| Howden Group Holdings | $5 | United Kingdom | London | | |
| Coalition | $5 | United States | San Francisco | Joshua Motta and John Hering | 2017 |
| wefox | $4.5 | Germany | Berlin | Julian Teicke, Dario Fazlic, Fabian Wesemann, Jonathan Seoane, and Teo Martino | 2015 |
| Next Insurance | $4 | United States | Palo Alto | Guy Goldstein, Alon Huri, and Nissim Tapiro | 2016 |
| Digit Insurance | $4 | India | Bengaluru | Kamesh Goyal | 2016 |
| BGL Group | $3 | United Kingdom | Peterborough | Douw Steyn | 1992 |
| Ethos | $2.7 | United States | San Francisco | Peter Colis and Lingke Wang | 2016 |
| PolicyBazaar | $2.4 | India | Gurgaon | Yashish Dahiya, Alok Bansal, and Avaneesh Nirjar | 2008 |
| Accelerant | $2.4 | United Kingdom | Colchester | Jeff Radke and Michael Jackowski | 2018 |
| ManyPets | $2.35 | United Kingdom | London | Steven Mendel and Guy Farley | 2012 |
| Newfront Insurance | $2.2 | United States | San Francisco | Spike Lipkin and Gordon Wintrob | 2017 |
| Unqork | $2 | United States | New York | Gary Hoberman | 2017 |
| Earnix | $2 | Israel | Giv'atayim | | 2001 |
| bolttech | $1.5 | Singapore | | Rob Schimek | 2020 |
| Cambridge Mobile Telematics | $1.5 | United States | Cambridge | Hari Balakrishnan, Sam Madden, and Bill Powers | 2010 |
| Extend | $1.36 | United States | San Francisco | Christian Owens and Harrison Rose | 2012 |
| Marshmallow | $1.25 | United Kingdom | London | Alexander and Oliver Kent-Braham | 2017 |
| AgentSync | $1.2 | United States | Denver | Niji Sabharwal and Jenn Knight | 2018 |
| At-Bay | $1.12 | United States | Mountain View | Rotem Iram and Roman Itskovich | 2016 |
| Zego | $1.1 | United Kingdom | London | Sten Saar and Harry Franks | 2016 |
| Caribou | $1.1 | United States | Denver | John Puckett | 1992 |
| Acko General Insurance | $1.1 | India | Bengaluru | Varun Dua | 2016 |
| Kin | $1 | United States | Chicago | Sean Harper and Lucas Ward | 2016 |
| The Zebra | $1 | United States | Austin | Adam Lyons | 2012 |
| Shift | $1 | France | Paris | George Arison and Minnie Ingersoll | 2013 |
| Tractable | $1 | United Kingdom | London | Alex Dalyac, Razvan Ranca, and Adrien Cohen | 2014 |