In Silicon Valley: A Time for Authenticity

A recent New York Times article suggested that boring is the new black for tech CEOs. The piece argued that confrontational, in-your-face CEOs like Uber founder Travis Kalanick are now more liability than asset. Instead, low-key, unassuming, middle-of-the-road CEOs like Dara Khosrowshahi, Kalanick’s replacement, are the best execs to lead companies in Silicon Valley.

While I would hesitate to call any CEO boring, I do believe there is a growing need for “authentic” leadership in technology. What do I mean by that? I mean CEOs who are open, transparent and honest, as opposed to those who are constantly in marketing mode, storming the battlements of the status quo with whatever weapons they decide are most effective.
But even more important, authentic leadership means CEOs who think and act like their core customers.

Let me take a step back here, because this is a critical point. Increasingly, I think it’s necessary for almost every emerging enterprise technology company to address a particular job title and to own that job title by delivering to it a very compelling solution. For example, Salesforce.com: it has grown to be one of the most successful software companies of all time by owning the VP of Sales job title.

Tech companies of the future will live or die based on how well they serve a particular job title, whether it’s VP of Engineering, VP of Field Operations, VP of Manufacturing, VP of Compliance—the list goes on. That’s why, in every meeting we take, we ask the entrepreneur: what job title are you building your business around?
Authentic leaders can answer right away, because they care first and foremost about the job title their business serves. They don’t just want their customers to be successful—they want them to be heroes within their organizations.

Take a CEO like Marc Benioff in the early days of Salesforce. When Benioff sat down in front of sales executives, he immediately connected with them, because he could speak their language. Basically, he was one of them. He worked in sales and marketing during his years at Oracle and, as CEO of Salesforce, he could talk eloquently and emotionally about the future of sales and his product vision. And sales execs loved him for it.

By way of contrast, let’s say a more practical CEO sits down with a VP of Sales. It’s unlikely that CEO will inspire the same level of trust and confidence as a Marc Benioff. In other words, that CEO would not feel as authentic.

Similarly, if you put a big personality in front of a VP of Supply Chain, you might get a negative response. Supply chain executives are all about specifics and they’re inherently skeptical. If you’re selling them a piece of software, they want to know how not only it will work for them today, but how it will help them two or three years from now. That requires a leader who is slightly more practical and slightly less salesy.

The message here is that when you’re building a company around a job title, it’s critical to ask what that title really needs from you as a leader. Authentic leadership is all about the ability to resonate with a particular customer persona.

Take, for instance, the job title VP of Field Service. These are executives who live to solve the hardest problems under the most pressure-packed circumstances. They and their teams prepare for that moment when it’s 100 degrees in the middle of August and the air conditioning goes down in a large apartment building. They understand that deploying the right field service technician with the right part at the right time can be matter of life and death.

That’s why the CEO of a company targeting the VP of Field Service needs to be someone with deep experience in the industry. They don’t have to be a flashy marketer and they don’t need to be someone who is overly promotional. They do need to be credible and trustworthy, which means they need to be someone who cares deeply about the role of field service techs and wants to make those people superstars within their organizations. They need to believe that field service workers are cool and that their business issues are incredibly interesting and mission critical. That’s how a CEO earns their trust and ultimately solves their problems.

By the same token, let’s say you’re a CEO who’s calling on the VP of Consumer Marketing at a big-brand company. You’d better look the part. You’d better look like you just walked out of some big advertising, PR or digital marketing firm. You’d better know that customer inside and out, what appeals to them, and how to speak their language when you sit down with them.

As a founder of a venture capital firm, I think a lot about the CEOs who lead our portfolio companies. In fact, in many ways this is the secret sauce of our business. Contrary to what the New York Times suggests, I don’t think Silicon Valley is now looking for boring leaders. What we are looking for is highly competent, authentic leaders who map perfectly to job titles they’re building their companies around. Because the more authentic the leader, the more successful they’ll be.


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