[1][8][9] Prior to the company's founding, Humphrey worked on the idea in his spare time, outsourcing the product's development and financing it with a AU$10,000 credit card debt.

[1][10][11] In November 2017, Dovetail was awarded the AU$25,000 minimum viable product grant from the New South Wales Department of Industry Jobs for NSW program.

[13] In February 2020, Dovetail announced a AU$4 million seed fundraising round led by Blackbird Ventures, with participation from Felicis Ventures and Culture Amp's CEO and co-founder Didier Elzinga to accelerate revenue growth.

[15] In 2023, Dovetail's headquarters moved to a new office spanning 4,300 square metres over four levels located on Sydney's historic Oxford Street.

[16][17] In January 2024, Ayers left the company after stepping down to an engineering role in the previous year.