Why Sales Jobs Are So Difficult to Hire For

According to the U.S. Bureau of Labor Statistics, “sales occupations are projected to decline between 2018 and 2028,” a trend that is bound to make it more challenging for employers to hire sales associates. 

However, this prediction is just one of several reasons sales jobs are challenging to hire for. Other factors, such as technology changes, decreased appeal, and increased stigmatization also contribute to declining sales positions and qualified candidates. 

This explains why it can be so difficult to find and hire a high-performing salesperson – let alone a whole team of them. Fortunately, there are several steps sales managers can take to fill sales jobs faster with better candidates.

This guide will explore the reasons why sales jobs are so difficult to hire for in greater detail and ways for you to overcome this hiring challenge.

Why Is Sales So Difficult?

Is sales hard? Sales positions have been around for thousands of years, but that doesn’t mean they have stayed the same. 

So yes, sales is hard. Retail positions, sales, and marketing jobs have continually become more complex and fast-paced as technology and society have continued to change and diversify. 

Sales is complex as it requires employees to remain consistently up-to-date with sales trends, marketing techniques, technological innovations, and social changes. But some sales positions are more complex than others.

What Are the Hardest Sales Jobs?

The hardest sales jobs tend to be those that require an exceptional amount of creativity and social awareness. Convincing strangers to invest in a product or service that they did not necessarily ask for is tricky but not impossible.

Sales managers and seasonal sales associates may have the most challenging jobs of all sales associates. However, sales positions within start-up companies or brand-new companies can be just as demanding. 

But the worst sales jobs vary depending on your opinion and preferences. The right person may find that these positions are some of the easiest sales jobs.

Is Sales the Most Difficult Job?

Are sales jobs really that hard? Difficulty, like beauty, lies in the eye of the beholder. What may be challenging to you could be a piece of cake for someone else!

As such, sales may be one of the hardest careers to pursue for those that don’t enjoy social interactions, persuasive conversations, or cannot handle the constant rejection that naturally comes with sales. However, sales jobs could be a dream come true for individuals that are naturally gregarious, competitive, and like to challenge themselves daily.

Top 4 Reasons Sales Jobs Are So Hard to Fill in Today’s World

Sales jobs are challenging due to their fast-paced nature, constantly changing dynamics, and socialization requirements. However, due to recent social and economic changes, sales jobs are particularly hard to fill. 

But, whether your sales team is just developing or you find yourself constantly faced with high turnover in your sales department, having a well-staffed sales team is critical to building a scalable business that consistently generates enough revenue to keep your business profitable.

So, without further ado, we will explore the top four reasons why sales jobs are so challenging to hire for in today’s world and steps you can take to fill your open sales positions faster (and with better candidates).

1. Lost Appeal to Millennials

The younger generations now entering the workforce are far less keen on sales positions than their predecessors. That is because millennials and their successors (Generation Z) are far less focused on traditional sales positions. They may even find sales exploitative. 

Instead, millennials often favor other career paths that allow for more flexibility and stability. For this reason, sales employers may need to alter their business to suit these preferences. 

The good news is some of the flexibility that millennials often looked for in other careers, such as work-from-home options, is now widely used in sales.

Fortunately, natural-born sellers are still out there; you just may need to change your traditional recruiting approach to get in front of them.

Here are a few tips to help you attract millennials who possess an innate ability to sell:

• Know your audience and do your best to cater to their needs. For example, if you want to attract high-performing, tech-savvy millennials, you might consider offering a remote work program to entice them to work for you. Just make sure the adjustments you make to attract your ideal salespeople do not negatively affect your business in the long run.
  
• Offer an attractive salary and commission structure. Many salespeople are motivated by money. So to convince them to work for you over another business, you need to make sure they are able to reach their income goals. While this may cost your company more money upfront, it will pay for itself in the form of better salespeople and increased revenue for your business. Millennials with a high Need for Achievement will be attracted to a tiered commission structure and see it as an enticing challenge to reach each new commission level.
  
• Utilize your network. People are often much more likely to consider a job if it has been personally recommended by someone they know. So, reach out to your network (friends, family, and colleagues) to see if they know any talented salespeople who could be a good fit for your business.
  
• Position your sales job the right way. Inform candidates that you realize sales is about problem-solving and relationship-building rather than swindling people or using outdated, sleazy sales techniques. This will help them overcome any negative preconceived notions about working in sales for your company.

Keep in mind that you should not have to convince someone to want to sell at a high level – you should only need to convince them that working at your company as a salesperson is a smart career move.

Driven salespeople are competitive by nature and will want to work for the best company [and will want to become the best in their department]. Be sure to highlight why your company will help them achieve their own goals.

2. Stigmatized

All too often, the general public perceives salespeople as pushy, sleazy “used car sales” types who will say anything to land a sale.

Additionally, cold calling for new clients has become a social taboo. In many ways, the sales techniques and practices that worked in the past are no longer applicable, as they’ve become heavily stigmatized within Western society. 

So, it is easy to understand how the stigma could cause many people to avoid sales jobs – they do not want to be thought of in that light.

If you feel like this problem is hindering you from attracting top sales talent, you might consider re-naming your sales positions. Common alternatives to “salesperson” include “account manager,” “business development manager” or “consultant.” These titles may put people at ease more than “salesperson.”

You can also ease a concerned salesperson by emphasizing in the job ad that you are looking for a candidate that can genuinely connect with customers to solve their problems, rather than someone that can simply meet sales quotas.

A Driven salesperson will be naturally motivated to close as many sales as they can to satisfy their Need for Achievement, so you do not need to ask them to use pushy sales tactics that make both them and the potential customer uncomfortable.

3. The Great Mismatch

Another significant reason sales positions are challenging to hire for is that the market and the candidate pool are often mismatched. The reasons why a person might apply for a sales job vary, and as a result, not all candidates applying for sales positions have the right traits to become a talented salesperson. 

When you hire a new salesperson, you have to be choosy. You do not want just anyone who possesses sales experience – you want the best salespeople who are capable of producing amazing results that boost your company’s revenue and profitability.

Unfortunately, natural salespeople are rare, and sales managers are often fooled during job interviews by salespeople who are good at masquerading as someone capable of producing top sales results.

Do not let a candidate’s charm be the sole reason you offer them a position. If you are an experienced sales manager, you probably have learned the hard way that sometimes the interview is the best sales you will ever get out of the candidate.

You want to hire a candidate that is Driven by success and will continuously push their own limits to achieve new levels of success; not someone who is simply there to make enough money to pay the bills.

Incorporate an objective sales assessment into your hiring process to help you determine whether your candidate has the innate ability to sell long-term. 

Remember, the best sales associates are those who have a high Need for Achievement, are Competitive and can remain Optimistic in the face of rejection. 

And, if you are hiring a remote salesperson, a high Need for Achievement is non-negotiable because you need self-starters who will perform even when you are not watching them.

4. Ineffective Hiring Tactics

Why are there so many sales jobs available? The answer partially depends on the factors discussed above, but ineffective hiring tactics may also be to blame. 

Good sales jobs might never reach the attention of talented candidates if employers do not embrace modern hiring techniques. So, let’s dig into how employers can adapt to hiring in a post-pandemic world.

How to Adapt to Hiring Post-Pandemic

Sales positions were some of the hardest jobs to fill in 2021. The recent pandemic has changed the way that many people work. 

Consequently, adapting to the post-pandemic economic landscape is crucial to the hiring process. Fortunately, employers looking to hire for sales jobs can take advantage of several attractive solutions.

So, if you are looking to hire new sales associates, be sure you are:

• Writing attractive job ads
• Reviewing resumes for clues
• Applying a sales assessment
• Conducting behavioral interviews

Let’s take a moment to explore these options more deeply. That way, you can choose solutions that are compatible with your sales positions, company direction, and business budget.

Writing Attractive Job Ads

There are thousands (if not hundreds of thousands) of candidates wondering how to find sales jobs. But if you are not creating and posting attractive ads to catch their attention, you might never find these talented workers.

Be sure to write attractive job ads and post them on social media sites like LinkedIn, your favorite job sites like Indeed or CareerBuilder, and your company website to increase your candidate outreach. 

Here are a few tips for improving your sales job ads in a way that attracts Driven candidates:

• Speak directly to the candidate’s pain points. For example, you might open the job ad by saying “Are you tired of sales jobs that do not give you the freedom to work from home and the potential to reach your income goals?” Then, you could position your company as the solution to those problems. This is a great way to hook a candidate from the start of your job ad.
  
• Tell the truth. Avoid exaggerating about your company and the position. That way, you set the right expectations and avoid attracting candidates who are not going to be a good fit.
  
• Talk about your company culture. Do not be afraid to show some personality in your job ad – doing so will make your company stand out from the rest.
  
• Be specific about responsibilities and requirements. Let all candidates know exactly what the job role entails so they are well prepared for it. Use bold, high-intensity language to attract high-Drive salespeople.
  
• Do not set the bar unnecessarily high. While it is a good idea to come up with a set of requirements, make sure you are not weeding out talented candidates just because they do not possess knowledge of your product or industry. Those things can be taught, but natural sales skills cannot.
  
• Format the job ad. No one is going to read your ad if it looks like a giant wall of text, so use white space and bullet lists to break up the text and draw the candidate’s eyes to the most important points.
  
• Include a call to action. Simply tell the candidate how to apply for the position – you may be surprised at how many sales job ads are missing this step.

Also, make sure that your application process is easy and straightforward – the last thing you want is for a qualified sales candidate to give up on your application because it is too tedious or confusing.

Reviewing Resumes for Clues

A candidate’s resume can reveal a lot of information about their potential success in the sales industry. For example, potential employees who lack sales experience may be more challenging to train and prepare for a sales position.

However, candidates with an employment history at a similar-sized company are bound to adapt to their new sales environment more quickly and comfortably. Naturally, you can also choose to enforce a pre-employment assessment to weed out incompatible applicants. 

Below is our guidance for looking for hidden clues in your candidates’ resumes that indicate high performance. We say “hidden” because it is relatively easy to create an impressive resume. There is a whole cottage industry developed around doing just that.

But high sales performance can be spotted in some very subtle and not so subtle ways . . . the choice of words, turn of a phrase, choice of hobbies or activities. And most of all, work history, because psychologists tell us that the absolute best predictor of future performance is past performance.

Now, let’s discuss a few key areas of the resume to review for high performance indicators.

Work history can tell you a lot about a candidate. 

It is ok to see a candidate changing jobs frequently early on. This is often the time when someone is finding their sea legs, but as their career progresses, look for some signs that the candidate has exhibited enough grit to go through the inevitable challenges any job presents over time. Top producers tend to stay at it for a while to see if their passion and energy can carry the day, and because they are naturally optimistic, they don’t run at the first sign of trouble.

Personal activities can also be good indicators of high performance. 

If a candidate seems to gravitate toward less competitive activities, for example, that is fine; but during the interview you may want to ask questions to better understand their level of competitiveness. Meanwhile, another candidate may clearly love competitive sports and seem to push themselves ever higher in their personal activities. This is a nice indicator of a high Need for Achievement and high Competitiveness. Both traits research shows are shared by top-producing salespeople.

Working while in college or starting a small business are also good indicators.

The student juggling a full-time class schedule and a part time job or the kid with the local lawn mowing business often winds up as a Driven and successful adult, businessperson and salesperson.

Remember, it is your job to keep probing and searching deeper into the information presented to you during the hiring process to spot true potential. You have several additional steps in the process to separate out those that will truly be great salespeople for your team, but it is important to start out strong with a thorough resume review.

Applying a Sales Assessment

Now that you have spotted some high-potential clues during the resume review, an excellent next step is to further vet your sales candidates with a sales assessment. As mentioned above, the best traits of high-performance salespeople are Need for Achievement, Competitiveness and Optimism so utilizing an assessment that measures these core, non-teachable traits and other skills important to your sales role is key.

To learn how to choose the right sales assessment for your company, continue reading here.

Remember, a sales assessment is designed to weed out those candidates who do not have the core aptitude to sustain high performance and identify those who do. Incorporating a sales assessment into your hiring process will give you the confidence to know that you are now ready to interview only high-potential salespeople.

Conducting Behavioral Interviews

Now that you have narrowed your candidate pool down to only high-potential salespeople, you are ready to conduct behavioral interviews.

The behavioral interview is an opportunity for you to ask the candidate questions that can describe their past behaviors in a sales environment and gives you a chance to dig deeper into their skills and fit for your open position.

Below are a few of our favorite behavioral interview questions to ask when hiring salespeople. 

Q: How do you know when you have succeeded?

A: Look for a candidate who sets very high standards and holds themselves accountable for reaching their goals.

Q: When was the last time you were competitive?

A: Look for a candidate who describes competitive situations as enjoyable, motivating and common.

Q: When was the last time you were rejected? What did you do to recover?

A: Look for a candidate who is able to put situations into perspective and get going on another goal, remaining resilient even after a tough time.

For a behavioral interview planning form and more than 50 interview questions, check out our new, second edition of Never Hire a Bad Salesperson Again.

How to Retain Top Talent

Approximately 33% of U.S. workers considered making a career change in 2020 and 2021. As such, employers looking to retain sales associates may need to institute incentives to keep their most talented employees.

Some of the best ways to retain top talent within the sales industry include:

• Offering increased compensation
• Proposing a pay bonus scale based on sales numbers
• Keeping communication consistent, friendly, and helpful
• Asking employees about their professional needs and wants
• Providing free or discounted training and certification for talented employees

Choosing to embrace these incentives is a fantastic way to encourage your top talent to remain with your company. That said, asking your employees what they’d most like to see improved or changed may be one of the best ways to encourage employee retention.

After all, employees that feel respected and appreciated are less likely to pursue alternative positions or careers. So, if you are not sure where to start, poll your top talent to discover their most significant concerns and professional goals.

Why Sales is the Greatest Profession in the World

Are sales jobs good? Retailers and salespeople have existed for almost 6,000 years, since the rise of Mesopotamian civilizations like Sumer and Ur. As such, sales is one of the oldest trades/industries in the world. Considering this longevity, it is doubtful that the sales profession will ever disappear.

Whatever you do, avoid settling for an ineffective interview and hiring process simply because that is what your company has always used. If you are reading this article, chances are your sales hiring process is falling short and you are ready to start hiring long-term salespeople that are true producers.

By implementing these 4 simple sales hiring tips today, you can transform both the quantity and quality of your sales candidates and find those Driven salespeople who will jump-start your company’s growth, find new customers, and ultimately, increase revenue.

Sales may just be the greatest profession in the world. 

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