It’s the end of the month, and deals are being done against deadlines here at Salesforce. The energy is intense, as teams push to close those last few deals that will tip the scales in our favour. For those of us who’ve been in the game a while, this isn’t anything new—just another end-of-month crunch. But as I think back to how things used to be, I realise just how much the sales landscape has evolved.
I’ve been around long enough to remember when closing a deal was far from the streamlined process it is today. There was no DocuSign or instant communication—just a lot of waiting and a bit of praying. I can still recall the anxiety of waiting for orders to come through the post, and the occasional frantic drive to a customer’s office when the post didn’t arrive on time. And let’s not forget the occasional fib from a customer who claimed they had sent the order when they hadn’t.
Back then, salespeople had to get creative. If a fax machine was the only way to get a signature, you’d find yourself asking customers to knock on a neighbor’s door or head to the local post office or hotel lobby. It was all part of the job. We did what we had to do to get that order signed and delivered before the deadline.
But even those stories can’t compete with some of the more legendary tales in sales history. Take, for instance, the famous “Helicopter Deal.” This story, often associated with a sales exec from IBM in the 1990s, has become part of sales folklore. The story goes that the salesperson, facing a critical deadline and a non-functional fax machine at the client’s remote office, chartered a helicopter to personally pick up the signed contract. The salesperson then flew back just in time to meet the deadline, securing a multi-million dollar deal. Whether every detail is true or slightly embellished over the years, it captures the lengths salespeople have gone to when the pressure is on.
But the helicopter story is just one of many examples of salespeople going to extraordinary lengths to close a deal. In the early days of Salesforce, the hustle was no different. Marc Benioff, the co-founder of Salesforce, is known for his relentless drive and unconventional tactics to win customers. One such story that has been circulating for a while involves Benioff’s persistence in securing a deal with a major financial institution. After multiple attempts to get a meeting with the decision-maker, Benioff apparently finally managed to get the executive’s attention by showing up unannounced at the company’s headquarters with a cake in hand, decorated with the Salesforce logo. The bold move paid off, and the deal was eventually signed .
Another well-known example from the tech world is Oracle’s aggressive sales culture in the 1980s and 1990s. Larry Ellison, the founder of Oracle, famously encouraged his sales teams to do whatever it took to close deals. This led to some pretty outrageous tactics, including sales reps camping out in clients’ lobbies until they secured a signature. One story that has become almost legendary involves an Oracle sales rep who supposedly rented out a billboard near a client’s office, with a message directly addressing the CEO and urging them to sign the contract .
Today, technology has smoothed out many of those rough edges—no more begging customers to find a fax machine or surprising executives with a cake (although maybe we should try that!) But the determination to close the deal, no matter the obstacles, remains the same. It’s this tenacity that defines the best in the business, whether you’re working in the cloud or pounding the pavement.
Now, I’d love to hear from you. What’s the most ridiculous thing you’ve done to get an order signed? Share your story in the comments below—after all, every seasoned salesperson has a tale worth telling.