He signed a contract with Warner Music Taiwan in 2008 and released his debut album, Jam Hsiao, in the same year.

The show's production unit recognized his talent and wanted him to appear as a challenger in the already unraveling first season.

Hsiao was arranged to be in a player knockout(PK)[further explanation needed] style singing match against the show's 10 best remaining contestants.

His brief appearance on the show captured the attention of the music industry at that time and the restaurant he was singing at was full house whenever there was his shift.

Even though at this time he was not signed with any music record company, Hsiao received many invitation to go on variety shows.

A-Mei is known as Taiwan's Queen of Pop and she invited Hsiao to sing with her in the duet "Moment of the First Sight" (一眼瞬間) in her 2007 music album Star.

In December 2007, Hsiao performed a medley of four nominated original themes in the Golden Horse Award, the most significant event for film industry in Taiwan.

In July 2008, Hsiao's New-song Premiere Concert at Taipei Danshui Fisherman's Wharf Attracted over ten thousand fans.

Although he did not win the title, his extraordinary performance had won him a solid position in Taiwan music industry.

He had a cameo in the popular Taiwanese drama "Fated To Love You／ 命中注定我爱你" and received many positive reviews.

This song was released as an EP with video to raise funds for the Genesis Social Welfare Foundation.

Without dancers or guest singers, Hsiao single-handedly completed his first large-scale concert and earned enthusiastic praise.

[1] In the beginning of 2011, Hsiao was voted as one of the most desirable singers by the audience in China, and was invited to perform in a trio with Li Jian and Khalil Fong on CCTV New Year's Gala.

Although his performance was a disappointment, his attitude, courage and professionalism earned the respect of the production unit, the fellow musicians and the hearts of the audience.

In 2012, Hsiao released his first full English album, consisting of eleven covers of known classics—such as "How Deep Is Your Love" by the Bee Gees and "L-O-V-E" by Nat King Cole—recorded from his Mr. Jazz Private Party Live.

With the album, Hsiao showcased a 180-degree change in style and performance manner—from the powerful Mr. Rock to the soothing Mr. Jazz.

This time, in addition to album producing, songwriting, singing, background vocal arrangement/singing, he also directed an MV for the song "Marry Me".

One of his students, Xiao Yi Hang won first place after three months of competition and was subsequently signed with his record label company, Warner Music Ltd.

The song "Kelly" was chosen as the end track for the Korean drama "You Who Came From The Stars" which was aired in Taiwan in May.

In September 2016, Hsiao formed the band Lion, together with Lee Q Wu, Tsou Chiang and Liu Chao-chu.

In the same year, he appeared as one of the mentors of Zhejiang Television's Sound of My Dream, together with Yu Quan, Hebe Tien, JJ Lin and A-Mei.

[4] In 2010, Jam Hsiao joined the cast of a movie, The Killer Who Never Kills, based on a series of novels by popular Taiwanese novelist Giddens Ko.

Hsiao played the lead role of as the "Master of all Geeks" in his second film, romantic-comedy movie My Geeky Nerdy Buddies, directed by Kevin Chu alongside China artistes Jiang Shuying and Xie Na.

In June 2023, Jam Hsiao announced his engagement to his manager Summer Lin, whom he had secretly dated for 16 years.