NameWhat they do Employees ImpactedPercentRaised
DatarobotDatarobot provides a platform for automated machine learning and AI.1,10020018%$431M
Clover HealthClover is a health care insurer that focuses on  Medicare Advantage.56014025%$975M
MetromileMetromile offers pay as you drive insurance as well as a white label claims management system.30310033%$293M
Newfront Insurance They are a risk manager and broker that has rethought their business using technology and enhanced processes.2509036% 
DomoDomo provides a cloud-based BI and analytics system.9009010%$690M
OscarOscar is a digital-first health insurance company.1,400705%$1300M
Bold PenguinBold Penguin has created an online commercial insurance exchange for independent agents.1504026%$51M
NautoNauto is an AI-technology company that’s improving the safety of commercial fleets with an IoT device.1884021%$174M
Enigma TechnologiesEnigma provides alternative small business data.853440%$130M
JettyJetty sells rental insurance to tenants and acts as a guarantor on leases in exchange for 5 percent to 10 percent of the annual rent.753040%$40.5M
Slice LabsSlice provides a technology platform to deploy on-demand insurance products.  They also market their products.852833%$36M
TrovTrov provides the technology needed to launch on-demand insurance products.792633%$114M
Blink HealthBlink Health created an online way to get and manage prescriptions.2362511%$165M
Ladder LifeLadder has reinvented life insurance to offer instant, fully underwritten term policies online. 521325%$94M
Pillar TechnologiesAn IoT firm that makes sensors for construction projects allowing for real time risk management.16  $3M
Heap Heap offers a smarter way to build digital products.  Esurance is 1 client.186  $95M
RisksenseRisksense provides full spectrum cyber risk-based vulnerability management112  $24M
SnapsheetSnapsheet provides and end-to-end, cloud-native claims management platform that leverages technology to allow for remote capture of information.305  $66M
ADDING
EnsuremEnsurem sells Medicare supplement insurance by enhancing the sales process with technology. ~50 80 $14M
(Sourced from web searches and http://layoffs.fyi/tracker/)