It has long been a maxim of the technology industry that companies have to choose between building a culture around either sales or engineering. For those of us focused on the enterprise, the question is even more poignant, yet far less practical. And while Ben Horowitz contends that sales isn’t dead, startups keep trying to kill the sales function.

I’m often asked where Box’s culture falls and how that allegiance dictates our product and go-to-market philosophies, with the implication that any attempt at a middle-ground approach would dilute both culture and execution.

Unsurprisingly, the Valley has a strong bias towards hacker-centric engineering cultures. After all, isn’t the reason we build technology companies in the first place to avoid the hassle of unnecessary human interaction and friction? The Web is the great intermediary, theoretically negating the need for phone calls, price quotes, resellers, and so on. Self-service is the way of the future, and for many of us, it already represents an important part of our present. Sales organizations, then, are a relic approach, running counter to the promise of the Web, where software can be streamed on-demand.

We even go so far as to assume sales forces exist to compensate for inferior technologies. I’ll admit that before we had a sales team at Box, I assumed that companies that required sales to win were making up for some kind of product deficit. Just look at Oracle, SAP, or IBM: They move slowly, rarely innovate, and don’t build technology that users love. And they have remarkably strong sales organizations. Coincidence?

But this is where Silicon Valley and the rest of the world diverge. While everyone supports reducing friction, customers want the power to define what friction means to them. On Zappos, I can purchase shoes instantly with zero human interaction, but I can also call them if I have questions. And in the world of enterprise technology, buyers often want to be navigated by a product expert and have a representative voice when it comes to problems or suggested enhancements.

Do startups really have to choose? Can all-night hackathons, customer calls at 9am ET (a time unknown to any engineer), and face-to-face meetings with buyers coexist within the same company? Is it possible to take the innovation-driven engineering mindset of the consumer Internet and merge it with the go-to-market might that led Oracle and Siebel to global dominance?

Clash of the Cultures

When we decided in 2007 that our future at Box was selling to enterprises, terror set in. I imagined our culture would change overnight, and we’d wake up to an army of guys named Chuck and Chester* rolling around in Porsches, rocking gold watches and toting briefcases with smaller briefcases inside them. What would these new colleagues do to our vision and product?

My assumptions were extreme, but the underlying fear was real. We’ve seen it happen many times before in sales-centric enterprise software organizations: End of quarter deals that need just “one extra feature” drive product roadmaps off course. Firefighting issues in a litany of customer environments takes precious engineering time off of critical innovation initiatives. Worse, updates are promised based on customer timelines, with little consideration for what the engineering team is capable of meeting.

Given the fast-paced, transaction driven nature of sales, these organization often have little incentive to see through the long-term ramifications of such approaches to product design and development. Product perfection and value in the horizon is effectively traded for near-term profit. And so the dismantling begins.

Yet engineering-centric cultures aren’t much better at serving customers fully than their sales-centric counterparts. Amnon Landan, the early CEO of Mercury Interactive once said, “R&D guys are the smartest group in any company…But their logic is often wrong for customers.”  To deliver the best possible value for customers, you instead need a mix of different personalities and perspectives. Some of our greatest innovations at Box emerge from engineering tinkering, yet many others come directly from our customers – often steps ahead of vendors in their needs and desires for technology.

The product metrics and KPIs that startups live and die by these days tell us a tremendous amount about what users do within the confines of our technology, but they dramatically understate or miss entirely the contexts in which customers use our technologies. What challenges do people run into after they use your tool? What are your product’s bleeding edge use cases, which customers have discovered but aren’t even on your radar yet? A strategic sales organization can become a competitive advantage, not a distraction.

Building a Customer Centered Culture

We decided that there had to be a better way to build a sales organization, by combining a customer-centric culture with a business model that was far more aligned with customer success, and using sales to shorten the feedback loop for customer insights.

We’re not alone in striving for that elusive harmony between sales and engineering.  Companies like Workday, GoodData, Yammer, Zendesk, and many others have created environments where engineers are immersed in, rather than shielded from, the business model and needs of customers. These are environments where sales people are thoughtful of the needs, challenges, and priorities of the engineering team. David Ulevitch describes the cultural balance at OpenDNS as “a business culture driven by engineers.”

And with this model, you can take advantage of recurrent touch-points with customers and prospects to discover their needs and your gaps. Instead of siloing sales and engineering, turn proximity into a competitive assault by dramatically shortening the distance from customer feedback to product execution. Our ongoing investments in security, mobility, and platform have all been driven by constant conversations with customers. Incumbents like Oracle or Microsoft, however, take years to absorb customer feedback from the field, resulting in products that are misaligned with customer needs or far behind the realities of modern business.

Of course, it’s easy to say all of this when you’re small and nimble, but the question will be how to scale this kind of atmosphere and culture, as a company grows and conflicting demands increase. Fortunately, the SaaS business model naturally keeps the sales organization in check. The elastic and disposable nature of “rented” cloud solutions precludes selling something that isn’t real or isn’t successful, and it also keeps engineering on the hook for shipping what the customer paid for. Perverse incentives cannot survive in this model, at not for very long. The only way to succeed as a vendor is to deliver customer success.

When it comes to culture, balance doesn’t mean compromise. Companies that can align both sales and engineering around customer needs will have better insight into the innovations that will keep them relevant and the motivation to build them.

*I mean no offense to anyone named Chuck or Chester.**

**Unless you carry a briefcase within your briefcase.