Circupool Edge 40

The cable from the SWG is the same one in this post CircuPool Edge-40 Wiring Help
His second picture, the cable on the right side going into the timer. The black plastic coating/sleeve is not the same diameter as 1/2 conduit or Liquidtite flex conduit like that fitting Rancho posted is designed for. I should be home in a couple hours.
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This bit right ?

Yes - thats what that connector is designed for. The cord goes through the little rubber grommet, and then sits into the little teeth. When you tighten the end-nut, it pushes the grommet into the middle while forcing the teeth to compress in, squeezing the grommet against the cable, producing a water-tight seal.

The cord on my RJ60 is just over 1/4" in diameter (probably 0.300) - the clamp shown above is good for 0.100" - 0.360".

EDIT : To clarify, yes, you'd probably need to drill out any existing hole to accommodate the left-side of the connector - assuming the box doesn't have a standard knock-out for 1/2"-trade fittings already.

Steve