Jonathan Heiliger: From Yahoo’s ISP To Facebook’s Infrastructure To Being A North Bridge VC

If you’re familiar with Jonathan Heiliger’s work, it’s probably because you used Facebook sometime in the last five years. He was the person in charge of keeping the site online as it grew from 35 million to more than 800 million users. Or, maybe you’ve encountered his efforts over the past decade and half when you logged online — because he helped build some of the core technologies and businesses that ran sites like Yahoo, starting fresh out of high school in the 90s.

Next time you hear about him, it might also be because of the next hot company that blows up in Silicon Valley. But this time he’ll be one of its investors. He’s joining North Bridge Venture Partners today, a firm that has quietly distinguished itself by focusing on infrastructure and enterprise startups over the last two decades.

His focus will include the infrastructure plays that have taken him from ISPs to Walmart to Facebook. But it will also span into consumer and consumer-IT startups — areas he’s gotten more exposure to recently. And with his years of experience in Silicon Valley, expect the dealflow to be good.

Heiliger, now a young 35, got his start straight out of high school in the heady days of 1995, when the world awoke shocked by the growth of early web. As a senior staffer at telecom company MFS Communications, he developed early web infrastructure, and helped to buy formative ISP UUnet.

In a well-timed move, he co-founded an early web hosting company in 1996 called Internet Systems, Inc. It built a data center in Mountain View, and landed Yahoo as an early client (and office neighbor — “lots of crazy stories,” Heiliger coyly tells me), along with a breadth of other names, including Netscape and Playboy. Sequoia invested, and convinced the startup to merge with Globalcenter, a spin-out of Global Village that featured a strong sales team. The combined property was headed towards an initial public offering when telecom giant Frontier Communications grabbed it for nearly $200 million.

Then, Heiliger won a ping pong game.

That is, 100 year-old Frontier had been building its infrastructure on the older ATM/frame relay network. Heiliger led a push for an “all IP” network, relying on internet protocols to send packets. While the move would set Frontier up to enable the most services the most efficiently out of any telecom, the change would be millions of dollars more expensive, which made the old guard balk.

So Heiliger ended up in a best-of-five ping pong challenge with Frontier’s vice president of finance. Although the company was mostly won over already, the game was a symbolic deal in which Heiliger stood to get a sizable bonus. He won — both the game and the technology bet. Frontier would go on to have the fastest network in the U.S. at the time, and also set the stage for his next move.

Startups at the time saw Yahoo on board, and the list of other clients, and were inspired by the forward-thinking approach. They started signing up to Frontier in droves. This in turn inspired Heiliger to take his first shot at investing. In the wild late 90s, the firm set him and partner Paul Santinelli with a $100 million fund to invest in web companies. As 20-somethings with no experience, they ended up bringing in a 4x return even as the bubble popped.

Not everything worked. “We were the first to come up with application service providers — the platform as a service concept,” Heiliger relates. “We said ‘we’re gonna drop storage into data centers and share systems infrastructures.’ We were having these conversations with Sun and Oracle about selling slices of their products so smaller companies could get access to them. That turned out to be something they weren’t interested in doing.”

As Silicon Valley fell into recession, Heiliger went straight back into startups, working at some of the most cutting-edge companies of the day. He spent three years at Loudcloud, “automating the sins of the previous generation of datacenters and application companies” — the company, which became Opsware, eventually sold to Hewlett-Packard in 2007 for $1.6 billion. Then he spent nearly two years at Danger, leading service operations for the device developer (that eventually inspired Android).

The middle part of last decade was marked by a few senior jobs at various companies large and small — Betfair, Walmart, and BubbleMotion — as well as a side gig as a technology advisor to various investors include Sequoia, Index and Accel.

That last firm was, of course, the first VC in Facebook. Jeff Rothschild, an Accel affiliate who had recently moved into the portfolio company to expand its tech team, tapped Heiliger to come in and help the company scale.

And the rest is recent history. While maintaining roughly 99% uptime during some of the fastest growth of any web company, ever, and growing his team from 40 people to hundreds, he also pushed forward new initiatives that are still shaking the infrastructure industry. After publicly criticizing the stodgy ways of existing networking companies, he initiated the Open Compute project, which developed a set of open-source server and data center technologies that were 38% more efficient and 24% cheaper than rival products. This also led the creation of the Open Network Foundation to help promote software-defined networking for the changing landscape of data growth in enterprises and web companies

Today, he’s getting back together with his old friend Santinelli, an entrepreneur and former Red Hat executive who has been a partner at North Bridge since 2005. The focus will be like what you hear these days from other top VCs — getting deep into the operations of growing companies, and using the partners’ expertise to help with key things like scaling. But don’t look for the firm to be going after the latest fads.

As Heiliger and Santinelli explain in an interview, their criteria for investing is as follows. The company “must go after a big market that you can disrupt, like Linux went after Windows, which was a huge market at the time.” The team “has to be the best, everyone has to contribute code.” And they have to “truly be building something different, that’s defendable, that’s really thought through — something that a big company couldn’t just pour person-years into and get a result from in six months.”

“I’m about partnering with entrepreneurs to build a company,” Heiliger says, “investing is a way to add value but so is time.” So entrepreneurs, get your pitches ready if you’re this serious. Heiliger starts at North Bridge today.