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“Serial CIO” Yousuf Khan Discusses Investment in Lightyear

Ginger Woolridge
Lightyear is excited to welcome Yousuf Khan of Ridge Ventures to our Board of Directors.

Yousuf is a serial CIO-turned-investor who spent over two decades in IT leadership roles until 2020, at which point he joined Ridge Ventures as a partner focused on B2B software.

Yousuf is no stranger to early stage companies, however. With a successful track record of advising early stage companies as well as cultivating a multi city CIO “group therapy” community, Yousuf brings a wealth of enterprise IT-oriented go-to-market and customer success experience to the Lightyear team.

The Journey From CIO to VC

If there was an Iron Chef competition for cooking up an enterprise software venture capitalist, Yousuf has the winning recipe.

As one of only a small number of CIOs to successfully pivot into VC, Yousuf’s experience leading initiatives in everything from network infrastructure to security, business applications, and customer success has awarded him a reputation as a top-tier IT operator that is also strategic cross-functionally in sales, marketing, and overall strategy.

His roster of previous employers spans various industries and includes several public / multibillion dollar enterprises such as Pure Storage, Automation Anywhere, Moveworks, and Qualys - and in many cases, he was the inaugural CIO hire. In 20+ years of working in IT, Yousuf gained unique (and painstaking) insight into the issues facing IT teams today.

As Yousuf sees it, no matter your industry, the IT hurdles you face are consistent:

“Every CIO and their IT teams are constantly strapped for budget, resources and time. I faced this issue on every IT team I’ve ever led. I hear about it from every CIO I connect with. The true job of the IT team is to build and deploy networks. However, anytime your company wants to set up a new office or data center your IT team is forced to play the procurement team, and they waste a lot of time in the process.”

But Yousuf isn’t one to sit back and accept the status quo. He got into advising early stage startups so he could help build the companies that were trying to solve the very issues he was facing at work. Yousuf takes pride in his advisorship selectivity; he has yet to work with a company where he wouldn’t actually use the product himself as a CIO. This strategy has certainly paid off as his early stage advisorships include successful startups such as Zoom, Pulse, Material Security, Oomnitza and Productiv.

Was his involvement key to these successes or was it simply coincidence? Ridge believes it to be the former, as they tapped Yousuf as an advisor three years prior to hiring him as a partner in 2020.

When he wasn’t advising early stage companies, Yousuf was hosting a monthly dinner series called “CIO Group Therapy” in the Bay Area. The event cultivated a strong community of CIOs where the tongue-in-cheek name resonated on another level.

When he isn’t educating the Ridge investment team with what they have dubbed “Khan-isms”, Yousuf enjoys croissants, playing cricket, and sipping on a cold Dr. Pepper. Oftentimes, you’ll catch Yousuf wearing one of his signature sweater vests when he’s out and about.

Lightyear Mission Hits Home

Lightyear’s Co-founder and CEO, Dennis Thankachan, was first introduced to Yousuf by a friend who thought he could be a valuable mentor and potential advisor to the Company. On their first video call, Dennis started off by sharing the high-level Lightyear value proposition. As Dennis was pulling up a shared screen to demo the platform, Yousuf described his ideal product interface for this type of software - and to both of their amusement, that’s exactly what Lightyear had already built.

“I was awestruck when I first saw the quote comparison interface. I thought to myself ‘I know hundreds of CIOs and IT Directors who would want to use this tool,’ that’s when I knew Lightyear was a company I wanted to be a part of.”

The conversation quickly turned into an investing endeavor for Ridge thereafter.

Lightyear's software platform allows businesses to buy and manage their network services online. In Yousuf’s opinion, Lightyear’s software provides a complete 180 from the way B2B telecom is procured and managed today.

“The B2B telecom ecosystem is so manual and archaic - this is a several decades old problem. It forces IT teams to spend a tremendous amount of time on their network just to make suboptimal decisions,” Yousuf added, “When I was at Pure Storage and Automation Anywhere, anytime we opened a new office my team spent way too much time researching providers and talking to ISPs. After a circuit was bought, we had minimal visibility into our network inventory because it was managed in an Excel spreadsheet. If we had Lightyear back then we could have done so much more.”

Change Making is a Challenge

If these issues are so painstaking, why have they stuck around for so long?

Yousuf believes that inefficiencies in the B2B telecom space have held strong primarily due to a sub-par status quo being accepted as reality. Many IT teams work with independent brokers or telecom agents who offer the value of a long term relationship, but are not vendor agnostic or data driven which often results in suboptimal decisions (whether IT teams realize it or not). Some IT teams might not be equipped with the knowledge (or, more likely, time) to understand that their telecom services are overpriced and network management processes are inefficient. Other IT teams might be curious about a better alternative, but are simply willing to accept that they don’t stand a chance to “optimize” given the state of the market.

The other primary reason that the sub-par status quo has persisted is simply that no one capable has come around to fix it - until now.

“Change management is hard in any industry, but especially in one where you have both customers and suppliers who are unaware, incapable, or unwilling to modernize the way they do business,” Yousuf noted, “Until recent years, the APIs, infrastructure, partnerships, and general understanding of telecom network pricing was not readily available.”

Stand-Out Remote Team “Meshes” Well Together

Product aside, Yousuf clicked with Dennis and the team right off the bat when discussions ensued in early 2020.

Yousuf noted that Lightyear has built a team of talented individuals who “mesh” extremely well together. He considered the team culture impressive for an early stage company, especially considering the Company was built on a fully remote basis.

And when it comes to partnership, Yousuf and Ridge’s compatibility with Lightyear made sense from the start. As Yousuf puts it, “How many VCs have you met who have actually been in a data center and set up circuits?” Lightyear adds, how many VCs have you met who could make the “meshed” network joke?!

Ridge Ventures is a great partner considering it’s experience with other successful early investments in Fastly, Discord, and Braze, to name a few. Lightyear is ecstatic to be joining Ridge’s roster of early stage investments.

The Real Job of IT Teams

As an ex-CIO himself, Yousuf is passionate that the real job of IT teams is to build and deploy networks, but sadly they are always tasked with much more.

When he saw how Lightyear’s platform could save time and energy on behalf of the IT teams he used to lead, joining the Lightyear team was a no-brainer.

“If I had Lightyear’s product 20 years ago I could have done a lot more in terms of saving time and making smarter telecom decisions - I would have been a better CIO for it. Lightyear is optimizing IT team productivity and enables them to be more impactful than ever before.”

Welcome to the team, Yousuf!

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