Why a Career in Enterprise Sales is Awesome!

Berkeley Kershisnik
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Published in
4 min readDec 10, 2020

The following is adapted from David Perry’s, Game of Sales; available now on Amazon.

Our society offers a nearly infinite number of choices to earn a respectable living — accountant, web designer, greeting card writer, you name it. Yet I would argue that no career offers the same potential for reward, freedom, and excitement as one in sales.

While everyone knows that sales can be exciting and financially lucrative (outside of executive leadership, the highest earners at most companies are the top salespeople), not everyone understands how it can provide so much more than that.

Especially now, with COVID-19 still severely impacting our nation’s physical and economic health, one of the biggest reasons a career in enterprise sales is awesome is that marketability is rarely a concern in this profession. Sales skills are always in demand, so with a career in enterprise sales, that means you’re in demand too.

The Problem of Portability

My route to sales was not a straight line. 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 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, though, 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 skill sets 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 skill set 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.

Ultimate Marketability

At that moment, 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.

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.

Your Ticket to Success

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.

Whatever path you choose, the skills you build will retain value as you move from one company to another. There is no such thing as job security anymore, but sales is extremely portable and allows you to make yourself indispensably valuable.

For more advice on a career in enterprise sales, you can find Game of Sales on Amazon.

David Perry advises world-class brands on how to transform their marketing organizations through the acquisition and effective use of enterprise technology solutions. Since 1999, David has worked with more than 100 companies across a wide range of industries including financial services, consumer products, technology, and healthcare. In the process, he’s driven over $125 million in new business and managed revenues. In addition to his work, David serves as a startup advisor and investor, and organizes technology entrepreneurship events in New York City. David received his MBA from the Johnson Graduate School of Management at Cornell University and lives in New York City with his wife, Arianne, and their son, James.

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