The hard part is making hundreds of decisions that won't quietly compound into outages, cost blowouts, security gaps, or organizational gridlock. That's why, even when organizations are moving from cloud to cloud or swapping one set of managed services for another, they still need deep planning capabilities.
Most successful SaaS companies begin with strong intuition. Founders understand the problem deeply. Early decisions are fast, informal, and often correct. The closeness between insight and action creates momentum that is hard to replicate later. As companies grow, that intuition becomes harder to rely on. Teams expand, customers diversify, and systems become more complex. Decisions that once felt obvious now feel risky. Many organisations respond by pushing harder on the same instincts that drove early success. Rupon Anandanadarajah has seen where that leads.
"Here we go again, I thought", as I listened to the board member tell me how frustrated he was with the founder of one of their venture firm's most promising investments. Sadly, I knew the call was likely too late to prevent an inevitable cascade of emotional and financial consequences. Working as an executive coach in Silicon Valley with venture capital firms and the companies where they have placed their investments means being at the confluence of high-stakes financial and career risk.