I had done a similar career. Started unemployed, and after being approached by a number of Serie B teams, Siena offered for me in November, they were last by about 15 points. Signed a couple of Juve players on loan in the Jan transfer window, but alas couldn't save them, and got relegated by 5 points. I had had an incositent season, with my strikers permoring great one game (Maccarone scoring 4 goals against Roma[who were 4th] when i won 5-3), then not being able to score one goal against anther relegation candidate. I had asked for a 7 month contract since i wasn't sure i'd be able to save them, and left in the summer of 2010.
Was unemployed till November again, this time West Ham came for me, and when i joined they were 19th in the league. With a few shrewd signings in January including Ekdal, Molinaro, Benayoun and Kirklind, i took them up to 9th. The following season i brought in a couple of other players such as Maxi Rodriguez(who was listed at Utd), and started well, till December was in a Europa League spot. Then i received a 20 million offer for Diamanti and sold him, since he was not doing too well for me, and after that went on a losing streak of about 6 games, and dropped down to 12th. Board were not very happy with me. Liverpool sacked Benitez at the same time, offered me the job and took it. End of that season i finished 8th (they were 15th when i joined). First full season in charge i bought a few players, such as Lukaku, Dzeko, Badstuber, Di Maria and Joe Hart. Finished the season in 4th. Second season in charge brought a few more new faces like Diego and Gignax. Finished second, and got knocked out in the quarter final of the champions league. Current season is only 3-4 games old, but am currently drawn first with Tottenham