Career Dreaming

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Are you ready to accelerate your sales career? Join Rob Paone and Casey Mcenry as they attack career possibilities from two very unique angles

Learn more by checking out all of our content below!

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Get Rob's New Book on Amazon!

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

I'm excited to share with you that I have released a brand new book, "How (and why) to Start a Career in Software Sales", which is now available on Amazon Kindle and Paperback (obviously both Prime because free shipping is my jam). If you've ever had any interest in exploring a career in software sales and the benefits that it might provide you personally and professionally, this is the book!

To get the first chapter, "Why to Consider a Software Sales Career", delivered free to your email inbox via downloadable PDF, click the button below for instant delivery!

Click HERE for your Free Book Chapter

"6 Weeks to Start a Career in Software Sales" Course

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 and Casey have recently created this brand new course, "6 Weeks to Start a Career in Software Sales" 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!

Learn more about the Software Sales Course

Interested in a Software Sales Career?

Four reasons NOT to start a career in Software Sales

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 […]

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

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 […]

Best Sales Books - For Current and Prospective Sales Reps

Whether you’re currently in the sales profession or actively considering making a move into the space, in my opinion, these are some of the best sales books that you can read. In either stage of a career, whether you’re in the sales industry or outside of it and trying to get in, I’d recommend reading […]

Read the Latest on Career Dreaming

Four reasons NOT to start a career in Software Sales

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 […]

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

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 […]

Best Sales Books - For Current and Prospective Sales Reps

Whether you’re currently in the sales profession or actively considering making a move into the space, in my opinion, these are some of the best sales books that you can read. In either stage of a career, whether you’re in the sales industry or outside of it and trying to get in, I’d recommend reading […]

A Software Sales Interview Story - Don’t Do This!

It’s time for a little story of how I messed up big time in an interview, really big time. I was honestly about five minutes away from a job offer with a nice raise, when I screwed up to the point where all of the good things that occurred in the previous interviews were thrown […]

Ask Rob: Software Sales Questions

I’m excited to announce the beginning of a new weekly feature on Career Dreaming, the “Ask Rob - Software Sales” column, which will be posted every Wednesday. I receive a ton of emails from readers literally throughout the world, asking about topics relating to careers in the sales industry, most specifically regarding the software sales […]

The 5 Best Sales Jobs for Long-Term Success

As a software sales professional, I’m very much an advocate for long-term career prospects in the space, as well as earning potential. However, not everyone that is interested in a sales career loves the IT/software space, so I have comprised this research on the 5 best sales jobs across any industry. When examining the best sales jobs, […]

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