Chapter 1

1. Why Enterprise Sales Is Awesome!

“Choose a job you love, and you will never have to work a day in your life.”

—Confucius (ancient philosopher, teacher, and politician)

Our society offers a nearly infinite number of choices to earn a respectable living. You could be an accountant, web designer, greeting card writer, stunt double, etc. I would argue that none of those professions, however, offer the same potential for reward, freedom, and excitement as a career in sales. Okay, maybe being a stunt double is more exciting than sales, but there’s significantly more risk involved with that as a career choice.

My route to sales was not a straight line. Fortunately, my background in other key functional areas such as business analysis and consulting showed me just how great a career in sales could really be.

Although I’ve always gravitated toward the revenue generating side of business, I began my career as an analyst and consultant. During that phase of my professional life, I recall a pivotal moment that steered me toward the path of sales.

At the time, I was working with a business analyst and programmer who was absolutely brilliant. He learned our company’s proprietary development language inside and out to create an extremely useful and unique piece of mapping software. The program enabled our company to translate data sources seamlessly, to create consolidated financial reporting for ultra-high-net-worth individuals and top institutions. The achievement was nothing short of amazing, and it became the foundation for a $100 million revenue stream for the company.

From an individual career perspective, I thought there was a big problem with that situation—lack of portability. That guy’s talent was undeniable and his contribution to the company’s bottom line was stupendous. But once he built that software, he was expendable, as his work was finished. From that point forward, programmers with much lesser skillsets could maintain everything, and he couldn’t take any of his hard work with him because everything he built was in an obscure internal-only programming language, tied to esoteric systems with highly specialized use. That caused me to reflect on my own situation.

As a business analyst, I was in a similar position. I couldn’t take my skillset with me to another company, and if I created a similar $100 million revenue stream, I wouldn’t get to participate in the upside.

That particular organization was also in the midst of being acquired, so we were going through several rounds of layoffs, which made me realize that the idea of job security was beginning to vanish; a suspicion that, since then, has fully evolved into a stark reality of today’s economy.

At that moment, however, I decided that I didn’t want to be subject to the volatility of a potentially unstable profession any longer, and I made the commitment to choose a much more portable career path; one where I could develop a skill set that wouldn’t lose all value when I left a particular role.

Ultimate Marketability

I wanted to work in an industry where my skills would be more marketable from one company to the next. If the days of a twenty-year career with a singular organization were over—as popular opinion told us, even back in the early 2000s—it only makes sense to have a career that would allow you to flow seamlessly between opportunities, while building upon previous successes. That was the biggest factor in my decision to embark on a sales career in the first place. I soon realized that companies of all types and sizes in all industries are on the sales table. It’s a profession that provides ultimate marketability.

Sales allows people to move from one opportunity to the next without any crippling fear of extended joblessness. In a worst-case scenario, you could find yourself in a company that isn’t a good fit—for whatever reason—and you need to leave. As long as you’re committed to success, you’ll soon land another role. In fact, if you’ve demonstrated an aptitude for selling, you’ll have multiple offers from other companies lined up, perhaps before you depart.

The bottom line is, if you are committed to your craft, and have the desire to create revenue for a company, sales will allow you to write your own ticket.

Large Versus Small Companies: The Choice Is Yours

Sales can take you anywhere you want to go. You can live in the high-visibility, fast-paced world of enterprise sales and close megadeals for the most impactful companies of our time, like Adobe, Amazon, Google, and IBM. Or you could sell for a much smaller company where your performance will have a much larger impact on the overall success of the organization. If neither of those options ramp up your meter for career excitement enough, perhaps you’ll become the Chief Revenue Officer of a start-up or even create your own company, where you can build something from nothing and watch it grow.

Understand that smaller companies may not have the budget to send the entire workforce to Las Vegas for an all-expenses-paid, weekend-long festival of fun. However, you most likely will have the opportunity to partner with bigger companies and attend their sales kick-offs and customer conferences, as well as other high-profile industry events.

If you work in sales, at a large or small company, the sky is the limit, but know that what happens in Vegas doesn’t necessarily stay in Vegas when you’re there with 2,000 coworkers.

Take a look at the table below for a typical listing of the differing benefits from working at large or small companies. Then, decide which one suits you best. Also, don’t be afraid to try a small company for now and a large one later, or vice-versa. You might have to experience both options before you know which one you prefer.

The Benefits of a Career in Sales at Large vs. Small Companies

Game Changer #1: Enterprise sales is an elite profession with significant lateral and upward mobility. Outside of executive leadership, the highest earners at most companies, large and small, are the top salespeople.

It’s a Wonderful Life

A career in sales means much more than having a highly marketable skillset. It also means that you’re going to have access to some of the most incredible experiences the world has to offer, especially if you choose to work in enterprise technology sales. How many other professions offer these benefits?

• If you like to travel, a career in sales is a no-brainer. Conferences and vacations are just one form of the travel involved. You could—and likely will—travel all over the country and even the world—depending on your role—to visit clients, partners, and other key players involved in various deals.
• Sales allows you to build a powerful and expansive network, consisting of some of the most influential and high-profile executives in the world. Better yet, the value of that network grows over time, as your peers and clients break off into different companies.
• Opportunities to refine and master your craft will be present throughout your career. As such, deals will become easier to close and bigger deals become more doable. Eventually, mega-deals begin to surface and from there, anything is possible!
• Unlike a career in law or consulting, you’re not trading time for money in sales. The two assets are not directly exchangeable. Instead, the more skilled you become at your craft, the less time it takes to close deals. Soon enough, you’ll learn how to make more money in less time than you ever thought possible. A meeting over coffee or a chance encounter at a conference could lead to a transformational deal and change...