If you’re an IT enterprise seller looking to take a bite out of Apple, have we got the Emissary for you. Robert Sharpe, former senior director of global data center services at Apple, is our latest Emissary of the Month. We sat down with him recently to discuss what makes top tech companies tick, and what he’s seen salespeople do both right and wrong throughout his long and successful career.

The Best IT Businesses Change While Staying the Same

Now we see where Robert gets all that wisdom

Robert moved to the United States from Scotland in 1998, and settled in the San Francisco Bay Area in 2000. After stints at HP and Oracle, he was hired as the director of global data center services at Apple, where he would remain for the rest of his career.

Apple, as we all know, is a tremendously successful, almost trillion-dollar company (depending on the month). But as much as they’ve grown, little
has changed, and that, according to Robert, is the backbone of any successful organization.

“At the heart of truly successful companies, there isn’t much change,” he said. “Of course there is some on a technical level, but it’s essential to have a view for the long-term. Successful companies have become more agile, and are able to pivot, pursue, and achieve constant, well-thought-out goals.”

Apple has expanded into a variety of different spheres over the past decade from phones to wearables to streaming music and now, even television. All that has changed, it’s true, but it’s been backed by a consistent mindset and commitment to excellence—a set of core values which have never wavered.

“What I saw a lot of at Apple was a lack of organizational arrogance—don’t assume you’re going to be great just because you are great. I was always amazed by the lack of complacency. You can never rest on your laurels. As soon as you stop striving to be greater, and to maintain greatness, you lose it,” he said.

How to Sell Into Apple (or Anyone, Really)

Despite their immense size, Robert encourages salespeople to approach companies like Apple as they would any other. Understand the product and know your customer—those were the two pillars that supported all successful deals from Robert’s time on the buyer’s side.

“Through those two pillars, you’re able to gain an effective intersection between the selling company and the buying company, and it’s that intersection that creates a successful sale,” he said. “That’s what Emissary is doing—providing salespeople with an avenue to gain that customer knowledge.”

Robert recommends salespeople spend a lot of time on this crucial pre-sales stage. When sellers neglect to do their homework, it becomes evident in their dealings.

“I would see salespeople come in with this belief that Apple’s got a lot of money so it won’t be cost-sensitive. That’s not necessarily true. Apple’s got a lot of money because it is cost-sensitive. It goes back to understanding your prospect’s business fundamentals. You’re not going to sell a product because it’s cool, you’re going to sell a product because it adds value.”

Once you’ve mastered the two pillars of product and customer knowledge, Robert says to follow the “Four Es and a T”:

  • Ease of doing business: Are you a vendor that understands the importance of creating a true partnership?
  • Ease of transaction: Can you help facilitate the approval process and legal review?
  • Ease of implementation: Have you shown the roadmap for how your product can be assimilated into your prospect’s workflow?
  • Ease of operation: Have you provided your prospect with enough instruction or materials to guide pain-free usage on a daily basis?
  • Time to value: How soon can your prospect expect to see ROI?

If you know the right people to talk to and how to talk to them, and follow these guidelines closely, the selling process will go a lot more smoothly. “Not bothering to create a thoughtful intersection with the person you’re speaking to is fraught with danger,” Robert said. “If you don’t bother to create that you’re gonna fail.”

Robert the Emissary

Robert retired from Apple in 2017, and formed a consultancy to assist clients looking for data center expertise. He fills the rest of his days by satisfying both his love of learning and giving back.

He enrolls in one college course a semester to take on a new subject, and he’s also been a member of his local search and rescue team, taught financial literacy to children, and volunteered at a refuge for rescued parrots. When he’s not at work, you’ll often find him outdoors, or building something for his wife (most recently, a home yoga studio).

He also, of course, is an Emissary, where he enjoys feeding off of the passion of the salespeople he works with. “I’ve consistently enjoyed working with the people at Emissary,” he said. “Without a doubt, the successful engagements are those where the salespeople bring passion. For them, I think it’s almost a no-lose scenario. I would say it’s a better investment than numerous business meals or sports tickets, because it brings real customer knowledge and customer insights.”

Aside from advising sellers on the “Four Es and a T”, and the importance of knowing both your customer and their product, Robert emphasizes authenticity at every step of the way. Integrity and authenticity were core values of Robert’s leadership style, so whenever he sensed a lack of it coming from a vendor it made forming partnerships difficult.

“Know your customer,” he said. “Show them that you understand their business and demonstrate what kind of value you can create. If you do that, you’ll be creating a scenario that makes them excited to talk to you again.”

Executive Insights

Robert Sharpe, former senior director of global data center services at Apple, knows a thing or two about what it takes to sell into the enterprise. Never be intimidated by the large stage, and keep it simple by focusing on your product and the customer to build authentic, mutually beneficial partnerships with your buyer.