P arker Conrad is a controversial but resilient American technology entrepreneur who has founded two 'unicorn' startups in the human resources software sector. He grew up in New York and attended Harvard University, though he was known for his academic struggles, which he has spoken about publicly. His first major success was Zenefits, an all-in-one HR, payroll, and benefits platform that he co-founded in 2013. Zenefits offered its core software for free, making money from commissions on the health insurance plans it sold to its client companies. This disruptive model led to explosive growth, and the company quickly achieved a multi-billion dollar valuation.

However, Zenefits' rapid ascent was followed by a dramatic fall. The company faced major compliance issues, including allegations that it was using unlicensed brokers to sell insurance. The scandal led to regulatory investigations and forced Conrad to resign as CEO in 2016. Undeterred, Conrad made a remarkable comeback. Later that same year, he founded Rippling, another HR tech company. Rippling took a different approach, building a comprehensive platform to manage not just HR and payroll, but also IT services like app provisioning and device management. Rippling also grew rapidly and has achieved an even higher valuation than Zenefits did at its peak, marking one of the most significant second acts in recent Silicon Valley history.