Enterprise SaaS is brutal because of cashflow. A16Z even wrote an article on this 9-years ago. https://a16z.com/2014/05/13/understanding-saas-why-the-pundits-

Enterprise SaaS is brutal because of cashflow. A16Z even wrote an article on this 9-years ago. https://a16z.com/2014/05/13/understanding-saas-why-the-pundits-have-it-wrong/ https://a16z.com/2014/05/13/understanding-saas-why-the-pundi... Essentially, in Enterprise Sales - you have huge upfront costs to win a deal (e.g. paying commissions, pre-sales expenses like T&E, marketing, etc). And in SaaS, you only collect a small monthly fee (as opposed to On-Prem when you collected a large upfront fee all at once). So it becomes a cashflow / revenue recognition issue for these SaaS companies and you might not even be profitable until 2-years into the life of the customer contract all due to this cashflow issue. This gets compounded if you're having high growth in New sales (you go further into debt). To this point, when the market crashed in 2008 and sales slowed - that was the year that Salesforce experienced higher than normal profits.