When Zenefits banned vacations for employees, COO David Sacks went to the Caribbean

In the spring of 2015, Zenefits' then-CEO Parker Conrad promised that the two-year-old company would hit $100 million in revenue by the end of the year.

Based on such promises, Zenefits had raised $596 million in venture money and was valued at $4.5 billion.

It hired over 1,000 employees in 2015, roughly tripling its size. And with that breakneck pace of growth, the right hand stopped knowing what the left was doing.

Soon, multiple states were investigating the company for allegedly selling insurance without proper licenses and Zenefits wasn't on target to hit its sales goal, sources told Business Insider.

Zenefits told employees that they could not take vacations. It needed all hands on deck for the busiest quarter of the year.

But its COO at the time, David Sacks, ignored the vacation ban and left for the Caribbean, anyway, Bloomberg's Claire Suddath and Eric Newcomer report.

By February, 2016, Conrad suddenly resigned and Sacks, who had been COO since December, 2014, took over as CEO.

Where is David Sacks?

This idea that Sacks was often MIA echos what multiple former employees have told Business Insider. One employee told us Sacks had earned a reputation as constantly being on vacation, saying that Sacks and his wife, "all they did was vacation. I never once saw David Sacks, not once."

This person tells a story of how at the all-hands meeting, led by Conrad, "Someone would always inquire what's David Sacks working on. Parker's answer was always that he was working on 'customer acquisition costs and insuring they were not too high.' It was considered a company-wide joke. No one ever saw David Sacks. What's he working on, Parker. Where is he?"

Another former employee, who worked in the benefits department that was ultimately reporting to Sacks told us, "Parker was CEO. I didn't even know who David was."

Zenefits spokesperson Jessica Hoffman denies that Sacks was ever MIA. "This is incorrect. David attended almost every (if not all) All Hands meetings and was in the audience like everyone else. Parker preferred to be the only person presenting."

PTSD from working at Zenefits

Several former employees talk about their experience at Zenefits under Conrad as if it was traumatic.

As the new CEO, Sacks is now trying to change the company culture and its reputation. He banned alcohol at the office. He instituted a new company motto to "Operate With Integrity" and he told Bloomberg:

"The company culture of pressuring and bullying employees to cut corners and do the wrong thing is over.

Software? Or Insurance

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