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Delete Your History: Does Too Much Career Experience Turn Off Silicon Valley?

Even though I see myself as young and innovative, many tech companies wouldn't leap to that conclusion.

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Landing a job on the West Coast demands new head shots, and not just if you’re an actor.

I discovered this as I was looking for a way to turn my decades of experience in corporate communications into a job with a vibrant technology startup.

Friends told me that I had to change my image. My profile picture on LinkedIn and Twitter made me look too old, too heavy and too suit-and-tie for the Silicon Valley crowd.

So there I stood one day, getting a new photo taken in a T-shirt and sweater, as the photographer looked down on me from above — the perfect angle, he insisted, to minimize the size of my chin. When I unveiled the new photo to a friend who was familiar with my plans, he said, “Great, Steve. Now you only look 52, but that’s still 25 years too old.”

The idea that only the young are valued in Silicon Valley is now entrenched in common lore. Mike Judge uses his new HBO sitcom, “Silicon Valley,” to lampoon the tech world’s navel-gazing and self-aggrandizement. Noam Scheiber’s New Republic piece scored the Valley for its frattier qualities and ageism.

I knew the reality that someone my age would confront, but I also thought my combination of business experience and cultural connectedness could be valuable to the right company. Coaching young people as they proceed through their careers is a passion. I currently advise three professional cyclists on managing their public image. And at one company, I drew on my Nashville roots to identify a country-music group on the rise, incorporated them into our ad campaign, and helped propel them to the top of the charts.

But even though I see myself as young and innovative, many tech companies wouldn’t leap to that conclusion about me. To have any hope of appealing to them, I’d have to approach things differently than I would if I were pitching another big East Coast firm. So I did.

When I went out to Colorado to advise a friend’s sports-related startup, I forced myself to get a pedicure before heading to the office in flip-flops, shorts and a T-shirt — the de rigueur outfit for Boulder.

And when I prepared to meet with tech execs in Silicon Valley, I bypassed all the upscale New York clothing stores and went online to buy some tight, straight-leg pants that slimmed the sides and lifted the rear. I wouldn’t go full-hoodie, but I pretended I had never even heard of ties. I hid the BlackBerry, jettisoned everything but my iPad, and put on my sunglasses.

Not all my preparation was superficial. To get some perspective on where to focus my energies, I sought advice about the types of companies I should target. A friend who works in San Francisco educated me about the way the Valley works.

He categorized companies as either first-, second-, third- or fourth-generation. First-generation companies are startups, many of which don’t make it. They look for people who fit the vibe of a 24/7 culture in which everyone is passionate about getting an idea off the ground.

Second-generation companies often get through an initial public offering and then confront the challenge of trying to stabilize.

Third-generation companies are stable, with proven market appeal, often in a niche area.

Fourth-generation companies are long-standing, the type of company where I’ve spent most of my career — and therefore not the type of company that would offer new challenges.

My friend and I agreed that the best spot for me would be a second-generation company that could use an experienced hand to help make the transition to third-generation.

I met with a variety of people associated with well-known tech companies that still have a bit of proving to do. And while I made some solid connections with good people, I also ran up against several realities that anyone of similar age and experience is bound to encounter.

One is that what seems like success by most standards can be viewed with skepticism in Silicon Valley. For instance, I’ve served in a presidential administration and led corporate communications for The Wall Street Journal and a financial firm in the Fortune 100. For up-and-coming West Coast tech firms, the length of my resume — regardless of what was on it — led them to conclude, erroneously, that I’m not a disruptor.

Many in Silicon Valley also don’t view my current work as a plus. “So you’re on vacation?” one executive asked after I told him that I’m consulting.

A friend out West later said that I should have just explained that I was compensated well enough in my last job that I could be choosy about where to work next. Another adviser said I should let people know that I have money to invest in whatever company hires me — a whole new level of pay-for-play.

Throughout my search, I also discovered that despite my efforts to be available wherever and whenever someone wanted to speak, the people I interacted with often went out of their way to make it clear that I wasn’t a priority. My favorite experience was being told bluntly by a board member of a popular tech company, “I have 45 seconds left. Do you have anything else you have to say?”

Part of this need to impress seems to come from a desire to show that Silicon Valley doesn’t do things the way they’re done elsewhere, especially in such tired towns as New York and Washington, D.C. But while everyone in the Valley thinks they’re doing things differently and touts their creativity, they generally say the same thing, in the same tone.

This can lead to an almost cult-like insistence that whatever’s being done in the Valley is by definition the right thing to do. In an extreme case of shooting the messenger, one board member called me a liar when I suggested that the CEO of his firm said something in a public interview that might cause him some grief beyond the San Francisco Bay Area.

So is there any way for later-career executives to break through cultural differences and high-tech hubris and land a job in Silicon Valley? Based on my experience, they should consider a few things.

First, don’t pretend that you’re 40 (or 20) if you’re actually older. Think about the four generations of companies and figure out the one that would truly be the best fit for you. It’s probably not the first generation, no matter how cool you think you are.

At more advanced stages, companies need the perspectives of seasoned executives. The “no experience necessary — or wanted” ethos ultimately bumps up against reality. That’s why tech founders tend to bring in an executive their parents’ age — either of their own volition or because of pressure from the board –– when they hit the market. And when companies need a more robust presence in Washington to deal with government and regulatory issues, they don’t hire lobbyists right out of college.

Some startups quickly recognize this need for “adult supervision.” The founders of Pure Fix Cycles, a media-savvy manufacturer of bicycles popular in urban areas, hired a business-development veteran early on. But many growing companies don’t hire the right people until after their vulnerabilities have been exposed — partly because there are few people in early-stage companies who have the experience to anticipate what lies ahead. Entrepreneurs who are passionate about their product may be blind to pitfalls that outsiders can see coming.

Second, make it clear to prospective employers that you’re ready to do the frontline work yourself. Having managed big teams, I faced several questions about whether I would be willing to work in a smaller, less-hierarchical organization. The assumption was that I had gotten accustomed to delegating and to managing, but had lost my ability to do grunt work. I haven’t, but it’s hard to convince others that you’re just as comfortable being in the trenches with a team of three as leading a team of 300.

Third, make clear that you don’t expect to earn the same compensation you had at your most recent job. Part of the Silicon Valley experience is accepting less guaranteed income in exchange for more long-term potential. Embrace the risk. If you want the same salary you previously made, then you probably shouldn’t venture into a new sector.

Fourth, think of your work in Silicon Valley as term-limited. That may help you to convince companies that you’re willing to work as hard as a 25 year old, but probably not for a decade.

Finally, appeal to the upstart mentality of the companies you’re trying to win over. Don’t try to overlay your experiences onto a company that’s confronting challenges it perceives as new. Comparing the experiences of a new company to those of an established firm will raise questions about whether you’re creative enough to find new solutions or you’ll simply rely on what worked for you in the past.

It remains to be seen whether I can convince an edgy, youth-obsessed company to take a chance on someone with age and experience who shares their passion. I haven’t given up on Silicon Valley. Working in a vibrant, innovative culture would be exciting. And I’ve wanted to live in California since I was 17, back when it was hard for 17-year-olds to get good jobs in California.

Young companies may think adding some gray hair to the office signals that they’re letting go of their startup credibility. But by tech-world standards, hiring a 61-year-old really would be disruptive.

Steve Goldstein is an adviser specializing in executive and crisis communications. He previously served as head of corporate communications for Dow Jones/The Wall Street Journal, chief communications officer for TIAA-CREF and as the presidential appointee in charge of public affairs at the U.S. Department of the Interior. Originally from Nashville, he now lives in New York. Reach him @isg2.

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