If a CEO sent me a $500k software proposal tomorrow, this is what I would review
If a CEO sent me a $500k software proposal tomorrow, this is what I would review, in order.
The problem statement, before the solution. What does the business lose today, in dollars and months, because this does not exist? If the proposal opens with the product, I go looking for that number elsewhere, and if it is not anywhere, that is the first finding.
The assumptions. Every estimate rests on them: data is clean, the ERP has an API, users will adopt, scope will hold. I list each one and ask what the price becomes when it is wrong. Usually two of them carry half the risk.
The integrations. Named systems, named owners, and whether anyone has confirmed the connection is possible today rather than "planned."
The people. Who owns this inside the company after go-live. A name. If the answer is a department, the answer is nobody.
The exit. Who owns the code and the data, what leaving costs, and what the vendor owes at termination.
The alternatives. What the proposal says about buying instead of building, changing the process instead of either, or doing nothing. If it does not mention them, the vendor decided them on the CEO's behalf.
Then the number. $500k is neither high nor low until the six items above have been read. It is just the last thing on the page, and it is the only thing most people look at first.