How To Build The Future

Conrad recalls fixing computers as a student, working on Harvard’s newspaper, and leaving a slow-moving biotech career to start a company. His first startup, later renamed SigFig, spent years pivoting from a wiki for stock research and faced rejection from 70 investors. He advises founders to focus on making the business stronger instead of chasing investor trends.

Conrad started Zenefits to bring HR, benefits, and insurance administration into one system. YC pushed the team to launch early, and he says the urgency helped them get ahead of a competitor. He describes product-market fit as a strong pull from customers, contrasting Zenefits’ rapid response with years of failed ideas at SigFig.

After leaving Zenefits, Conrad believed employee data could support software well beyond HR. He and co-founder Pano spent about two years building Rippling with a mostly engineering team, aiming to avoid the manual operations that had burdened Zenefits. Conrad argues that connected applications can solve broader business problems and support shared investment in capabilities like analytics, permissions, and workflows.

Conrad expects AI to help larger companies operate with the agility of smaller ones by making more organizational information available to managers. He gives an example of performance management that reviews work products such as code changes, sales calls, and support tickets to surface employees who may need help. He also sees AI enabling software tailored more closely to specific companies and industries.

Conrad supports founders investigating problems directly when they persist through layers of management, such as by reviewing support tickets or listening to sales calls. He cautions that this approach is for important broken areas, not a substitute for strong executives or a way to intervene everywhere. He says Rippling still has a long way to go in proving its approach to business software.