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Four (more) reasons you should consider a career in Software Sales

November 15, 2023 by Casey Leave a Comment

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Even more reasons to consider a Software Sales Career

Rob wrote a great piece a little over a year ago regarding why you should consider a career in Software Sales. Before reading my post be sure to check his out first as I’m not going to be repeating:

“4 Reasons to Consider a Career in Software Sales”

For me I knew that software sales wasn’t going to be my lifelong career. I’ve always known that I wanted to get back into entrepreneurship so my reasons for getting into the career were probably a lot different than others may have been.

1.It’s a great way to get your foot in the door

Like many of you reading I did not go to a top tier University (although I definitely loved my time at Western Washington), I did not have family connections and I sure as shit didn’t have money to take unpaid internships as a way to get noticed. In fact, to make matters worse I went to school about an hour North of Seattle and I desperately wanted to find work in the San Francisco Bay Area. So how was I able to get a job at my dream company in 2012 when I really shouldn’t have been considered?

I took a job in sales. Not just in sales, but in Sales Development.

Sales development is a grind and probably what most people imagine when they think of “sales”. It was 100 calls a day with people who normally didn’t want to talk to me. It wasn’t great, but after eight months of doing it I had opportunities to move into almost any part of LinkedIn that I wanted to (marketing, ops, product, etc). In addition, other companies were willing to look at me for jobs in, say marketing, that I never would have been qualified for previously without LinkedIn on my profile.

Long story short, it’s a great way to get your foot in the door at a company you really want to work at even if it isn’t your dream job.

2. You learn a lot

Hands down my favorite part about selling has been the executives I had the opportunity to have interactions with. So lets fast forward past the cold call, the hang ups and the people mad you interrupted their family dinner. Lets get to the point where somebody is actually interested in your product. If you’re doing your job right, regardless of the product/service you’re selling, you should be speaking to an executive (Director, Vice President, C-Level).

The good sales professionals need to understand their prospect’s business and business needs before they can make a true recommendation of what that prospect should be buying. This is as good as it gets for somebody who is an aspiring entrepreneur, or just somebody generally interested in how business decisions are made.

This is when you have the chance to ask that executive what their personal targets are, how they make decisions and best yet, how they expect to reach their goals. This is when you get to push back on their assumptions, ask what is going right/wrong and my personal favorite, what happens to the company if…?

In what other career path would you have the opportunity to challenge an executive’s thinking (respectfully), and get a glimpse into the inner workings of how they think?

3. Internal exposure

If you’re working at a company of 50 people or less than this probably isn’t important, but when you get to a company with hundreds or thousands of people it can become incredibly difficult for anyone to get the ear of the CEO. The time of an executive, specifically at the VP or C-level, becomes so important that it can literally become impossible to get on their radar.

You know what will get on their radar? Closing one of the biggest deals in your company’s history.

Not only is the pay great (see Rob’s post), but you will have a direct line to basically anybody at your company you want. Not your manager taking credit for your work, or support helping you cross the finish line. We’re talking about you personally, and everybody knowing that you’re the one who got it done.

4. Something different every day

To explain what I mean here I need to give you a glimpse into my job at LinkedIn. The reason LinkedIn is a valuable recruitment tool is because there are millions of people on there who are not actively looking for a job (so they won’t be on a job board), but they would be interested in a new job opportunity if it was placed in front of them. So it gives recruiters access to a pool of candidates who before LinkedIn were impossible to find. As sales people there we sold a number of solutions to help those recruiters use the network more efficiently to recruit. Got it?

The reason I bring this up is because it seems like you would do the same thing every day, right? Just explain how the platform works and have people sign up. Same pitch all the time. Well not exactly.

We were selling this solution to companies across every industry imaginable and into every job function withn those industries. That means there are literally hundreds of different reasons why somebody would want it and thousands of different ways it could effect a business. Do you get where I’m going with this?

That means every day I spoke to someone in a different industry, with different needs, who was buying our services for a totally different reason. I’m not saying after software sales role is like that, but many of them are.

What’d you think of my list? Feel free to drop me a note at [email protected] if you have any questions or have anything else on your mind.

Ready to take the next step? Take my FREE, 5-Day Software Sales Challenge

Take the 5-Day Challenge

Are you on the fence when it comes to pursuing a career in Software Sales? Well, if so, I put together a FREE 5-Day Challenge just for you.

This quick challenge is designed to walk you through the positives and negatives of a career in Software Sales, to help you quickly evaluate whether or not this industry is for you.

Over a period of 5 days, I provide my own structured opinions on the Software Sales field, how compensation is structured, career progression opportunities and even the toughest parts about the job.

This 5 Day Challenge is designed to be a quick glimpse into the world of software sales, so you can easily make a determination about your fit in this industry.

Before you take the time required to land a job in software sales, figure out if this is really a career path for you.

I look forward to walking you through potential career opportunities in this space and helping you determine whether or not this is a path for you.

Interested in learning more, check out the new course by clicking the button below!

Take the 5 Day Software Sales Challenge

“How (and why) to Start a Career in Software Sales” now available on Amazon! -

How (and why) to Start a Career in Software Sales available now!

My new book, entitled “How (and why) to Start a Career in Software Sales”, is now available for purchase on Amazon Kindle and Paperback! My goal is to answer the questions that I’ve been asked on a consistent basis, discuss the positives (and negatives) regarding a career in software in sales and outline a clear guide to getting started in the profession.

The book, which was released May 2nd, 2016, has received fantastic feedback some far from readers of all experience levels and backgrounds. Just take for example what reader Alex sent to me after reading the book via email!

“Hey Rob, Just wanted to follow up after reading your book. I binge read the whole thing in an hour. I couldn’t get enough of it and just kept turning the pages. After reading through your posts on the website combined with reading the book, I am confident that a career in software sales is something that I would love pursue.” - Alex

Want to read the book’s first chapter? Click below

If you’d like to take a read through the first chapter of “How and Why to Start a Career in Software Sales”, absolutely free, you can click on the button below for access to the content. Take a read through the first chapter and that should help you to understand if a career in software sales is something that you’d really like to pursue, then the rest of the book covers how to do it.
Click HERE for your Free Book Chapter

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"How (and why) to Start a Career in Software Sales" is available on Amazon now!
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6 Weeks Career Course Are you interested in starting a career in Software Sales, but not sure how to do it? Well, you're in the right place!

Rob has recently created the Software Sales Academy to help you to find the software sales job that you're truly looking for. Interested in learning more, check out the new course by clicking the button below!

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Hey everyone, my name is Rob and I'm an industry veteran technical recruiter and software sales professional, internet entrepreneur and disruptive technology enthusiast.

My goal as the founder of Career Dreaming is to help the 20-something year old Millennials out there find satisfying employment. By sharing my personal job search and employment experience, I hope to bring your dream career within reach.

If you need ANY advice, shoot me an email at [email protected],com or @CareerDreamin. [Read More …]

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