There are two men named Issachar mentioned in the Bible. The famous Issachar is Jacob's ninth son;Leah's fifth (Genesis 30:18). The lesser known is the seventh son of Obed-edom (1 Chronicles 26:5).
The name Issachar consists of two parts:
The first part of the name is disputed. NOBS Study Bible Name List suggests a root in the word (ish) meaning man in the sense of a function (man of such and such). This word is written with an aleph, which does not occur in the name.
BDB Theological Dictionary and Jones' Dictionary of Old Testament Proper Names see more in the word (yesh), meaning existence, there is, are. Note that both words are written with a while the first name segment is contains a .
But at least there is agreement about the second part of the name. It comes from the verb (sakar) hire, wages. This verb is used for all the expectable transactions in which someone hires the services of someone else or a group of people (2 Samuel 10:6, Isaiah 46:6, Ezra 4:5).
The birth of the famous Issachar was preceded by the birth and painfully naming of Gad, the son of Jacob with Leah's maid Zilpah (Genesis 30:11). Desiring Jacob's attention and appreciation, Leah had given her maid to Jacob. Now she even purchased the right to sleep with her husband by giving rivalling Rachel the mandrakes Reuben had found in the field (Genesis 30:14-16). Naming her son after the price she had to pay to rent her husband from his other wife shows the same kind of heartbreak Leah showed in naming Gad.
NOBS Study Bible Name List reads Man Of Hire. Jones' Dictionary of Old Testament Proper Names reads He Is Wages. BDB Theological Dictionary favors There Is Recompense.
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(ish) meaning man in the sense of a function (man of such and such). This word is written with an aleph, which does not occur in the name. 
(yesh), meaning existence, there is, are. Note that both words are written with a 
while the first name segment is contains a 
.
(sakar) hire, wages. This verb is used for all the expectable transactions in which someone hires the services of someone else or a group of people (2 Samuel 10:6, Isaiah 46:6, Ezra 4:5). 
