| $15M2024-06-05 | Sixfold Ai | Charles Birnbaum, Jeremy Levine |
| $31M2024-01-31 | Incognia | Charles Birnbaum, Sameer Dholakia |
| $32M2023-10-11 |  Upvest | Charles Birnbaum, Alex Ferrara, Jan Miczaika, Patrick Norris, Tim Rehder |
| $17M2023-10-11 |  Carefull | Bessemer Venture Partners, Charles Birnbaum |
| $31M2023-09-27 |  Farther | Lightspeed, Charles Birnbaum |
| $7M2023-05-24 | Sixfold Ai | Charles Birnbaum, Jeremy Levine |
| $9M2022-12-14 |  Nilus | Bessemer Venture Partners, Charles Birnbaum, Adam R. Fisher |
| $52M2022-09-01 |  Alloy | Felicis, Charles Birnbaum, Victoria Treyger |
| $11M2022-07-12 | Oper | Charles Birnbaum |
| $42M2022-06-16 | Upvest | Bessemer Venture Partners, Earlybird Venture Capital, Notion Capital, Partech, Speedinvest, Charles Birnbaum, Alex Ferrara, Patrick Norris |
| $180M2022-06-02 |  Guild | Charles Birnbaum, Byron Deeter, Kenneth Chenault |
| $15M2022-05-01 | Farther | Khosla Ventures, MassMutual, Cota Capital, Alphabet Inc., XYZ Venture Capital, Moneta Ventures, Charles Birnbaum |
| $17M2022-04-21 |  Basis Theory | Charles Birnbaum |
| $50M2021-12-15 |  Papaya | Sequoia, F-Prime Capital, Acrew Capital, 01A, Mucker Capital, Fika Ventures, Charles Birnbaum |
| $18M2021-12-14 | Staircase | Charles Birnbaum |
| $18M2021-12-14 | WEBBOXES | Charles Birnbaum |
| $100M2021-09-30 | Alloy | Charles Birnbaum, Victoria Treyger |
| $60M2021-09-29 | Betterment | Charles Birnbaum, Rob Stavis |
| $60M2021-07-28 |  Lithic | Nexus Venture Partners, Charles Birnbaum, Talia Goldberg, Mark Goldberg |
| $6M2021-07-21 | Onaroll | Charles Birnbaum |
| $60M2021-06-02 | Spruce Holdings | Charles Birnbaum, Rob Stavis |
| $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 |
| $43M2021-05-20 | Lithic | Charles Birnbaum, Talia Goldberg, Mark Goldberg |
| $220M2021-05-06 |  Shift Technology | General Catalyst, Advent International, Accel, Bessemer Venture Partners, Iris Capital, Charles Birnbaum |
| $3M2021-02-17 | Carefull | Bessemer Venture Partners, Charles Birnbaum, Rob Bernshteyn |
| $55M2021-02-03 |  Brightwheel | Charles Birnbaum, Vic Singh, Tim Young, Hadley Harris, Nihal Mehta |
| $—2020-12-14 | Brightwheel | Charles Birnbaum |
| $18M2020-10-28 | Fabric Technologies | Charles Birnbaum, Rob Stavis |
| $40M2020-09-16 | Alloy | ENIAC Ventures, Felicis, Primary Venture Partners, Charles Birnbaum, Vic Singh, Tim Young, Victoria Treyger, Brad Svrluga, Hadley Harris, Nihal Mehta |
| $29M2020-05-21 | Spruce Holdings | Charles Birnbaum, Rob Stavis |
| $160M2019-11-13 | Guild | Charles Birnbaum, Byron Deeter, Kenneth Chenault |
| $12M2019-09-17 | Alloy | Brad Svrluga, Charles Birnbaum, Hadley Harris, Nihal Mehta, Vic Singh, Tim Young |
| $60M2019-03-04 | Shift Technology | Charles Birnbaum |
| $21M2018-11-07 | Zopa | Charles Birnbaum, Rob Stavis, Jeppe Zink |
| $21M2018-10-02 | Brightwheel | Charles Birnbaum, Hadley Harris, Nihal Mehta, Vic Singh, Tim Young |
| $60M2018-09-18 | Bread Financial | Charles Birnbaum, Rob Stavis |
| $40M2018-07-25 | Guild | Felicis, Bessemer Venture Partners, Charles Birnbaum, Byron Deeter |
| $16M2018-07-19 | Spruce Holdings | Charles Birnbaum, Rob Stavis |
| $10M2018-06-19 | Fabric Technologies | Charles Birnbaum, Rob Stavis |
| $21M2017-09-06 | Guild | Byron Deeter, Charles Birnbaum |
| $130M2017-08-02 | Bread Financial | Charles Birnbaum, Rob Stavis, Adam Rothenberg, David Tisch |
| $70M2017-07-21 | Betterment | Charles Birnbaum, Rob Stavis |
| $5M2017-05-25 | Spruce Holdings | Charles Birnbaum, Rob Stavis |
| $3M2017-03-21 | Fabric Technologies | Louis Beryl, Charles Birnbaum, Rob Stavis, Adam Rothenberg, David Tisch |
| $25M2016-11-14 | Quantopian | Alex Rampell, Charles Birnbaum, Rob Stavis |
| $10M2016-09-19 | OMsignal | Charles Birnbaum, Rob Stavis |
| $1M2016-08-30 | Spruce Holdings | Charles Birnbaum, Rob Stavis |
| $—2016-05-27 | Fabric Technologies | Charles Birnbaum, Rob Stavis |
| $100M2016-03-29 | Betterment | Charles Birnbaum, Rob Stavis |
| $110M2015-12-11 | Zopa | Charles Birnbaum, Rob Stavis, Trevor Oelschig |
| $14M2015-11-10 | Bread Financial | Charles Birnbaum, Rob Stavis, Adam Rothenberg, David Tisch |
| $4M2015-09-03 | OMsignal | Charles Birnbaum, Rob Stavis |
| $33M2015-07-21 | BrightBytes | Charles Birnbaum, Rob Stavis |
| $60M2015-02-17 | Betterment | Rob Stavis, Charles Birnbaum |
| $15M2014-10-16 | Quantopian | Rob Stavis, Charles Birnbaum |
| $10M2014-06-24 | OMsignal | Rob Stavis, Charles Birnbaum |
| $32M2014-04-15 | Betterment | Rob Stavis, Charles Birnbaum |
| $15M2014-03-12 | BrightBytes | Rob Stavis, Charles Birnbaum |
| $14M2014-01-14 | Main Street Hub | Charles Birnbaum |
| $38M2013-10-21 | United Capital | Rob Stavis, Charles Birnbaum |
| $5M2013-10-21 | 2U | Rob Stavis, Charles Birnbaum |
| $10M2012-10-03 | Betterment | Rob Stavis, Charles Birnbaum |
