Winning? The company is a giant mess, and the shit has not even hit the fan yet, this is just the start.
Parker didn't accomplish anything positive as CEO of Zenefits, ever. There's a ton of companies using Zenefits services who aren't happy. They haven't left because switching is a major pain in the ass. You think it's by accident that Parker chose to disrupt three of the industries with the highest customer retention rates. This board knows damn well that it's not because the (industry) solutions are awesome, it is because switching is painful and costly. Zenefits overall customer satisfaction sucks, as does feedback from employees and overall morale, check GlassDoor.
Parker found a way to piss off not just one highly regulated industry (health insurance) but three. He told a "journalist" from BI that the CEO of ADP "threatened him like Dirty Harry" in true SF/SV tabloid fashion. You think Warren Buffet ever did something like that?
From day one, on stage at TC Disrupt, he acted like a cocky spoiled brat, which is precisely what he is.
He managed to create enemies with many of the companies Zenefits originally did business with, and then relished in it when it made headlines, ala "project nutshot".
Zenefits is a company that is not only on track to lose hundreds of millions of its investors money, but it literally put its employees freedom at stake. People could be facing jail time because of how blatantly Zenefits ignored the law. More than 80% of sales in WA were by unlicensed reps. Tip of the iceberg.
Had Zenefits reached a $60M run rate without breaking the law, without requiring over $500M in VC, without requiring a near $100M burn rate, without Parker being abusive and unprofessional, well I'd have no choice but to congratulate Parker on his accomplishments.
All this guy did was burn through a ton of money, make a fool out of his investors and mismanage this company to the point where the massive fundraising at a $4.5B valuation, and all but inevitable write down, have sent every employees shares into a watery grave.
Learn from this. Don't try to romanticize the Zenefits story. If you look beyond the PR machine, you'll find a company that has done almost everything wrong under the helm of someone who was more interested in accomplishing something for himself, "proving people wrong", because of the self-described chip on his shoulder.
Just be glad you're not David Sacks, because unwinding this mess is going to be nearly impossible, and investors are going to be brutal. I wouldn't want to have to answer to Jordan Catalano.