Parker Conrad

Parker Conrad
Parker Conrad
Born	Parker Rouse Conrad 1980
Birthplace	New York City, United States
Nationality	American
Occupation	Entrepreneur
Title	CEO of Rippling
Known for	Co-founder of SigFig, Zenefits, and Rippling
Education	Harvard University (BA)
Children	2

Parker Rouse Conrad (born 1980) is an American entrepreneur and technology executive who has co-founded three startup companies: SigFig, Zenefits, and Rippling. He is the founder and chief executive officer of Rippling, a cloud-based human resources and workforce management platform valued at $16.8 billion as of May 2025. Conrad's career has been marked by both dramatic success and public failure; he rose to prominence as the CEO of Zenefits, one of the fastest-growing startups in Silicon Valley history, only to resign amid a compliance scandal in 2016 that became a cautionary tale about the risks of unchecked growth in the technology industry. His subsequent founding of Rippling, which he launched in 2016, has been characterized as one of Silicon Valley's notable comeback stories, with the company raising over $1.8 billion in total funding and Conrad's personal fortune crossing $2 billion. Conrad has advocated for a "compound startup" approach to building companies, arguing against the conventional Silicon Valley wisdom that startups should maintain narrow product focus.

Early Life

Parker Rouse Conrad was born in 1980 in New York City. He grew up in New York and attended The Collegiate School, a private preparatory school in Manhattan.

Conrad demonstrated early academic aptitude, particularly in science. In 1998, while still a high school student, he was among three New Yorkers to make the top ten in a national science competition, gaining early public recognition for his intellectual abilities.

Education

After graduating from The Collegiate School, Conrad enrolled at Harvard University, where he completed his undergraduate studies. His time at Harvard coincided with a period during which several notable technology entrepreneurs were attending or had recently attended the university, including Mark Zuckerberg.

Career

SigFig

Conrad's first major entrepreneurial venture was SigFig, an online wealth management and financial technology company. He co-founded the company and served as its CEO. SigFig developed technology to track and analyze investment portfolios, offering automated investment advice to consumers. The company positioned itself in the growing "robo-advisor" space that emerged in the years following the 2008 financial crisis.

Zenefits

Founding and Growth

Conrad co-founded Zenefits and served as its CEO, building it into one of the fastest-growing startups in Silicon Valley. Zenefits offered a cloud-based software platform that provided human resources services to small and medium-sized businesses, including payroll, benefits administration, and compliance tools. The company's business model was distinctive: it offered its core HR software free of charge and generated revenue by acting as a health insurance broker, earning commissions on the policies it sold through the platform.

Under Conrad's leadership, Zenefits experienced extraordinary growth. By the end of 2014, the company had been identified as one of the year's most prominent startup successes, with Forbes reporting that Zenefits had beaten out companies such as Uber and Airbnb to become "2014's hottest startup." The company attracted significant venture capital investment, and Conrad was named to Fortune magazine's "40 Under 40" list.

However, the rapid growth also attracted scrutiny. As a health insurance broker, Zenefits was required to hold proper licenses in each state where it operated. Reports emerged that the company had been operating in certain states without the proper insurance brokerage licenses, raising questions about its compliance practices.

Compliance Scandal and Departure

In February 2016, the compliance problems at Zenefits escalated into a full-blown corporate crisis. Investigations revealed that the company had, under Conrad's leadership, allowed employees to sell insurance without proper state licenses, and that an internal software tool had been used to help employees cheat on online licensing courses required by California regulators. The New York Times characterized the scandal as highlighting "the perils of hypergrowth at start-ups," pointing to Zenefits as an example of a company that had prioritized rapid expansion over regulatory compliance and corporate governance.

Conrad resigned as CEO in February 2016, with the company's board installing David Sacks as his replacement. The fallout was severe for both the company and for Conrad personally. By mid-2016, Zenefits had lost over half of its peak valuation, which Fortune reported had dropped significantly from its previous highs.

The consequences extended to regulatory action. The U.S. Securities and Exchange Commission (SEC) subsequently pursued enforcement action against both Zenefits and Conrad personally. Conrad and the company agreed to pay a combined fine of nearly $1 million to settle the SEC charges.

Rippling

Founding

Following his departure from Zenefits, Conrad co-founded Rippling in 2016 alongside Prasanna Sankar. Based in San Francisco, Rippling was conceived as a unified workforce management platform that would enable businesses to manage employee data across HR, IT, and finance functions from a single system.

Conrad's return to building a company in the HR technology space — the same industry where his previous venture had failed amid scandal — drew significant attention. Forbes characterized his founding of Rippling as "the comeback of a fallen tech unicorn CEO," noting that Conrad was attempting to build a company that addressed many of the same business problems as Zenefits but with a fundamentally different business model and corporate approach.

Growth and Funding

Rippling grew rapidly, attracting substantial venture capital investment over successive funding rounds. In May 2022, the company was valued at over $11 billion following a new funding round, as reported by Reuters.

The company continued to expand its product offerings beyond core HR functions. In September 2022, Forbes reported on Rippling's entry into financial management tools, describing the company's ambition to become "the Salesforce of employee data" by building a comprehensive platform that unified employee information across multiple business functions. By October 2022, Rippling had entered the spend management space and was expanding into global payroll services, extending its platform to serve international workforces.

In March 2023, during the collapse of Silicon Valley Bank (SVB), Rippling navigated a crisis that directly threatened its operations. The company secured a $500 million term sheet in just 12 hours as SVB was collapsing, a deal that TechCrunch described as a notable example of crisis fundraising in the technology industry.

In May 2025, Rippling raised $450 million in new funding at a valuation of $16.8 billion, bringing its total funding to approximately $1.8 billion. Bloomberg News reported that the deal brought the value of Conrad's personal stake to over $2 billion.

Compound Startup Philosophy

Conrad has been an outspoken advocate for what he calls the "compound startup" approach to building technology companies. In contrast to the prevailing Silicon Valley orthodoxy that startups should focus narrowly on a single product or problem, Conrad has argued that building multiple interconnected products simultaneously can create compounding advantages. Speaking at the SaaStr conference in April 2025, Conrad made the case that "the 'focus above all' mentality is not just limiting — it might" be actively counterproductive for certain types of businesses.

This philosophy has directly shaped Rippling's product strategy, which has expanded from core HR and payroll into IT management, spend management, global payroll, and finance tools, all built on a unified employee data platform.

Legal Dispute with Deel

In 2025, Rippling became involved in a significant legal dispute with Deel, a competing HR software company. Rippling accused Deel of corporate espionage, allegations that Deel denied. The dispute escalated in April 2025 when Deel filed a countersuit against Rippling alleging defamation and libel. The legal battle between the two companies attracted significant media attention within the technology industry, with Forbes reporting on the rivalry in the context of both companies' fundraising activities.

Personal Life

Conrad married Alexandra MacRae. Their wedding was reported in The New York Times wedding announcements in June 2011. He has two children.

Conrad resides in the San Francisco Bay Area, where Rippling is headquartered.

Recognition

Conrad was named to Fortune magazine's "40 Under 40" list during his tenure at Zenefits, which recognized him as one of the most influential young business leaders in the United States.

His founding and growth of Rippling following the Zenefits scandal has been the subject of significant media coverage. Forbes profiled his return to entrepreneurship in 2020 under the headline "The Comeback of a Fallen Tech Unicorn CEO," examining how Conrad was attempting to rebuild his reputation and career in the same industry where he had experienced a public failure. The Information also profiled Conrad's journey in depth.

In June 2025, Rippling was included on CNBC's Disruptor 50 list, an annual ranking of private companies considered to be reshaping their respective industries.

As of November 2025, Conrad's entrepreneurial trajectory — from the rapid rise and fall at Zenefits to the building of Rippling into a company valued at over $16 billion — has been cited as an example of resilience and second-act success in Silicon Valley.

Conrad is listed on the Forbes billionaires tracker, with his wealth primarily derived from his ownership stake in Rippling.

Legacy

Conrad's career has become a case study in two distinct narratives within the technology industry. The Zenefits saga is frequently cited in discussions of startup culture, growth-at-all-costs strategies, and the importance of regulatory compliance. The New York Times used the Zenefits story as a cautionary example of how rapid scaling can lead companies to cut corners on legal and regulatory requirements, with consequences for both founders and the employees and customers who rely on their products.

Conversely, Conrad's subsequent founding of Rippling has contributed to a counter-narrative about second chances in Silicon Valley. Unlike many founders who experience public failures and exit the industry, Conrad returned to build a company in the same sector, applying lessons from his Zenefits experience. Forbes and other outlets have examined this trajectory, noting that Rippling's growth and valuation suggest that investors and customers were willing to look past the Zenefits episode and evaluate Conrad's subsequent work on its own merits.

Conrad's "compound startup" concept has also contributed to a broader industry debate about product strategy. His argument that building multiple integrated products can yield advantages over a single-product focus has influenced how some technology founders and investors think about product development and market expansion, though the approach remains a subject of debate within the startup community.