My impression is, so far, the longterm strategies of WotC have been focusing on corporate branding, and licensing their IP (intellectual property) of D&D.
This IP promotion led to the production of the Honor Among Thieves, which is a good D&D movie. There are other shows in the works as well. These expand the mainstream recognizability of the D&D game and its many features.
Sometimes the focus on IP interferes with other aspect of the D&D game, especially the attempt to destroy the OGL (open gaming license) recently. But also the IP interference shows up in game design itself, such as pressuring the use of IP, for example the WotC-owned "gods", rather than allowing the Cleric player to decide the "sacred" character concept. In this sense, the IP focus even lacks reallife cultural sensitivity.
WotC decisively ended its tone-deaf assault against the OGL. In hindsight, at least influencial deciders within the corporation better appreciate the practical benefits of promoting the OGL, for a "rising tide lifts all boats" business strategy. At its time, the innovation of OGL was a paradigm shift, a social experiment. But its wisdom proved itself.
As far as I can tell, the DMs Guild turns out to be successful. It too started as an innovative experiment. Generally, the OGL (or now also the CC) allows D&D players to invent and sell products for the D&D game, with access to most of the core rules for D&D, as long as they stay away from proprietary IP that the OGL cannot access. But if selling the independent products thru the Guild, they can even create products using the proprietary IP. The DMs Guild steers which items of the IP become available, depending on which official products WotC wants to promote − which indies can enhance. Then the indy products sold thru the Guild gain a profit for both the indy creator and the WotC corporation. There is a goodwill feeling that this approach is "fair" and smart.
The Guild has a bewildering variety of indy products, of various quality. Some of them are very high quality, such as products for official D&D settings by the inventors themselves of those settings. Even then, it is difficult to decide where to begin when wanting to peruse and purchase a product.
There are plans for DnDBeyond, the official digital venue for D&D, to make it easier to incorporate gaming data from the indy products, including those in the Guild.
These plans to make indy products more accessible promotes the OGL. It also benefits D&D players generally, when they can find more products to meet niche needs. Famously, D&D 5e designers only create "popular" content with high percentage of the approval rating, that appeal to the public generally. Of course this is a good business strategy for selling products. But this approach of the "lowest common denominator" can leave unmet the various specific niche needs that most D&D players have. When the indy products meet these needs, it helps many players to commit to the D&D game engine, because they can find a way for it to do what they need it to do. Of course, the difficulty is to find these products.
I expect future WotC plans to figure out how to navigate and utilize DMs Guild products and other 5e indy products via DnDBeyond. Likewise, to use DnDBeyond to purchase physical products for use at a physical table top.
