Suppose in a small technology company, Paul Smith, the CEO, also acts as VP of Engineering. Both the management team and all of the programmers report to him. So, how do you show this?
Instead of engaging in exotic formatting, it's best to draw both positions in the chart and show Paul as occupying both of them. Remember the organizational structure is based on positions, not the people that occupy them. Following this simple guideline will give you a more functional org chart.
This also shows how an org chart can be useful for planning. This one suggests that perhaps, some day, Paul should hire a VP of Engineering.