Every aspiring CEO has heard of David Ogilvy’s famous admonition, usually paraphrased as “Hire people smarter than yourself” or words to that effect.  In my case, following that good advice has not been hard.  Applying that criterion has meant that I’ve had an enormous pool of qualified candidates to choose from.  As I’ve progressed in my career, however, I’ve come to believe in the importance of another, less discussed principle as the company grows:  Hire people who are different from you, and who will have the courage to challenge you when it matters.

Time to step up:  Hiring the VP of Sales

For the technology founder-led companies we love to back at Andreessen Horowitz, recognizing the need to “hire different” is particularly important when the company is transitioning from initial product development mode into sales mode.  If you’re an a16z founder, you’re very likely an engineer or computer scientist.  Virtually all of your early hires will have been engineers or developers.  While you’ve hopefully hired people who are smarter than you, they may not be that different from you.  Now you’ve got a product, it’s time to hire a VP of Sales.  Prepare to hire different—very different!

A typical sales culture is different from a typical engineering culture in almost every aspect—from personality types to values to dress code to working hours.   Introducing sales DNA is highly likely to clash with your engineering culture.  That prospect will feel quite uncomfortable, but is absolutely critical if you’re serious about building a real company.

While on an intellectual level you may recognize the need to hire an executive who’s different, it can be really hard to act on it in practice.  Most of us are naturally more comfortable with people who are like us.  If as a first-time tech founder CEO you feel entirely comfortable with that VP of Sales candidate, she’s probably not the right one.  The right candidate will feel risky to you from the cultural fit point of view.  So, you’ll want to know what the team thinks.  However, the interview feedback from the team is likely to make you even more uncomfortable.  Here are some real examples of technical team feedback from interviews of highly qualified sales candidates:

I’m worried that he’s rough around the edges and would clash with our people.”

“His tone was very A-type salesman.”

I fear for the culture if she were to come aboard.

He had very limited understanding of our product.

“I don’t think he has much idea of what we do and how we do it.”

“I think he could generate massive revenue, but he’d destroy the culture by building a Salesforce-type sales organization.”

So, hiring the right sales leader will involve not just overruling your own emotions, but rejecting the strongly held opinions of several members of your team.  Remember you’re not recruiting her for her knowledge of the company, but for her knowledge of the outside world.  As my partner Ben puts it: “Generally, you want product leaders with superior internal knowledge (knowledge of the code base, knowledge of the culture, knowledge of the people).  With sales people, it’s the opposite—they need to have external knowledge (knowledge of customers, purchasing processes, customer org structures, customer cultures, . . .)”.

Two-way street

While you and the team are trying to evaluate this unfamiliar animal and assess whether you can handle it in your habitat, don’t forget she’s evaluating you too.  Just as you’re asking yourselves things like, “Will this person destroy our culture?”, she’s asking herself, “Are these guys serious about building a business, and will I get the support I need to build a winning sales organization?  Will this CEO have my back with the company and the board?”  She won’t need everyone’s buy-in day one—a good VP of sales will earn that over time—but she will need full and sustained support from you and the board to put in place the processes, people and sales culture that can transform a great product organization into a great business.   This is your time to lead.  The way you handle the recruiting process will speak volumes about whether you’re the leader she wants to bet her career on.

Hiring different at Opsware

At Loudcloud/Opsware, we went though three VPs of sales in the first four years of the company.  Each one of them was well liked and an excellent fit with the culture, but not one of them was able to consistently hit our quarterly sales targets.  By 2003, looking for our fourth sales leader in as many years, we met a guy named Mark Cranney[1].  He seemed very well qualified, and he gave us several pages of references to call if we wanted proof.  However, virtually everyone who interviewed him had similar feedback:  “He might be a great sales guy, but there’s no way he’d fit here.  Way too risky.”

Ben Horowitz and I called every one of his references.  They confirmed that Mark was an exceptional sales leader who had consistently achieved great results.  But could we take the risk of introducing such a culturally different executive into Opsware’s strong culture?  Only Ben and I seemed to think so.  We hired him.

Hiring Mark, and the many sales professionals he added to our ranks, was indeed a shock to the system.  It created significant tension in the company at times, as sales culture met engineering culture.  It was a tension that we badly needed—a healthy tension between the demanding outside world of customer needs and competitive pressures and our sheltered inside world of PRDs and predictable development schedules.  Mark was unreasonable—he told it like it was, not how we wanted it to be.  It stretched every part of the company, from engineering to marketing to legal to finance.  Gradually, we became a more customer-driven organization and we started making our numbers.  Over time, cultural discomfort shifted to mutual respect and even to affection.  In the years that followed, we won hundreds of the world’s most demanding enterprise IT accounts, met their needs with market-leading products, outpaced a brutally tough competitor, and grew bookings and revenues at a rapid pace.  For Opsware, hiring different was the key to unlocking the company’s true potential.

The courage to challenge

Strong leaders don’t just hire people who are smarter than them, or different from them.  They also look for people who have the courage to challenge them, and they create a culture that encourages people to do so.  Ironically, being surrounded by lots of smart people makes it harder to speak up, particularly for more junior team members.  “If all of these smart people think X makes sense, who am I to challenge them?”  The more senior you are, the less likely you are to be challenged, and the more you will have to work to encourage it.  “She’s the CEO—she must know what she’s doing.  I’m not going to question it.”  I don’t know about you, but if I were the emperor, I’d want someone to tell me before I walked down the street naked.  Like the emperor, you won’t hear diverse opinions if you don’t actively solicit them—and resist the temptation to slaughter them with your ferocious intellect the minute they’re expressed!

At Andreessen Horowitz, we’re fortunate to have a lot of very smart people, more senior and more junior, around the table when we talk about companies we’ve just met.  It takes real courage to speak up when everyone else seems to love (or hate) some opportunity we’ve just seen, but we particularly want to hear that different view.  We work hard to encourage people to speak up.  The best investments are often controversial, and vigorous debate leads to better investment decisions.

The same applies to business decisions.  As CEO, it’s your job to make the call.  Having people around the table with the background and the courage to be controversial makes it more likely you’ll make the right one.  As your company grows, recognize that you’ll need to hire different, and strive to build a culture that encourages and rewards constructive challenge and diversity of opinion.

[1] Mark now runs the Market Development function for Andreessen Horowitz, connecting the firm and our portfolio companies with the world’s top corporations.