What drives the decision to have product change communications on a monthly cadence vs when the changes go live? Or a hybrid? e.g. "January roundup" vs "Faster search is here 🎉"

I think it depends on your audience, product, and goals. What do you want your audience to really understand about the product you're shipping? Do you want them to perceive that you are constantly shipping new things? Is part of your competitive advantage that you're building product faster than other companies in your space? Is this something your audience even wants, or would they prefer more considered/perfected big launches that meaningfully change their experience with it? 

We like to stick to a monthly cadence unless there's something shipping that we want to call extra attention to because it will have such a major impact on the everyday eperience of using the product. If there are features that you know your audience is going to be very excited about, or that you know will support the type of narrative you want to tell about the company, then you should break those out and give them room to breathe. 

For instance, we knew launching better search was very keenly anticipated by Notion users, so we made that the very clear marquee feature launching, as opposed to burying it with a bunch of other things just for the sake of shipping a neat bundle all at once.

I've worked at companies with different philosophies on this. The main benefit of a monthly or other regular cadence is predictability - i.e., everyone in your organization is aware of launch timelines and can plan accordingly. Customers always know when to expect product comms. But a con is that releases can get lost when they're bundled together and when updates become very regular or templated, they can become less interesting to a customer.

On the flip side, sometimes it's not ideal to wait (or scramble) to push out a product or feature by a certain time every month, and having rolling releases can offer more flexibility. For this reason, many earlier stage companies do rolling releases. From a product comms standpoint, one challenge you might face when doing rolling releases is that timelines constantly shift, and you might be spending more time aligning internally on launches. You also need to be careful about not over-blasting customers with communications. But a pro is that you can drive education and adoption of specific, important features.

A hybrid is a nice blend of both worlds. You have predictability around planning and comms with a monthly cadence, but for major Tier 1/high-customer-impact releases, you can do dedicated comms so they get the airtime they deserve.

I like to have the flexibility to do both. But, if you see it as this or that, the latter ("Faster search is here") is designed to be a delightful surprise, the former (monthly cadence) is more of a type of predictable FYI. These decisions should be driven by lots of different aspects such as your org's overall email / customer comms strategy, feature implementation needs (will the large enterprise admin need 2 months to deploy this feature across their global org?), velocity of features/releases.

In the world of UCaaS, many admins appreciate the heads up around product change communications, especially around things that require implementation.

Ah-ha moment: Most customers (let alone internal employees) cannot keep track of the sheer velocity of updates that come from all the SaaS companies. Think about multi-channel ways to update your customer (without spamming them). In-product messaging & walk-throughs, admin emails, marketing emails, social tips and tricks. We sometime assume that because we sent them an email, customers are now up to date with our latest news. That could not be more wrong in today's world of digital noise.