Apr
03
2019
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Rippling raises $45M at $270M to be the biz app identity layer

Parker Conrad’s last startup, Zenefits, drowned in busy work. Now with Rippling, he wants to boil that ocean. Instead of trying to nail one thing then expand, “very counter to conventional wisdom, we took on something that’s a lot broader and more ambitious.” That meant spending two years with 40 engineers working in stealth to build integrations with nearly every popular business tool to combine HR, IT and single-sign on services. The result is that when you hire an employee, Rippling onboards them to all those services in a single click. Goodbye, busy work. Hello, gateway to the enterprise app ecosystem.

The past few years have seen a Cambrian explosion of startups building specialty software for office productivity and collaboration. But that’s left customers struggling to get their teams set up on all these fragmented tools. As such, Rippling had a very good first year on the market with rapidly growing revenue. So when Rippling went out to raise money, Conrad was signing term sheets in just over a week.

Forty-five million dollars. “I know that rounds are bigger these days, but still, for a Series A, that’s pretty substantial,” Conrad tells me with a wide grin over coffee at San Francisco’s Four Barrel. “We want to keep doubling down on the engineering, investing and putting more money into R&D, so we have real product advantages and technology advantages over other players in our space, even though a lot of them have been around a lot longer than we have.” The Information‘s Zoe Bernard had reported Rippling was raising at least $30 million.

Rippling’s round was led by Kleiner Perkins and its enterprise guru Mamoon Hamid. As Conrad tells me, “Many of the metrics you use to evaluate SaaS companies were invented by Mamoon. He really knows his stuff. He’s also just a really great person.” Kleiner was his dream partner for Rippling. “I remember when I was in high school, Kleiner Perkins was the only VC firm I’d ever heard of. When I was a little kid, I thought ‘Oh that’d be cool some day.’ ” The round was joined by Initialized Capital, Threshold Ventures (formerly DFJ) and Y Combinator.

A source confirms the round was a stunning $270 million valuation. Hamid was also skeptical about Rippling trying to integrate with everyone before launch. But, he says, “What was a concern a few years ago is now something we like about the company.” After getting pitched so many piecemeal enterprise solutions, it suddenly clicked for Hamid why customers would want “one stop for everything. You need an independent party to be that glue layer.” 

Typically, enterprise software is an unglued mess. Apps don’t talk to each other, so when you hire a new employee, you have to manually add them, their role, their team, their manager, their permissions and more to every single tool your team uses. There are HR systems that control payroll and benefits, IT systems that determine what equipment you’re issued, productivity and collaboration apps like Slack and Dropbox and department-specific tools like Salesforce or GitHub. Conrad believes manually updating these with each hire, fire or promotion is the source of almost all administrative work at a company.

The willingness to slog through office chores rather than strategically nullify them is why Zenefits grew so fast, then suddenly hit a wall. What can be begrudgingly brute-forced at 50 employees becomes impossible to manage at 500 employees. That’s why, he says, “We don’t want to have anything that’s not software end to end in the product.” If it requires a client to call Rippling’s operations team for help, it could be built better. That maniacal focus actually allowed Conrad to temporarily hold Rippling’s only role responding to user complaints, which he also credits with propelling rapid iteration. The CEO wants to remain in that mindset, so he still lists his job title on LinkedIn as “Customer Support.”

Conrad seems to have convinced investors that though he was pushed out of his $4.5 billion-valuation HR startup Zenefits, he was more responsible for its rise than its fall. Conrad had built a script that allowed Zenefits staffers to stay logged in to the study portion of their insurance exam. Conrad insists it played no part in helping them study for or pass the certification test. Still, regulators got involved, leading to his departure and a combined $1 million SEC fine for him and Zenefits. The desire to speed things up was another symptom of busy work draining the company’s time.

There were also culture issues, with Zenefits once having to tell employees not to have sex in the office stairwells. A more measured pace and a deeper commitment to diversity are a few other ways Rippling hopes to avoid the culture troubles of Conrad’s last venture.

Rippling only truly began hiring more than engineers when it came out of stealth a year ago. Now the startup has established two lucrative business models. First, it earns reseller fees from other enterprise tool makers when people buy them through the Rippling gateway. Any developer with a well-established brand becomes an integrated Rippling partner. It’s not going to try to out-build Zoom or Mailchimp. “As Rippling is successful, what I think it can do is bring a lot of customers to these other businesses. If you can bring down the marginal cost of adding an N+1 business system, there’s a lot less hesitation about adding products.” Customers want more utility, just without the headache.

Meanwhile, Rippling develops its own in-house versions of undifferentiated parts of the HR and IT stacks, like PTO management or commuter benefits. Customers aren’t loyal to a brand in these areas yet, so it’s easy for Rippling to swoop in. And it can charge a similar rate, but beat competitors on convenience because its homegrown systems integrate directly with Rippling’s source of truth on employee details. Upstarts in the single-sign on space like Okta and LastPass claim to be identity layers, but are really just password managers. And their early growth has spurred SaaS companies to build API endpoints on which Rippling’s version RPass can piggyback.

For a while I thought Slack would emerge as the enterprise identity provider because chat is such a ubiquitous need that it could be the start of a cross-app profile. But HR and IT are an even more foundational layer, and Slack doesn’t feel like a natural place to gather employee details like Rippling is. “For slack, communication and collaboration in general are a big enough opportunity to not let identity get in the way of the core business there,” says Hamid.

Now with Rippling’s business revving up and plenty of cash to fuel the engine, Conrad tells me his biggest concern is hiring the right people. “The really challenging thing in a company is when the headcount grows too quickly. I’m making sure we don’t do things like more than double headcount in a 12-month period,” he tells me. While Zenefits was a mad blitz for scale, Conrad has tried to bias Rippling toward action without being so impulsive that the company makes mistakes. “It’s never easy, but we’re not yet at the scale where things become really scary. We have a little bit more time to hit milestones. We’re growing at a healthy clip, but nothing that’s straining things in any way and we see that because we track our NPS very closely,” he says of trying to run a business at a more livable pace while being an active dad, too.

Luckily, Zenefits taught him how to avoid many of the pitfalls of entrepreneurship. Conrad concludes that he’s happy to have gone from “playing video games on impossible mode versus medium mode.”

Oct
10
2018
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Zenefits’ Parker Conrad returns with Rippling to kill HR & IT busywork

Parker Conrad likes to save time, even though it’s gotten him in trouble. The former CEO of Zenefits was pushed out of the $4.5 billion human resources startup because he built a hack that let him and employees get faster insurance certifications. But 2.5 years later, he’s back to take the busy work out of staff onboarding as well as clumsy IT services like single sign-on to enterprise apps. Today his startup Rippling launches its combined employee management system, which Conrad calls a much larger endeavor than the minimum viable product it announced while in Y Combinator’s accelerator 18 months ago.

“It’s not an HR system. It’s a level below that,” Conrad tells me. “It’s this unholy, crazy mashup of three different things.” First, it handles payroll, benefits, taxes and PTO across all 50 states. “Except Syria and North Korea, you can pay anyone in the world with Rippling,” Conrad claims. That makes it a competitor with Gusto… and Zenefits.

Second, it’s a replacement for Okta, Duo and other enterprise single-sign on security apps that authenticate staffers across partnered apps. Rippling bookmarklets make it easy to auth into over 250 workplace apps, like Gmail, Slack, Dropbox, Asana, Trello, AWS, Salesforce, GitHub and more. When an employee is hired or changes teams, a single modification to their role in Rippling automatically changes all the permissions of what they can access.

And third, it handles computer endpoint security like Jamf. When an employee is hired, Rippling can instantly ship them a computer with all the right software installed and the hard drive encrypted, or have staffers add the Rippling agent that enforces the company’s security standards. The system is designed so there’s no need for an expert IT department to manage it.

“Distributed, fragmented systems of record for employee data are secretly the cause of almost all the annoying administrative work of running a company,” Conrad explains. “If you could build this system that ties all of it together, you could eliminate all this crap work.” That’s Rippling. It’s opening up to all potential clients today, charging them a combined subscription or à la carte fees for any of the three wings of the product.

Conrad refused to say how much Rippling has raised total, citing the enhanced scrutiny Zenefits’ raises drew. But he says a Wall Street Journal report that Rippling had raised $7 million was inaccurate. “We haven’t raised any priced VC rounds. Just a bunch of seed money. We raised from Initialized Capital, almost all the early seed investors at Zenefits and a lot of individuals.” He cited Y Combinator, YC Growth Fund, YC’s founder Jessica Livingston and president Sam Altman, other YC partners, as well as DFJ and SV Angel.

“Because we were able to raise a bunch of money and court great engineers . . . we were able to spend a lot of time building this fundamental technology,” Conrad tells me. Rippling has about 50 team members now, with about 40 of them being engineers, highlighting just how thoroughly Conrad wants to eradicate manual work about work, starting with his own startup.

The CEO refused to discuss details of exactly what went down at Zenefits and whether he thought his ejection was fair. He was accused of allowing Zenefits’ insurance brokers to sell in states where they weren’t licensed, and giving some employees a macro that let them more quickly pass the online insurance certification exam. Conrad ended up paying about $534,000 in SEC fines. Zenefits laid off 430 employees, or 45 percent of its staff, and moved to selling software to small-to-medium sized businesses through a network of insurance brokers.

But when asked what he’d learned from Zenefits, Conrad looked past those troubles and instead recalled that “one of the mistakes that we made was that we did a lot stuff manually behind the scenes. When you scale up, there are these manual processes, and it’s really hard to come back later when it’s a big hard complicated thing and replace it with technology. You get upside down on margins. If you start at the beginning and never let the manual processes creep in . . . it sort of works.”

Perhaps it was trying to cut corners that got Conrad into the Zenefits mess, but now that same intention has inspired Rippling’s goal of eliminating HR and IT drudgery with an all-in-one tool.

“I think I’m someone who feels the pain of that kind of stuff particularly strongly. So that’s always been a real irritant to me, and I saw this problem. The conventional wisdom is ‘don’t build something like this, start with something much smaller,’ ” Conrad concludes. “But I knew if I didn’t do this, that no one else was gong to do it and I really wanted this system to exist. This is a company that’s all about annoying stuff and making that fucking annoying stuff go away.”

Mar
14
2017
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Zenefits founder Parker Conrad takes another crack at HR onboarding

 Parker Conrad’s last venture at Zenefits didn’t end so well with his departure as CEO and the company having to re-orient itself. But he’s once again starting a company that will figure out how to build an employee system of record and management, starting off with smoothing out the process of on-boarding employees and focusing on other major life events for those… Read More

Sep
13
2016
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CEO David Sacks on moving on from Zenefits’ troubled past

disrupt_sf16_david_sacks-3714 Zenefits at one point was one of the fastest growing software companies in the world, rocketing to a $4.5 billion valuation in 18 months. It was on track to generate tens of millions of dollars in annual recurring revenue. Then, everything went south; regulators started investigating the company, and its CEO Parker Conrad was fired from the company earlier this year. In short, it’s been… Read More

Jul
25
2016
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Zenefits gets a small fine in resolving regulatory concerns in Tennessee

Michael Arrington interviews Yammer's David Sacks Zenefits has been under fire for skirting regulation, resulting in the ouster of its previous CEO Parker Conrad and a heavy-duty overhaul underway of the company. The results of that effort are now seemingly starting to emerge, starting first with a resolution in Tennessee which will cost the company $62,500 and allow it to continue operating. The company continues to have conversations with… Read More

Jun
30
2016
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Zenefits halves its previous valuation to $2B to head off investor lawsuits

Fireside Chat With Yammer Founder and CEO, David Sacks Zenefits is executing a change in its current ownership structure that will increase the overall ownership of the company for late-stage investors; it’s a move that revalues the company’s Series C round at $2 billion and looks to placate investor concerns over the company’s regulatory investigations. As part of accepting the new ownership changes, the investors… Read More

Feb
11
2016
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Zenefits Under Investigation In California

zenefits 6 The hits just keep on coming at the embattled cloud human resources software provider Zenefits, as the California Department of Insurance has begun an investigation into its licensing practic Read More

Nov
16
2015
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Zenefits Launches Its Own Payroll Platform

zenefits 6 Zenefits CEO Parker Conrad danced around a question about building out payroll services at Disrupt SF 2015. “I can’t announce anything about new products specifically, but you know payroll’s a very important spoke,” Conrad said at the time. But the cloud-based HR unicorn has built a payroll product, launching out of beta today. Read More

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