational efficiency and improved customer satisfaction.