I've had to replace 2-3 starter pinion gears on V twin Vanguards. When the gears went bad, they made more of a grinding sound than the noise yours makes so I have no idea what is wrong there.
Briggs uses both metal and plastic starter gears. Your 1440 should have a plastic gear. DON'T try to use a steel gear in place of plastic, shelled teeth on the flywheel will be the result.
You'll also find it very handy to have a 10 mm wiggly socket to use on the top starter mounting bolt. I got one from Sears and shortened the hex head just short enough to capture the head of the bolt. The shorter the socket, the better.
While you have the starter out, that would be a good time to clean up the brushes and commutator and lube up the armature bushings in each end. Also, check the flywheel end of the armature bushing for wear. Some get bad enough to cause the teeth to get knocked off the starter gears.
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