Inspired by a recent blog post and the hilarious job application for Chess.com CEO, I decided I would actually think seriously about what the game plan would be: my three main focus areas in my first year.
I’ll start with background. I certainly don’t have years of experience in management or running a budget. I’m somewhat senior, but I’m an IC (data science). So I don’t meet the requirements of really being a CEO. I do have some experience at companies not unrelated to the Chessable business. But in the words of every person whose job you don’t really understand and in fact believe is plausibly more of a make-work situation for the child of the royal family of some small, obscure country: for this post, “I am really an ideas guy.”
Scalability up — and down. Clearly, there are architecture issues we need to solve. Chess.com was — not so long ago — a much smaller website with much less traffic. At the same time, we are not a large company and we shouldn’t be. Our demand will fluctuate as chess moves in and out of demand. We need to have an architecture that can rapidly scale up and down to take advantage of opportunities without raising our permanent cost base. My first question to engineering: “What is the lowest cost way to achieve this?”
Content strategy. Do we have a reasonable estimate of the return on our content investments? Show me the numbers and how we got these estimates. This is more my area of “core competency” so I would take a bit of a hands-on approach here. I want to understand where we should be spending. Is our original content (tournament broadcasts) more valuable than streaming contracts — or vice-versa? Being a streamer and showing up on Chess.com is super valuable for the streamer. How valuable is it for us? To show a large set of people playing chess. Or should we double down on our biggest streamers — perhaps, effectively, pushing to make them part of the company to lock them in? The only way to answer these questions is with data. We need a way to score the incremental revenue to Chess.com from these various partnerships. I get the sense that these partnerships have been valuable for driving a lot of the rising interest in Chess in recent years. For us to make effective decisions, we need to know how much of that interest translates into dollars for Chess.com.
The Casual Player’s User Journey. Our subscription product and Chessable courses are fairly expensive, and a play-a-couple-games-every-now-and-then-on-the-toilet player will never subscribe or purchase one of these courses. Many more of our players are in that category than in the chess improver category who is really trying to get better, watches our content, etc. This group of players probably doesn’t even know we do content. They just want to play a fun game for a few minutes. Our current revenue from these players is ads. Ads are great, but what we really need is to drive Casual players down a journey to want to become better and spend on subscriptions and Chessable courses. Here I want to work on improving the product. We could show the coolest tactics that the player missed during the game for free accounts to produce a moment of “wow, that’s cool”. We could then lead to suggesting subscribing to be able to practice puzzles so we don’t miss the tactic next time. I also think casual players who play longer time control games will be more likely to convert to paid products. How can we get the casual blitz player to try rapid? Can we place Rapid more prominently for users that have played significant games? Blitz is probably useful for onboarding. This could be the first part of the journey from casual to fanatic. I see one journey as: casual Blitz → casual Rapid → casual Rapid/Blitz + Puzzle Rush (now, we’re in the money) → improver (chessable money) → Magnus Carlsen.