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Dear SaaStr: Our Biggest Customers Are All Asking for Custom Features. When Do We Say Yes?

Jason Lemkin · SaaStr Free Intermediate

This is the exact question you are asking, answered by someone who has sold a lot of enterprise software. Lemkin gives you a usable rule instead of platitudes: say yes when the feature is reusable by other customers and fits your next 24 months of roadmap, charge for it either as a one-time fee or a higher annual price, and cap the share of engineering you spend on any one big deal. It is a starting point for turning a gut call into a repeatable filter.

• Say yes mainly when the requested feature can be sold to other customers and already fits your roughly 24-month roadmap, not because one account is loud or large.
• Price the custom work, either as a one-time fee or baked into a higher annual contract, so bespoke building at least breaks even instead of quietly becoming a cost center.
• Put a ceiling on it: allow only a small slice of engineering (he suggests around 10 percent of story points) for big-deal customization, and do one or two at a time so the roadmap stays yours.