Is software sales a good career in 2023?

Is software sales a good career in 2023

Breaking into SaaS Sales

Over the past couple of years, friends and family have expressed interest in learning more about how not only to break into software sales but also succeed in software sales. 

I can see why they are intrigued.

The earning potential.

The flexibility to work remotely.

The career progression potential.

And of course, the allure of an equity event when the company you work for is acquired.

All of these are part of the tremendous upside associated with a career in software sales.

Why is a career in software sales so exciting? 

Most people asking about how to get into software sales come from dental hygiene, banking, fire fighting, car sales, and everything in between. 

As most people have seen, software sales is a tough gig right now.

The rewards don’t come without risk though. Especially in the tough world of venture capital-funded startups with aggressive revenue goals to hit. We’ve seen what happens when they don’t reach their goals – layoffs.

That being said, the upsides definitely outweigh the downsides of a career in software sales. 

Call coaching software sales

Take for example becoming a single-digit employee at a company operating in the sales coaching or call coaching software vertical. 

According to SEMRush, these are just two verticals that are seeing triple-digit growth in search volume. 

Why does that matter? 

It matters because it shows there is a market pull towards products that fall into these categories, prospective customers are actively looking for and wanting to buy call coaching and sales coaching software. 

Double down on that with various research studies that show the call coaching software is expected to have a compound annual growth rate (CAGR) of no less than 18% for the next five years. 

What does that mean for your career progression

It means that a motivated individual can go from SDR to AE to Manager to Director to VP – potentially even a CRO within eight to ten years when one goes all in on the right company. 

Unimaginable in most other industries.

On top of career progression, that type of career trajectory also takes one’s earning potential from the mid-five figures to the north of $300,000 in about five to six years. 

On top of just finding the right company in the right market selling the right product (sales coaching or call coaching software for example), there are a few other things one must have if one wants to win in this racket. 

Qualities to leave at the door when you start a career in software sales 

Having spent the last almost nine years in software sales, I have seen my fair share of reps not make it. 

They end up on a coaching plan, then a performance improvement plan (known as a PIP) before being let go. 

Usually, it’s about nine months into their role this happens.

The reps who make it usually have a few things in common, we have written about that before in our blog post “how to be a top 1% rep”. So let us dive into the things you should leave behind if you want to find success while pursuing a career in software sales. 

1) Check your ego and “know it all” attitude at the door. 

According to Mark Roberge, in his book The Sales Acceleration Formula, the number one thing that makes a rep successful is coachability. 

To be successful in sales, any individual needs to be constantly learning on their own. The market, buyer personas, products, and the selling cycle are all constantly changing. 

For example, in early 2023 we are seeing the CFO become more involved in software buying decisions, it is time to learn how to talk and think like an accountant. 

2) Leave the pom poms in the car. 

Ok, maybe this should actually be “leave the need to be motivated by someone else in the car”.

A career in software sales, especially in the early days as an individual contributor can be a grind. 

Even if you are at the “hot company” operating in a growing market the chances are high that the majority of your day will be spent being rejected and in the monotony of prospecting and data entry. 

If you are lucky enough to have tools like real-time call coaching software your day will be slightly less stressful, but it still will take work. To be successful, in the long term, a software sales professional must be intrinsically motivated.

10x your paycheck in five years

Starting out as an SDR, one will likely make anywhere from $40,000 to $60,000 base salary. Plus you’ll have the opportunity to earn an extra $2,000 a month in variable compensation.

Moving into an AE position, depending upon the stage and market of the company can find a base salary of anywhere from $70,000 to hundreds of thousands of dollars plus usually double that in variable compensation. 

As the progression moves one into leadership roles at the Manager and Director level, base salaries are usually in the low six figures with the potential to double that in variable compensation depending upon the success of the team. 

VPs, Senior VPs, and CROs really see their paycheck climb, sometimes approaching the half-million dollars a year mark.

No other career that either…

a) doesn’t involve playing sports professionally


b) a Doctorate degree creates that level of earning potential. 

So, join a company in a hot market (sales coaching or call coaching software hint hint), work your ass off, and within a few years change your life. 

The downside to software sales

As said before, with high risk comes high reward. You don’t get paid the big bucks at corporations the way you could at high-growth startups. 

But with that comes risks.

1) Layoffs. But as you’ve seen the startup world community is very tight and everyone is out there to help you succeed. is a resource put together by Corporate Bro and Keyplay to help with those people impacted by layoffs.

2) Lack of funding. The Venture Capital world can be cruel. Many startups don’t survive so that high reward, fast track to a VP position doesn’t come true. TechCrunch put together a great graphic to show you the curve of survival.

3) It’s freakin hard work. Startup life is not easy. You get kicked in the shins over and over again. You have to have grit and stamina to make it.

Other resources

5 Myths about SaaS Sales

Things I’ve Learned While Being an SDR

The Hardest Part of Sales

Frequently Asked Questions

Transitioning into software sales from diverse backgrounds requires a blend of adaptable skills and a willingness to learn.

While specific technical knowledge might not always be necessary, qualities such as effective communication, resilience, and a strong work ethic are highly valued.

Individuals can also benefit from seeking out opportunities for training or education in sales techniques and familiarizing themselves with the software industry’s dynamics and terminology.

Aspiring software sales professionals may encounter various challenges along their career path. These could include intense competition, rejection, and the pressure to meet aggressive sales targets.

Additionally, navigating the ever-evolving landscape of technology and understanding complex software solutions can pose significant hurdles.

To overcome these obstacles, individuals should prioritize continuous learning, seek mentorship from experienced sales professionals, and develop a resilient mindset to persevere through setbacks.