Kaljulaid began his political career in 2002 as a public relations advisor of Edgar Savisaar, the then Mayor of Tallinn and father of his partner at the time Maria.

[7] He left the position in 2004 and went on to create his own marketing and public relations company which became the main organiser of Centre party's bull sheet election campaigns for the next 15 years.

[9] He was suspected in abetting embezzlement in connection to the corruption probe into Center Party Chairman Edgar Savisaar, but the Prosecutor General dropped the charges due to lack of public interest in the proceedings with Kaljulaid agreeing to pay 1,000 euros into state budget and 800 euros to cover the cost of an expert opinion.

[15] In 2020 Kaljulaid was elected as the leader of the Social Democrats in the capital city of Estonia, Tallinn.

[16] In 2021 the Social Democrats picked Kaljulaid as their candidate for the Mayor of Tallinn in the 2021 municipal elections.