He did say he has 20' of head, but he may be misunderstanding head (aperantly i am too). I thought you just measure the amount of linear feet you have from the skimmer to pump + drain to pump.... something along those lines.
There are two types of head, static and dynamic.
If you pump water from a lower level to a higher level, that is static head. For most pools, static head is zero because the water returns to the same level it came from. However, if you pump from a lower pool to a higher pool, the difference in elevation is the feet of static head.
Dynamic head is the amount of pressure required to move water through the system (pipes etc.) due to friction with the system components (pipe walls etc.). The amount of pressure needed depends on water flow rate, pipe diameter, pipe material, fittings, length of pipe and anything that restricts water flow. The pressure needed can be measured in feet of head, PSI or other pressure measurements.
Total head is the sum of static and dynamic head.
Length of pipe is just one factor that determines the amount of dynamic head.
You could have a 1,000 foot pipe and a 100 foot pipe moving the same GPM and have the same feet of head (head loss) if the pipes were sized correctly.
For example, if you had 100 GPM moving through 100 feet of 2” schedule 40 PVC, you would have a head loss of about 16.5 feet.
To move 100 GPM through 1,000 feet of pipe at the same head loss, you would have to increase the pipe inside diameter to about 3.32 inches.
Moving 100 gpm through 100' of 2" pipe or 100 gpm through 1,000' of 3.32" pipe creates the same head loss as pumping from one pool to another pool that was 16.5' above the first pool.
To measure total feet of head, you can put a pressure gauge immediately before the pump and immediately after the pump while the pump is running and the difference in pressure is the total feet of head. You can convert gauge measurements units to feet of head. For example, 1 psi is equal to 2.31 feet of head.