The Day I Sat with Sales


When I started at Box, I joined a world of coding and hacking where we were solved hard problems and build cool products. Sales was a mysterious realm that answered calls, talked a lot and took pranking each other to a fine art. In some abstract sense I knew they were bringing in the money that paid my salary, but mostly I knew them as the outgoing group that occasionally over-promised to customers (at my expense).

That all changed one day shortly after I joined. I asked our new COO (an engineer turned entrepreneur) how to grow in my career. His advice boiled down to this: expand outside the engineering department. Go sit with sales.

So I did. There was no approval process, I simply grabbed my laptop and found a free desk upstairs in the noisy sales room at sat down. I was a nervous and it felt awkward. I got a couple odd stares.

And nothing happened, of course. The sales team was a bit surprised but generally appreciated that an engineer was interested in coming to see what happened on the sales floor. I’d like to think I’d do the same if the situation were reversed, but I worry that engineers are trained to be suspicious of the rest of the company.

I wish I could say that I had a profound revelation, but that would be too neat. Really, I just sat and worked and heard the team take calls, make jokes, and type notes into Salesforce. It was only later that I learned what I was seeing was indeed profound.

Death of a(n overly aggressive) salesman

The archetype of the salesman from the pathetic Willy Loman to Alec Baldwin's swaggering "Always Be Closing" in Glengarry Glen Ross is going extinct. That guy (and he was always a guy) relied on a combination of charm and pressure to sell. He found prospects to court and wine-and-dined them into buying what he was selling. This caricature doesn’t just come from Mamet and Miller. Matthew Dixon and Brent Adamson, authors of The Challenger Sale, found that 54% of top-performing salespeople were controversial, assertive “challengers,” while supportive, team-oriented customer advocate types (“relationship builders”) were just 4%.

What I was seeing at Box flipped this formula on its head. These were "inbound" sales reps, fielding calls from interested people who were already using the free version of the product. Their job was not to be liked, and it was definitely not to hard-sell the product to suckers. You can't sell cutting-edge enterprise software the way you sell vacation rentals. Most customers were intelligent but distrustful of the new cloud technology. Charm wasn't going to convince the head of IT to trust Box with sensitive documents.

What I was seeing at Box was the new breed of sales, which Dixon and Adamson branded the "challenger" salesperson. Their goal was to deeply understand the customer's business and to teach them how they could do better using Box. They were absolutely still selling Box, but they were only effective it actually solved their customers' problems.

As I continued to return to the sales floor and meet the sales people I discovered that they rarely fit into my stereotypes. They were smart and deeply thoughtful. They joined Box because they liked the challenge of figuring out how to sell a brand new product in a brand new market. I watched them strategize about pricing and realized that this was every bit as complex as a problem in code. I also learned that yes, salespeople also sometimes dislike talking to strangers. The difference is that they approach it professionally and overcome the fear of rejection -- not too different from the way engineers must learn to systematically test their code and debug errors.

I also saw the way the VP of sales rigorously tracked all of his team’s key metrics and quantitatively decided what was working and what was not, in a way most product organizations can only envy. Sales at a company like Box is not about having a few talented sales people, but about building a scalable machine that can train new hires quickly to become effective salespeople. Sales is a numbers game, so the point is track leads, opportunities and deals every single week.

How hanging out with sales reps made me a better engineer

My interaction with salespeople profoundly changed the way I approach product development.I saw things through their lens: we want to create value for customers and ask for a fair price. Many features are popular but will not translate into increased sales because they ultimately don't provide value. Think about the products you love and would gladly pay for again. Then think about the products that if they doubled in price you would complain bitterly, but still pay for. That's what it means to create real value for your customers -- not just nice design or heavily requested features.

It would be overly simplistic to say that a salesperson’s mindset is equivalent to an engineer’s. Sales tends to be more competitive, and attract high-risk, high-reward types; on the other hand, lone wolf engineers often struggle, and given the potential downside of mistakes, we’re much more cautious about taking on risk. We write code and direct the product, and they spend their days listening to, advocating for and giving guidance to their prospects.

But great sales reps and great engineers have the same basic desire: to help solve other people’s problems. That’s why DataFox’s sales team is integral to our product: they’re a direct line to what our customers (including themselves) want and need. We as engineers get a front-row seat to the hardest part of sales: delivering the right message to prospects. And we’re committed to using data science to making that easier. It’s amazing what grew out of just a few days sitting with the Box sales team five years ago - and I highly recommend every engineer give it a shot.