Pilot official history page in Japanese says their company name means a maritime pilot. That's why their company symbol depicts a lifesaver.

According to
Japanese Wiki on Pilot Corporation, the founder of Pilot, Ryosuke Namiki, graduated from and taught at Tokyo Merchant Marine Academy (current
Tokyo University of Marine Science and Technology). He was once a crew of a merchant ship, too. He used to use drawing pens while aboard, but did not like those pens and developed a pen that was more convenient (unfortunately the site does not elaborate on what kind of pen it was). He named his pen "Pilot Pen" and asked his wealthy former classmate Masao Wada to invest in the company and they founded Namiki Seisakusho together.
The official site also says that they are the leader of the big group of ships

Therefore they are ahead of sailors, I guess

While I was searching Ryosuke Namiki, I found
this Taiwanese blog...the author has visited Pilot Pen Station, and took a lot of photos. About half way down there are portraits of Wada (on the left, gray hair) and Namiki (on the right, dark hair). Very nice blog! Woody, do they have the original Pilot pen at Pen Station?
EDIT: Added some links.