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ChristianKl comments on Effective altruism and political power - Less Wrong Discussion
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In both cases one of the most important skill is hiring the right people and delegating responsibility to them. A person who grew a startup to a massive company is likely better at that skill then the average senator.
The President has to be able to operate effectively within the existing structure and deal with the people who were elected by voters or rose up through the bureaucracy. I don't know that running a successful startup is a good way to get acclimated to overseeing the largest bureaucracy in the country and working within the system to get things done.
In the US the president can pick a lot of the people who work under him. He isn't as limited as UK or German politicians in that regard.
Big tech companies also go through a lot of negotiations. They acquire companies, negotiate deals with other companies and they do lobby for political legislation.
They still aren't Washington insiders. They lack relationships and inside knowledge about how deals get made in Washington. That's not perfect but they can hire people who do know how Washington works.
To the extend that we aren't happy with the way Washington works and want a change in how it operates, having a president who's not a Washington insider has advantages.