In 2008, Jaiveer was accepted into the Chambers of Abhishek Singhvi, who is Senior Advocate, a Rajya Sabha MP, and a spokesman of the Indian National Congress party.

[8] Shergill served as the Young India representative for the International Bar Association, one of the most prestigious lawyer organizations in the world, for a period of two years (2008–09).

[9][failed verification] Jaiveer has also represented one of the two sides in a controversial dispute regarding the offering of prayers at a site claimed by two religious communities in Karnataka state.

[4][13] Jaiveer was instrumental in voicing various economic and social issues in the media including but not limited to foreign direct investment,[14] depleted conditions of schools in Punjab,[15] alarming drug use,[16] women safety[17] etc.

In 2018, Jaiveer was named as one of the 25 Munich Young Leaders to take part in the Munich Security Conference in Germany to discuss international security issues, including the resurgence of Taliban in Afghanistan, the nuclear flashpoint between the US and North Korea, and China's growing presence in the Indo-Pacific [18] In 2022, several Punjab Congress leaders, including former Chief Minister Captain Amarinder Singh and former Punjab party chief Sunil Jakhar left the Indian National Congress and joined the BJP, and subsequently Jaiveer Shergill also resigned from the Congress party in August 2022 alleging sycophancy in the party.