If your subscription uses a freemium model, it can be tricky to decide what’s always free, what’s free for a while, and what’s always behind the paywall. Knowing how to manage people at each stage of the funnel can be really challenging.

Today’s guest, Ken Houseman, is an expert on both the strategy and the technology required to monetize the funnel for acquisition, upsell, and retention. Today’s conversation isn’t based purely on Ken’s work as VP of Product for The New York Times, and in no way represents the editorial perspective of the organization. Ken’s experience there, as well as his work with organizations, including Oracle, Nike, and even the US military, have shaped his perspective on managing the customer relationship.

In this conversation, we discuss why retention is the next obsession for subscription leaders, what needs to be different about how to optimize your ERP for subscriptions, and a few of the less obvious things that can go wrong on the path to conversion.

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