Software Sales – 7 Key Steps to Break in and Succeed

Illustration of a man in a software sales role.

Software sales has got to be one of the sexiest fields for any confident salesperson to consider.

The industry is exciting and evolves faster than almost any other on the planet.

If you like the idea of selling real solutions to problems through the futuristic lens of technology, and enjoy the challenge of constant change, a software sales career path is worth considering.

If you don’t know how to kick-start your journey in software sales, it can seem like an uphill battle.

Generally speaking, you need some sales experience (although this isn’t mandatory), and the capacity to learn complex, abstract concepts.

On top of that, you need the confidence to position those concepts to potential customers, and the willingness to keep learning as your solutions evolve, or as you change jobs.

The rewards though, are definitely worth it. Successful software salespeople are some of the highest-paid employees in any industry, making 6 and even 7 figures per year.

Illustration of a salesman noticing a pile of money as he walks.

If a software sales career is starting to sound intriguing to you, keep reading.

What is Software Sales All About?

Software programs operate computers and other technology hardware, to execute specific tasks.

For most of us that aren’t IT people or developers, software is a confusing concept that we understand through our experiences using it.

As a software sales rep, it’s your responsibility to lead the sales process and position features, capabilities, and benefits to prospective customers.

For many, this is a daunting task due to the abstract nature of software. Many sales professionals are more comfortable selling tangible products or services.

If you’re intrigued by software and technology you probably know this is an area you want to explore.

So the first tip is to trust your gut and believe in your ability to become a successful software sales representative.

How Do You Break in and Succeed in Software Sales?

First things first, you need to do some self-checks about where to start.

Then you need to get your foot in the door with a few available software sales jobs.

Finally, once you land that ideal gig, you need a few strategies to get on the path to rapid success.

Let’s get started with the 7 key steps!

1. Assess Your Technical Acumen

Before you get too far, pause and be realistic about your level of technical expertise, and your willingness to improve it.

This doesn’t mean that you need to be a coding whiz or an algorithm expert. Instead, it’s about your capacity to comprehend different types of business software to the degree you will need in order to sell it.

Do terms like middleware, database, and security resonate with you?

Or are front-end and back-office applications more in line with your skillset?

The latter often suits non-technical salespeople better, but don’t let that deter you if technology isn’t quite second nature yet.

Your comfort zone can expand through continuous learning, so if something intrigues you, dig in and learn about it.

2. Pick a Sub-Sector and Companies to Target

The software industry is a broad spectrum, teeming with sub-sectors.

Consider all the software programs required to run everything from computers to phones, TV’s to cars, tech clouds to network equipment, and beyond.

Each of these subsectors features advantages and challenges that can significantly shape your work as a sales rep.

What are the Main Software Sub-Sectors?

The main sub-sectors include:

  • Applications – these include both front and back-office software, like customer relationship management (CRM), supply chain management (SCM), and communication tools.
Illustration of a man presenting software applications.
  • Middleware – these programs bridge different applications and allow for information exchange.
  • Database, Storage, and Security – tools that organize, manage and protect data.
Illustration of a woman presenting security solutions.
  • Networking and Infrastructure – programs that operate internal and cloud network environments.
Illustration of a woman presenting networking solutions.
  • New and Emerging Categories – All of the above sub-sectors continue to evolve, and new tools emerge constantly including business process management, mobile tools, AI, etc.
Illustration of a man presenting mobile solutions.

Company Related Considerations

Once you know the type of software you are interested in, next consider what types of companies are a match for your skillset and interests.

Do you gravitate towards lean start-ups that have less structure and systems, but may be more aligned with recent industry trends.

Perhaps you prefer an established corporate environment with exceptional onboarding and an established sales team.

Maybe something in the middle feels right for you, if there is a high quality sales manager.

Think it through and outline a list of preferred characteristics.

Learn more about company size and type here.

3. What Type of Role is Best for You?

Because this industry is more complex and challenging than most, software sales jobs often require previous sales experience.

However, this isn’t an absolute rule.

Many software companies will bring on a sales development representative or inside sales specialist straight out of college, so long as they fit the personality profile.

If you do have previous sales experience, you probably already know if you are a hunter or a farmer.

You may have a clear sense of the types of software sales jobs you are most qualified for. If not, check out this extensive description of the 5 main non-managerial professional sales roles that are available in the software industry.

The last thing you want to understand is the deal sizes you are comfortable with… but also remember, nobody started out selling 6 or 7-figure deals.

Believe that you can work up to larger deal sizes as you gain experience along your software sales career path.

4. Go Find the Job!

Now it’s getting fun! You know what you can handle, you know the companies you are most interested in, and you know the roles you want.

Time to start scanning company websites and job boards like Indeed, and combing your existing network on LinkedIn.

Illustration of a person accessing their network to help them land a software sales job.

Sales teams are changing all the time in this fast paced industry, so opportunities are everywhere.

Find the sales leaders, sales managers, and hiring managers that are your gateway to the companies and jobs you most covet. 

Approach them warm if you can (through a contact introduction) or cold if you must. Hey, you’re in sales so a well-crafted cold approach could be just the tactic you need!

Do you know any inside or outside sales reps, sales engineers or sales managers in the industry that you could call on for help?

Check out this article for more tips on networking, hunting, and approaching people to land the job you desire.

Once You’re in front of the Hiring Manager

Now it’s time to shine and leverage your sales skills to leapfrog the competition.

Illustration of a woman in a hiring manager role, sitting in an office chair.

What sets you apart from others.

Talk about your commitment, work rate, and good habits.

If you’re lacking experience, make them know why you’re a good bet anyways.

Be prepared to answer their toughest questions by planning in advance. Have stories to tell and weave narratives into your answers.

Come equipped with questions of your own.

Don’t hide your displeasure with any aspects of the offering. Nobody wants a yes-man or yes-woman.

Crushing an interview isn’t hard if you take it seriously and come in prepared. If it doesn’t go your way, take the L and learn something for your next interview at bat.

5. Commit to Learning Your Solutions

So you landed the gig?! Congratulations!!

Illustration of a business man celebrating getting a software sales job.

Now it’s time to prove that you are an asset to your new employer.

Invest all your energy and focus into absorbing what you are learning during onboarding.

Invest extra time learning about how your products and services are positioned on the corporate website and marketing materials.

Get demo account access and start using your new products. Don’t forget to leverage help systems and training resources that customers have access to.

Review the product roadmap and historical release notes to learn how the software is evolving.

Schedule time with sales team members and other colleagues across relevant departments that can help, and liaise with your sales manager often.

Be unrelenting!!

6. Advance Your Sales Skills as Fast as Possible!

I don’t care how long you have been in the game of sales, you need to remain a student so you can keep improving.

Sadly, only a tiny fraction of software sales representatives make career and skills development a priority.

If you’re not reading books, listening to podcasts, reviewing email newsletters, and discussing skills with your professional and work colleagues, you are not fully committed to software sales success.

Start with this list of selling skills and commit to ongoing growth today.

7. Improve Your Daily Habits

A great software sales manager once told me, “show me your habits and I’ll show you your future.”

Everything you are today, is a byproduct of yesterday’s habits.

Everything you will become tomorrow will be a result of your habits today.

That goes for your personal life and your professional life.

Are you on time each day? Are you focused or distracted? How do you structure your day? Do you knock off everything you are committed to doing? Do you prospect regularly?

The Golden Nugget

The best advice in this entire article is to take control of ALL your daily habits and begin living an intentional life of your choosing, regardless of how you feel each day.

Your behavior must shift from circumstantial to non-negotiable if you want true success. 

Begin instilling the right sales behaviors and habits immediately and never waiver.

Software Sales FAQs

Is software sales more difficult than other types of sales?

The short answer is “yes”, software is more complex to learn and master than many other product types.

However, you don’t need a Ph.D. or an IQ above 120 to sell software.

All you need is curiosity, willingness to learn, and confidence you can become successful.

Is software sales a growing industry?

Absolutely. With the increasing reliance on technology for business operations and consumer life, the demand for most types of software is steadily rising.

Is there good money in software sales?

The earning potential in software sales can be substantial. Compensation in most cases includes a base salary, commissions based on performance, plus good benefits. In start-up environments, there may even be an opportunity for equity.

Illustration of a business woman with progressively larger piles of money in front of her.

Is a degree required for software sales?

Some companies will require a degree, but many will accept salespeople with a solid track record. Relevant degrees include business, marketing, psychology, or technical fields such as computer science (for sales engineers).

Illustration of a woman graduating university with a degree in hand.

Never let the requirement for a degree stop you from trying. You never know what concessions could be made if you have the right stuff.


Software sales is an exciting field that includes more challenges than many industries, but conversely features many incredible rewards.

If you like exciting, cutting-edge products that can make a massive impact on customer organizations, software sales is a road worth traveling.

Illustration of a business man walking along a winding road.

If you like an ever-evolving industry that never stagnates, software is an incredible place to be.

When you’re ready to make the move, follow the steps in this article, and don’t take no for an answer!

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