Four reasons NOT to start a career in Software Sales

By now, you’ve probably seen the two articles we have written advocating for Software Sales Careers. If you haven’t yet, check them out below.

4 Reasons to Consider a Career in Software Sales

4 (More) Reasons to Consider a Career in Software Sales

With all of the positives we see with Software Sales Careers, that’s not to say there aren’t some major drawbacks to the career. Rather than waste a couple of years of your life just to figure out that this career path isn’t for you, my goal with this article is to let you know that it isn’t all huge money and happy hours.

My name is James a software sales veteran who is now a member of the resume writing team here at

Take some time to read through what were my four least favorite parts of the job and feel free to post a comment below if you have questions!


Some people can deal with stress and some people cannot. Personally, after playing sports my whole life and starting my own business, I thought I would be accustomed to it. However, software sales is a totally different type of non-stop stress that I never could have prepared myself for.

Your job is incredibly transparent. I mean really really transparent. As in, there is a leaderboard that basically anyone has access to. Remember before when I said sales is a great way to get recognized by leadership? Well it’s always a great way to get recognized by leadership for the wrong reasons.

If you have a bad quarter you could be just a couple of months away from losing your job. Personally, I do not have a family I support yet, but I couldn’t imagine being in that situation with a couple of kids at home who depend on your commission check.

I guess what I’m trying to say is there is definitely a trade off that you’re making in order to get the higher pay checks. That trade off, for me, was basically my sanity as I was always thinking about how close I was to quota. Some people feed off of this and love it, while others are crippled by it and it takes over their lives. I guess you’ll have to find out for yourself which one you are.

2.It’s a grind

Now don’t get me wrong, there are some sales roles that are pretty cush. I’m talking wining and dining, golfing on a Tuesday and taking a client to a ball game. However, considering you’re reading this I’d assume you’re not quite there yet and your first job is going to be a bit more of a grind.

What do I mean when I say grind?

I mean you’re probably going to have to pick up the phone and call 50-150 prospects a day with the hope that maybe 3-5 of them give you more than a minute of their time. You’re going to be emailing people every waking minute. And my personal kryptonite, you’re going to be scouring the internet trying to find the correct contact at a company and what their personal email may be. Did I mention that you’re going to be doing this every single day for an extended period of time?

This an incredibly desirable job, but you definitely have to pay your dues to get there.

3. Quota never stops

As mentioned previously, there are a number of ways your commission could be paid out (monthly, quarterly, annually). For quota, it’s the same way and for an entry-level job that means you’re probably on a shorter leash (meaning monthly or quarterly).

For instance, at LinkedIn in our “Sales Development” role their core job was just to set up meetings for the Account Executives. So every day they would come in to cold call, email and send InMails (via LinkedIn) to try to get prospects interested enough to take a full 30 minute call with the Account Executive. They had to schedule usually around 50 a month. Since most of them didn’t hit that number until the last week of the month that means they had little to no time before that number dropped back to zero and they needed to restart.

Quota with a monetary value is the same. As an Account Executive I may need to close 200k of new business a quarter, which means it goes back to $0 on January 1st, April 1st, July 1st and October 1st. There is no worse feeling in the world than that.

4.You’re always on

Let me tell you a quick story. It was Christmas Day 2014 and LinkedIn was basically shut down for the year. I had flown home to Camas, Washington and should have been enjoying the time with my family. Everyone was at my Grandparent’s house, in fact. Well I was there too, except I was in the corner furiously writing emails on my phone and trying to close the last of my business before the New Year.

This is the life of many sales reps.

Want to take a vacation out of the country? Don’t forget to bring your computer. In this line of work you almost always need to be on (unless you have an amazing manager) because the sales process is so intricate that it’s incredibly difficult for somebody else to jump in and help you out.

At the end of the day sales has been amazing for me and I couldn’t be happier that I decided to give it a shot. It allowed me to live in San Francisco and New York City, live a lifestyle I never thought possible and make more money than I ever thought I would make. But with any job there are drawbacks, and I hope this article sheds some light on some of them.

As always, you’re welcome to drop me a note at if you have any questions/comments.

Software Sales is a fantastic career path, but it’s not for everyone. You obviously have some level of interest in the field, otherwise you wouldn’t be reading this page.

Maybe you’ve heard stories about Software Sales professionals bringing home fat paychecks, maybe your friends have recommended you check out the field.

But that type of information is usually surface level. Do you really know WHY you want to start a career in Software Sales?

Do you really know the benefits of a Software Sales career path and how it compares to your current career or other opportunities you’re considering? Perhaps you’re nervous about some of the “cons” of the industry.

Well, that’s exactly why we created these Free video resources

What you learn during the through the use of our video guides:

  • How compensation is structured
  • Career Progression opportunities
  • What my favorite parts of Software Sales are
  • What my least favorite parts of Sales Sales are

Whether you have experience in your chosen career or not, we can write you the perfect interview catching sales resume. If you would like to beat the competition in the lucrative industry of sales then head over to our homepage and order a professionally written sales resume done by veterans of the sales industry. Career Dreaming Resume Packs

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