This quest starts after the player agrees to do a favor for Sha'khar after accepting the previous quest. (This quest and the previous can be done in tandem.)
Sha'khar will ask the player to head to the docks near Solitude and speak to his business partner Korrin; the player will receive an objective to do so.
Korrin will inform the player of a plan to convince the Jarls of Skyrim to give the East Empire Company their blessing to operate within their holds. The player's first target is Winterhold.
Korrin will give the player a book they can use to bribe the Jarl, as well as an East Empire Ring to identify the player as a representative of the East Empire Company. This ring grants a bonus to Barter prices.
In Winterhold, if the player is wearing the East Empire Ring, a character with the label "Shady Contact" will approach the player and offer them an alternative solution to convincing the Jarl to allow the East Empire Company to operate there.
See East Empire Blessings: Winterhold page for details on convincing the Jarl.
After the player convinces the Jarl to allow the East Empire Company to operate in Winterhold, they'll be given the objective to return to Korrin.
Korrin will congratulate the player and tell them to continue convincing Jarls. He'll also remind the player they need to get the blessing for Whiterun as well.
If the player has not yet completed the base game quest "Rise in the East", they will receive a miscellaneous objective to speak to Orthus Endario.
The quest will then complete.
At this point, the questline remains dormant until the player has convinced enough Jarls, and engaged enough in the East Empire services. See the next quest's page for specifics.
At this point, if the player returns to Winterhold, they will find a new East Empire Outpost established in an abandoned building near the bridge to the college.
Any time the player goes to any East Empire Outpost, Sha'khar will greet them and tell them of any new services they've unlocked.