By now, you’ve probably seen the two articles Rob and I 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 by Rob
4 (More) Reasons to Consider a Career in Software Sales by Casey
With all of the positives both Rob and I 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.
Take some time to read through my four least favorite parts of the job and feel free to email me if you have questions!
1.Stress
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 [email protected] if you have any questions/comments.
“How (and why) to Start a Career in Software Sales” now available on Amazon! -
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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