Sales Story

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A Sales Story

Let’s start with some background.

We’re Not in Hollywood

If you stick with selling long enough, you’ll eventually get a chance to pitch your first really big deal. Perhaps it promises huge revenue, or has strategic importance for the company, or it involves an important presentation to a room of senior executives, or just has the potential to really blow out the comp plan. Whatever the circumstances, it’s a simultaneously thrilling and humbling experience, and when you’re in the midst of such a deal it can feel truly overwhelming. But it can also offer a moment of clarity, because you come face-to-face with the realization that being a professional salesperson is either just a job or, hopefully, something much bigger.

My first significant sales opportunity had all of the above ingredients. It was big (relatively speaking), amounting to about thirty percent of my quota. It was lucrative, in that it would put me over quota and into some attractive accelerators. It was strategic to the company as it would set us up as the standard database software and programming tools for the client organization, which meant a big dog-and-pony presentation before any purchase decision could occur. Plus, it all had to get done by midnight on December 31st. (One of the odd realities of working for a public company is the arbitrary deadline of the fiscal year end.)


The Complexities of an Enterprise Sale

To get this deal closed, we needed to set up a detailed technical presentation and proposal discussion with a key executive director of this Fortune Ten company. This particular executive had signing authority for millions of dollars, had a global organization with over 10,000 people reporting up through him, and had a well-deserved reputation for being impatient, demanding, and painfully blunt. We needed a commitment by the middle of December if we were going to get all the paperwork done and the deal closed and booked.

It wasn’t easy. After what seemed like a never-ending coordination campaign, juggling calendars to make sure all the right people were available, we had a date set: 5:00pm on a Thursday one week before Christmas. I spent weeks leading up to this big event editing and updating slide decks and proposals, both internally and with my day-to-day contact. I also spent hours fine-tuning the value proposition, addressing the potential obstacles and outlining the technical support structure.

Every day seemed to uncover some new problem or concern. An inexplicable bug turned up in the software that caused their system to hang. One of the client’s engineers had an intense encounter with our tech support team. Their team of attorneys raised possible deal-killing licensing issues. AS these piled up, the likelihood of the big pitch meeting was looking less encouraging with each passing day.

Truthfully, I’d started to hope the big day would never arrive. My boss was one of those ‘hands-off, throw you into the deep end, what doesn’t kill you makes you stronger’ kind of sales managers. Which meant I owned everything start to finish. Every detail leading up to the presentation, the presentation materials, all the prep coordination, all the proposal details, and even making the presentation itself were all in the hands of someone totally out of his depth. Me.

Every aspect of this effort was new territory. I’d never structured a multi-year, global, value-added reseller proposal before. I hadn’t dealt with our headquarters on any non-standard performance thresholds. I had no prior experience working with our product management and engineering teams to influence the prioritization of specific features. Most terrifying of all, this would be my first time making a complex and financially-significant proposal presentation to a conference room filled with senior executives.


The Big Sales Presentation

Finally, that fateful Thursday in December arrived. My boss and I were at the client’s headquarters well before 5 pm to wait, first in the main lobby before being greeted and ushered up so we could then wait in the boardroom. The room itself seemed to intensify the already crippling dread that had been building in me over the last several days. It was a huge and imposing space, with impressive paneling, automatic shades to close off the view, projection screens that would lower from the ceiling with the touch of a button, and dozens of expensive chairs surrounding a table the size of a respectable boat.

My nervous pacing, paper shuffling and various other tics must have been noticeable to my otherwise detached boss, causing him to smile and let out a small chuckle. “You know,” he said with some mild amusement, “there will be a day when you look back on this as just the first of many multi-million-dollar deals in your career.” I don’t remember how I responded, if at all, because it was then that my client and several members of his team poured into the boardroom, greeted us quickly and then explained that the executive director was running late and that we should get started.

After quick pleasantries and determining the appropriate seating arrangement in such an oversized room, I launched into the presentation in a rushed but semi-competent manner.

About ten minutes into my presentation, the executive director swept into the room with a serious flourish, grabbed one of the many extra handouts set out ahead of time, and headed for what must have been his usual seat near the far end of the table. I stopped. The room became heavy and still, which prompted him to raise his hand in a rolling gesture and say “Keep going.” This was a practice he was evidently accustomed to. He then turned his attention back to the handout and proceeded to page his way through.


Getting Executive Attention

I did as I was instructed, my presentation now lurching along even more nervously than before, but only until it was interrupted a few short minutes later. The executive director unceremoniously collected his handout, got up from his seat, glanced quickly at my main contact with a look that I couldn’t interpret and swept out as briskly as he had arrived.

I completed the remaining slides with a feeling not unlike being down twenty points in the big game with three minutes left, the win impossibly out of reach but the clock still needing to be played out. When we finally wrapped up the meeting, it was with the standard platitudes and perfunctory post-game conversation, except that I had no idea if we’d won or lost. But from where I was standing, it definitely felt like defeat.

Because it was now Thursday evening and my client wouldn’t speak with the executive director until the following week, the impending doom would cloud the weekend. We could do nothing but wait for the inevitable bad news. So we waited. Until December 30th, when the office fax machine buzzed to life with a purchase order that reflected exactly the proposal terms we’d made in the presentation.

It was several weeks later, after the holidays passed and we were well into the new project, when my client explained what happened. The meeting was a formality, a required milestone after all the real work had been done. He explained casually that the decision was essentially made days prior, the team and senior management having been made comfortable with the deal and confident in their vendor selection as a result of the run-up to the meeting. It turned out the executive director had already seen the presentation, perhaps even a better delivered version, so why sit through it again? We’d already won. We just didn’t know it. (Or at least I didn’t.) No fanfare or big reveal. Anti-climactic.


Building Trust Over Time

My reaction was mostly surprise, tinged with a mild sense of anger that I’d gone through weeks of preparation, angst and self-doubt for nothing. Just think of the time and effort saved if they’d been transparent about the process. Maybe I expected that the meeting would wrap up with a dramatic close, after which the executive director would clear his throat and say, “Excellent! Let’s get going with this right away,” followed by handshakes, vigorous back-slapping and congratulations.

Of course, that would have been the wrong lesson to take away. Yes, any good story benefits from a big finish, something with lots of noise and excitement and revelation. But that’s Hollywood. If this experience taught me anything, it’s that real life and real sales situations generally don’t work like that.

Rather, it’s keeping up the grind. Executing on the fundamentals. Continuing to show up. Adding to your set of skills. Giving serious thought to what you do and how you do it. Day after day refining your craft.

Which isn’t a bad thing. It just means that all the worry and fear is wasted energy, and the mundane day-in, day-out stuff may not feel like you’re living inside a major motion picture. But that doesn’t mean it won’t have its dramatic moments.

You just want to be ready when they happen.

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