Here's a great book I reccomend: "Enterprise Architecture as Strategy" (https://www.amazon.com/Enterprise-Architecture-Strategy-Foundation-Execution/dp/15913983

Here's a great book I reccomend: "Enterprise Architecture as Strategy" (https://www.amazon.com/Enterprise-Architecture-Strategy-Foundation-Execution/dp/1591398398 https://www.amazon.com/Enterprise-Architecture-Strategy-Foun...) As you think about your organizations business processes, and capabilities (note capabilities are distinct from tools, I don't think programmers think about this a lot, but it's important) there are trade offs depending on your business model. The book gives a solid foundation on the trade offs of integrating systems, and not integrating systems. It was written before the modern age of SaaS, and it comes from the perspective of a large enterprise, but the concepts are easily transferrable, and I think you can take some of the ideas and apply it to any company trying to make a build/buy decision.