A Few Tips on How to Break Into Tech Sales

If you are a veteran who has overcome the stigma that a career in sales is cheap, dirty and beneath you, then please skip to the next paragraph. If you still have doubts, listen up. Your life probably looks a lot different than it did when you raised your right hand many years ago. The world looks different, too, thanks to you and others like you. But now you are looking for a change. Maybe you’ve decided that you want greater schedule control or a role that puts you in daily contact with business and government leaders that are transforming the world. Maybe it’s salary related, or maybe you just want a new challenge. Your reasons are your own. Working in fast growing industries, such as cloud technology or biotech, can be exciting and taking a role in sales gives you a platform to deliver real solutions and help companies grow. Certain industries continue to be white hot and offer highly lucrative and merit-based compensation to successful sales people (just a fancy way of saying you can make a lot of dough if you’re good). Furthermore, as a sales leader you are the quarterback. You coordinate multimillion dollar deals, lead strategy sessions with executives and have a seat at the table where decisions are made. For those that seek a challenge, read on.

If you are interested in entering the field of B2B sales or are looking to improve your skills, this article outlines some key insights from the Challenger Selling Model and how a new era of sales strategy may be on the horizon. Moreover, you can be confident that your time in the military has been a perfect primer to acquire key skills and experiences to complement the Challenger Selling Model.

Perhaps you’ve heard the phrase, “It’s all about how you sell, not what you sell.” The Challenger Selling Model parallels a trend that sees sales reps moving away from selling products and toward selling solutions. Rather than reacting to purchase orders, they take up positions as trusted advisers. Rather than having strong product knowledge, they work hard to assert themselves as high-level strategic visionaries. The best sales reps are the ones that will not rest until the customer is satisfied – until they have it all.

“You don’t want most of it, you want all of it. And I won’t stop until you get all of it”.

-Don Draper on Business

But what makes them the best? Traditionally, self-selected sales professionals have above average interpersonal skills and are efficient at building relationships with clients. They have a strong work ethic and are reactive to the needs and problems of their customers. But what separates top performers from the average performers? The research upon which the break into tech salesChallenger Selling Model (from the Corporate Executive Board) is founded finds that a very specific bundle of traits are responsible for a massive performance gap in sales organizations. This grouping of traits is dominant in the star performers called Challengers.

A Challenger can very simply be defined as a sales leader that can teach, tailor and take control while maintaining a healthy level of constructive tension. Surprised? So were top sales executives when they analyzed the research. This radical departure from how sales executives have traditionally approached driving sales is creating a disruptive innovation, and an opportunity for transitioning veterans, in the field of sales. I’ll spend the remainder of the article diving deeper into a few of these traits and how military veterans fall naturally into them.


Challengers bring with them unique perspectives on a customer’s business. They have the confidence and forehandedness to engage customers in pursuit of the best way forward. They serve as advisers and have the ability to teach for differentiation throughout the sales process. Often, the greatest problem a customer has is not knowing what their problem is, which is why so much time is spent doing discovery work. Challengers acknowledge this and take a different approach by teaching customers what they are doing wrong and how they can fix it. Conversely, military veterans, enlisted and officers alike, are great team players who thrive (and survive) based on their ability to communicate quickly and efficiently. Constant debriefing and prebriefing sessions give veterans valuable collaboration and communication skills that translate to Corporate America well. Every servicemember is taught to be both a teacher and a student. Additionally, many veterans come off of active duty with experience leading students or recruits as instructors.

Take Control

Challengers are superior at beating a winning battle rhythm into sales cycles by focusing on what’s ahead. They are confident in the value they are delivering and are not afraid to talk openly about pricing. Challengers are also experts at creating momentum and avoiding the dreaded “no-decision”. You may be surprised to hear that many customers simply don’t know how to buy and what they really need is some good old-fashioned leadership. This is where veterans can really shine. They have led and been led under circumstances the average non-veteran cannot imagine. They’ve experienced good and bad leaders and took mental notes of what was effective and what wasn’t. In the process, they’ve developed a leadership profile. All veterans bring some level of tried-and-true leadership to the table. Furthermore, transitioning veterans know that this will be their primary strength and will therefore be more likely to flex it.

For sales organizations, if you aren’t hiring Challenger reps, chances are you will be scratching your head over why you keep coming up short as the complexity of your deals increases. Moreover, if you have found that Challengers fit nicely into your organization, you may want to look to the veteran community for your next star sales performer.

More information on the Challenger Sales Model can be found by visiting www.executiveboard.com.