| $200M2025-06-14 |  Ramp | Kenneth Chenault, Hemant Taneja, Alex Tran, Samir Kaul, Keith Rabois, Brandon Reeves |
| $200M2025-06 | Ramp | Samir Kaul, Napoleon Ta, Keith Rabois, Kenneth Chenault, Hemant Taneja, Alex Tran |
| $9M2024-10-29 |  Sapien | Niko Bonatsos, Kenneth Chenault, Max Rimpel |
| $150M2024-10-29 |  Melio | Adam R. Fisher, Kenneth Chenault |
| $150M2024-10 | Melio | Kenneth Chenault |
| $9M2024-10 | Sapien | Scott Belsky, Niko Bonatsos, Kenneth Chenault |
| $150M2024-04-17 | Ramp | Kenneth Chenault, Alex Tran, Keith Rabois |
| $150M2024-04 | Ramp | Keith Rabois, Kenneth Chenault, Alex Tran |
| $200M2024-01-24 |  Bilt | General Catalyst, Eldridge, Prosus Ventures, Left Lane Capital, GID, Camber Creek, Kenneth Chenault, Joel Cutler |
| $200M2024-01 | Bilt | Kenneth Chenault, Joel Cutler |
| $300M2023-08-21 | Ramp | Kenneth Chenault, Alex Tran, Keith Rabois |
| $300M2023-08 | Ramp | Keith Rabois, Kenneth Chenault, Alex Tran |
| $220M2022-06-08 |  Multiverse | General Catalyst, Lightspeed, D1 Capital Partners, GV, StepStone Group, Index Ventures, BOND, Audacious Ventures, Kenneth Chenault, Joel Cutler |
| $180M2022-06-02 |  Guild | Charles Birnbaum, Byron Deeter, Kenneth Chenault |
| $180M2022-06 | Guild | Kenneth Chenault |
| $220M2022-06 | Multiverse | Kenneth Chenault, Joel Cutler |
| $100M2022-03-31 |  Chief | General Catalyst, GGV Capital, eCAPITAL Entrepreneurial Partners AG, Inspired Capital, Primary Venture Partners, Flybridge Capital Partners, Kenneth Chenault |
| $30M2022-03-16 | Bambee | Kenneth Chenault |
| $30M2022-03 | Bambee | Kenneth Chenault |
| $100M2022-03 | Chief | Kenneth Chenault |
| $15M2022-02-17 | Relief | Kenneth Chenault |
| $28M2022-02-01 | withco | Kenneth Chenault, Keith Rabois |
| $15M2022-02 | Relief | Kenneth Chenault |
| $28M2022-02 | withco | Keith Rabois, Morgan Livermore, Kenneth Chenault |
| $130M2021-09-28 | Multiverse | General Catalyst, D1 Capital Partners, GV, Index Ventures, BOND, Lightspeed, Latitude, Audacious Ventures, Kenneth Chenault, Joel Cutler |
| $250M2021-09-14 | Melio | Adam R. Fisher, Kenneth Chenault |
| $250M2021-09 | Melio | Kenneth Chenault |
| $130M2021-09 | Multiverse | Kenneth Chenault, Joel Cutler |
| $150M2021-06-02 | Guild | General Catalyst, D1 Capital Partners, Redpoint Ventures, Salesforce Ventures, Cowboy Ventures, GSV Ventures, ICONIQ Capital, Charles Birnbaum, Byron Deeter, Kenneth Chenault |
| $150M2021-06 | Guild | Kenneth Chenault |
| $110M2021-01-25 | Melio | Adam R. Fisher, Kenneth Chenault |
| $110M2021-01 | Melio | Kenneth Chenault |
| $26M2020-12-14 | Well | Kenneth Chenault, Joel Cutler |
| $26M2020-12 | Well | Kenneth Chenault, Joel Cutler |
| $80M2020-09-08 | Melio | Adam R. Fisher, Kenneth Chenault |
| $80M2020-09 | Melio | Kenneth Chenault |
| $15M2020-05-21 | Chief | General Catalyst, GGV Capital, BoxGroup, Inspired Capital, Primary Venture Partners, Flybridge Capital Partners, Kenneth Chenault |
| $15M2020-05 | Chief | Kenneth Chenault |
| $160M2019-11-13 | Guild | Charles Birnbaum, Byron Deeter, Kenneth Chenault |
| $160M2019-11 | Guild | Kenneth Chenault |
| $22M2019-06-25 | Chief | Kenneth Chenault |
| $25M2019-06-01 | Well | Kenneth Chenault, Joel Cutler |
| $25M2019-06 | Well | Kenneth Chenault, Joel Cutler |
| $22M2019-06 | Chief | Kenneth Chenault |
| $140M2018-07-31 |  Gusto | General Catalyst, Kleiner Perkins, Emergence Capital, 137 Ventures, BDT & MSD Partners, T. Rowe Price, Ken Chenault Jr., Louis Beryl, Kenneth Chenault |
| $140M2018-07 | Gusto | Kenneth Chenault, Ken Chenault Jr., Hemant Taneja, Louis Beryl |
| $3M2017-10-12 | Beauty Bakerie Cosmetics Brand | Ken Chenault Jr., Kenneth Chenault |
| $3M2017-10 | Beauty Bakerie Cosmetics Brand | Kenneth Chenault, Ken Chenault Jr. |
| $50M2015-09-15 |  Compass | Founders Fund, American Express Ventures, Salesforce Ventures, Institutional Venture Partners, .406 Ventures, Thrive Capital, Kenneth Chenault |
| $50M2015-09 | Compass | Kenneth Chenault |
| $40M2014-07-21 | Compass | Kenneth Chenault |
| $40M2014-07 | Compass | Kenneth Chenault |
| $8M2012-12-17 | Compass | Ken Chenault Jr., Kenneth Chenault |
| $8M2012-12 | Compass | Kenneth Chenault, Ken Chenault Jr. |
