Titus was no stranger to conflict. He was a long-term companion of Paul who was a valuable aid in two of Paul's greatest crises.
Titus first appears in the New Testament in Galatians 2:1, where Paul says he took Titus along on his trip to Jerusalem with Barnabas. Titus was a Gentile, and the issue at hand was whether Gentiles should have to comply with Jewish ceremonial rites (circumcision, diet restrictions and so on) in order to be full members of the Christian community. With the young Paul at one side and Barnabas at the other, he was essentially "tried" (and acquitted) by the leaders in Jerusalem.
Titus appears again in the middle of Paul's struggle with the church at Corinth. In that deeply divided church, he represented Paul. He had the unwelcome job of delivering what we call the "severe letter" which Paul refers to in 2 Corinthians 2:1-4 and 7:5-13 and then staying there for about a year. Then he delivered the letter we now call 2 Corinthians in which Paul takes on his critics and calls the church to honor an unfulfilled financial pledge.
Titus was in Crete at the time Paul wrote him. Crete was a seaport, a sleazy port of call for cargo ships traversing the Mediterranean. It had been socially backward for 1400 years when the Minoan civilization was destroyed by a devastating earthquake. We do not know exactly when Titus went with Paul to Crete, but one possible scenario places it after Paul's release from his first imprisonment in Rome.
Paul had preached in Crete and was giving Titus the job of following through with developing a healthy church. This letter was sent while he was in the midst of his task and reviews his assignment. It shows Titus as a forceful personality and skilled administrator. It seems he was made of tougher stuff than Timothy, but his assignments were shorter. By the time Paul had written 2 Timothy, the job in Crete was done, and Titus had been sent on to Dalmatia (part of modern Yugoslavia).
This letter gives us two very valuable things: (1) A showcase of Paul's strategy for leadership in the midst of chaos—Timothy was given a long-term assignment in an established church; Titus was sent to follow up an evangelistic movement and give the Christian body some coherence; (2) a model of hope in the face of a very messy situation; Paul's confidence in the power of the gospel shines throughout the letter.