Ken Houseman

You want to remind users what they’ll be losing if they cancel their plan, but it should be easy to find, and you don’t want to prevent users from canceling. You want to understand why they’re leaving and see if it can be fixed (e.g., if it’s the price, you can offer a discount).

AI is a tool, like spreadsheets, so you don’t set it and forget it. The pricing model may not change, but the environment changes, and there can be slight differences in attributes (e.g., age, gender identity, people who moved, etc.). When you find behaviors that are not meeting your experiment expectations, you have to deep-dive so you can retrain the models and target users differently.

Abandon cart communications is the way to tackle helping consumers finish transactions, and it’s super important. But if that’s all you’re doing, it’s not enough: you should be obsessing about customers not abandoning the cart in the first place.

If a user is interested in one product, The NY Times wants it to be the best product for them and have it priced for them. But if a user is interested in that product and one other thing, they’d rather upsell the user from that one product to the bundle. The subscriber then uses one product the most and then sometimes the other one—products at The NY Times: Journalism, Games, Cooking, WireCutter, etc.

Pricing right is all about understanding each user’s behavior so you know when it’s the right time to put a paywall in front of them. It’s figuring out what they are ready for and then displaying the corresponding offer. If users don’t take advantage of an offer, it feeds back the model to better serve the right offer later (at the right time and price).

One of the fastest ways to lose a subscriber is to price them out. When you’re thinking about your upgrades to bundles and cross-sells, make sure you have a price point that entices them to get in and matches the value at that time in their lifecycle. Example: The NY Times has a $1/week offer, then over time, as they understand users’ behavior, they step you up while providing more value.

When it comes to privacy and regulations, the worst thing you can do is get entrenched in the path/roadmap/strategy you have because this will create a blind spot. It might be best to pause your efforts and address a change before it becomes a problem.

When it comes to privacy and regulations, the worst thing you can do is get entrenched in your path/roadmap/strategy because this will create a blind spot. It might be best to pause your efforts and address a change before it becomes a problem.

You have to be voracious about seeking out what’s coming down the pipe regarding privacy and consumer protection. You have to stay on top of national/state and international laws to understand which things are most likely to hit you and have the flexibility to pivot. For example, cancellation flow rules now stipulate you give equal ease to cancel online than to subscribe.

Don’t underestimate the need for quality data, whether with a partner or a system you build internally. You have to understand the behavior of your subscribers and measure the impact on your core KPIs of anything new you introduce or experiment with.

Retention is the next-step session. It’s about making sure you constantly find those natural connections with your subscribers for whatever matters to them in your product. Example: serving a weekend baker who saves weekly recipes vs. a hyper-political news consumer.