Back

The Truth About Hiring A Sales Rep (A Guide To Know How And When)

December 11, 2020
by
Kyle Vamvouris
The Truth About Hiring A Sales Rep

Hiring a sales rep is no easy task, especially when you are growing a startup. 

To make matters worse there is a lot of conflicting advice out there on when is the best time to start hiring a sales rep. 

But don’t worry, I made this post to guide you through your hiring journey to help ensure that you add the absolute best candidate to your team. 

Know What Kind Of Sales Rep You Are Looking For

The first thing to understand is that sales reps are not one size fits all. Every company has different challenges and upsides. 

Especially in the remote world we live in today, a sales rep from ‘Corporate America’ with a great track record could be the wrong fit or a perfect fit. 

There is one trait that is common across all high performing sales reps. High work ethic. This is a trait that all of your employees should have. But it is even more important in your sales team. 

To break up the types of companies into two groups, we have:

  • Early-stage companies without a vetted sales process
  • Established companies with a vetted sales process 

These two company types need different sales reps. 

Early-stage companies need a more dynamic generalist who can help create the sales process and will be good at whatever you throw at him/her.

Your first few sales department hires are critical, because they will lay down the groundwork for the rest of the team. Not to mention, if you’re an early-stage company, you need more revenue and you need it now. 

As companies grow and mature, they create a sales process based on the results and experiences that have happened thus far. After plenty of time spent testing and tweaking the sales process, a company will only need someone with a high work ethic and experience. 

When a company has a vetted sales process, it is ok to hire someone who is not a dynamic generalist. The primary advantage of a non-dynamic generalist is they are more common and less competitive to hire. 

Someone with a high work ethic who is trainable will soon perform at the standard of the company. This can happen because the groundwork has already been completed, and the new sales rep just needs to follow rules, not create them. 

When Is The Right Time To Hire Your First Sales Rep?

The timing is always tricky, and the fact of the matter is that knowing the correct timing to hire your first sales rep is an opinion. 

But what most of the experienced salespeople can agree on are the bad times to hire your first sales rep. 

In reality, there are only two potential bad options, you can:

  • Hire too soon
  • Hire too late

At first, it is very important that one of the founders is the salesperson in the organization. There are simply too many lessons to be learned from being in direct contact with your customers.

This will help you validate that there are customers who are actually interested in your product/service. As time goes on, being the first salesperson will help you refine your target market, and give you insights on what their pain points truly are. 

In other words, being the first salesperson allows you to listen to the objections of the customers, and figure out how to deal with them. 

This will help you craft your offerings into a more desirable solution for the customers. As an entrepreneur, being in the trenches, chasing down leads, and tweaking your offering to match the needs of your target audience is a great way to create a successful business. 

Once again, knowing when to hire your first sales rep is more an opinion than anything else, but to give you some guidelines to follow,

You should seriously consider hiring your first sales rep when:

  • You close at least 10 deals, each with at least a LTV of $5k
  • You have been handling all of the sales yourself successfully for 90-180 days
  • You have a clear sales process that is working

But here’s the thing, if you are able to close the larger accounts consistently by yourself, your resources may be better spent on hiring an SDR. This way you can have the SDR do all of the prospecting and set up meetings for you, then you come in and close the leads. Not to mention, SDR’s are more affordable than sales reps. 

One common problem startups face when hiring the first sales rep is that there are no previous sales standards set. This can happen when a founder has little sales experience or has not closed many deals in the business yet.

And since there are no sales standards set in the company, it can be difficult to tell if a sales rep is performing well or badly. 

To compensate for this, hiring two sales reps at the same time will allow you to better understand what the standard for a high-performing sales rep is vs a bad one. This consumes a lot of resources, and I only recommend this to startups with founders who have little sales experience. 

A common question that companies ask me is:

"Should we hire a group of sales reps, or one at a time?"

This depends heavily on the scale of your business. 

If your business is large, then you can easily hire a group of reps and onboard all of them at the same time. 

But if your business is in the start-up phase, then you won’t have the resources to hire that many people at once. Also hiring a bad sales rep would have a serious impact on your business during the startup phase. 

What this all means: If you have a vetted sales process and enough resources to hire a group of sales reps, then I recommend it. But if you are a startup without a vetting sales process, then hiring one rep at a time is the best solution. 

Make Sure The Sales Rep Has A Track Record Of Success

A proven track record of success means the person has a high chance of generating revenue. 

This is important because you don’t want to waste your time with people who cannot perform. If you are hiring some of your businesses first sales reps, this is even more important! 

Unfortunately, not everyone is telling the truth on their resume. Some of your candidates high performing sales numbers might be a little bit fudged, or an outrageous lie. 

85% of job applicants lie on their resumes…… Yikes!

If that doesn’t demonstrate the importance of validating a candidate’s track record, then I don’t know what will!

A few of my favorite ways to validate anyone’s track record is to reach out to their former co-workers and find other people who can verify the numbers for you. And while you’re at it, ask about what they thought of the candidate you are considering to hire. 

Another good way to validate their track record is to ask about the specific numbers that lead up to the total sales they claim they made. 

If a candidate tells you about how many cold calls they were making per day to get to $X in sales per quarter, ask them questions about how many prospects they looked at in a day, their deal sizes, and closing rate. Start to calculate the math to figure out if all the numbers in the steps add up to what they claim their sales to be.

Chances are if they are lying about their performance numbers, they will not be prepared with all of the numbers around how they actually got to the total sales. Look to see if they are nervous about answering these detailed questions. 

Not only will this help you to understand if they are telling the truth, but it also gives you insight into how thorough they are with their work. 

Look For Someone Who Believes They Are Capable Of Great Things But Acknowledges That They Haven't Done It Yet.

Mindset is everything in sales. Having confidence and believing that your companies offerings are valuable is the first step in convincing the customer that you can solve their pain points. 

The best trait to look for when hiring a sales rep is the “make it happen” attitude. Ask them about past experiences and examples that demonstrate how hungry they are. This “make it happen” attitude is the heartbeat of a high performing salesperson.

Candidates cannot be taught this type of hunger, and must create this desire on their own -- hence why it’s a great trait to look for. 

Get To Know Them As A Person


A great way to make sure you get the best candidate when hiring a sales rep is to ask the best sales interview questions

But to give you an overview of these questions, you’ll want to focus on learning the candidate’s experience, and who they are as a person. The exact answer they give is not what’s most important here, It is how the candidate answers your question. 

Some of the best ways that I find to truly get to know someone is to take them out to dinner, and to casually ask them personal questions.

A restaurant setting and aroma is perfect to get people to relax and show you who they really are. Treat them like you would one of your friends.

Plus, who doesn’t like a good meal?

Be Quick To Fire

No one enjoys firing an employee. Not me, not you, not even the devil himself! (well ok he might enjoy it)

So think about it this way, if you keep a poor performing employee in your organization, then other members of your team will start to follow suit. Soon after that, the company culture has shifted in a negative way. 

One thing leads to another, and it is time for a round of layoffs that impact the lives of a lot more than one poor-performing sales rep. 

But all of this could have been avoided if the single bad employee was cut. 

Odds are if you are hiring some of your first sales reps your company is small and you know everyone on a personal basis. The good news is that this means it is a lot harder to hide in the company, and more people are accountable for the actions that they take. 

With a smaller company, it is easier to track the direct effect of an employee and to know their performance numbers. 

The bottom line is that if you can determine an employee is not the right fit, then you have to cut them loose. The earlier you can determine this the better.

I wish you the best of luck with filling your sales rep position! 

I remember my first time hiring a sales rep, and how difficult it was to finally select one of the candidates. I hope this post helped you make your decision.

But if you’re still stuck and need some help, check out what we do.

I look forward to hearing from you!

Similar Posts

How to write and use Email Templates for Sales Success
Continue Reading
Sound More Confident on Cold Calls by Improving Your Vocal Tone
Continue Reading
9 Follow Up Email Templates
Continue Reading
GuidesSalesTechnology
What We Do
March 13, 2021

The Truth About Hiring A Sales Rep (A Guide To Know How And When)

Kyle Vamvouris

Hiring a sales rep is no easy task, especially when you are growing a startup. 

To make matters worse there is a lot of conflicting advice out there on when is the best time to start hiring a sales rep. 

But don’t worry, I made this post to guide you through your hiring journey to help ensure that you add the absolute best candidate to your team. 

Know What Kind Of Sales Rep You Are Looking For

The first thing to understand is that sales reps are not one size fits all. Every company has different challenges and upsides. 

Especially in the remote world we live in today, a sales rep from ‘Corporate America’ with a great track record could be the wrong fit or a perfect fit. 

There is one trait that is common across all high performing sales reps. High work ethic. This is a trait that all of your employees should have. But it is even more important in your sales team. 

To break up the types of companies into two groups, we have:

  • Early-stage companies without a vetted sales process
  • Established companies with a vetted sales process 

These two company types need different sales reps. 

Early-stage companies need a more dynamic generalist who can help create the sales process and will be good at whatever you throw at him/her.

Your first few sales department hires are critical, because they will lay down the groundwork for the rest of the team. Not to mention, if you’re an early-stage company, you need more revenue and you need it now. 

As companies grow and mature, they create a sales process based on the results and experiences that have happened thus far. After plenty of time spent testing and tweaking the sales process, a company will only need someone with a high work ethic and experience. 

When a company has a vetted sales process, it is ok to hire someone who is not a dynamic generalist. The primary advantage of a non-dynamic generalist is they are more common and less competitive to hire. 

Someone with a high work ethic who is trainable will soon perform at the standard of the company. This can happen because the groundwork has already been completed, and the new sales rep just needs to follow rules, not create them. 

When Is The Right Time To Hire Your First Sales Rep?

The timing is always tricky, and the fact of the matter is that knowing the correct timing to hire your first sales rep is an opinion. 

But what most of the experienced salespeople can agree on are the bad times to hire your first sales rep. 

In reality, there are only two potential bad options, you can:

  • Hire too soon
  • Hire too late

At first, it is very important that one of the founders is the salesperson in the organization. There are simply too many lessons to be learned from being in direct contact with your customers.

This will help you validate that there are customers who are actually interested in your product/service. As time goes on, being the first salesperson will help you refine your target market, and give you insights on what their pain points truly are. 

In other words, being the first salesperson allows you to listen to the objections of the customers, and figure out how to deal with them. 

This will help you craft your offerings into a more desirable solution for the customers. As an entrepreneur, being in the trenches, chasing down leads, and tweaking your offering to match the needs of your target audience is a great way to create a successful business. 

Once again, knowing when to hire your first sales rep is more an opinion than anything else, but to give you some guidelines to follow,

You should seriously consider hiring your first sales rep when:

  • You close at least 10 deals, each with at least a LTV of $5k
  • You have been handling all of the sales yourself successfully for 90-180 days
  • You have a clear sales process that is working

But here’s the thing, if you are able to close the larger accounts consistently by yourself, your resources may be better spent on hiring an SDR. This way you can have the SDR do all of the prospecting and set up meetings for you, then you come in and close the leads. Not to mention, SDR’s are more affordable than sales reps. 

One common problem startups face when hiring the first sales rep is that there are no previous sales standards set. This can happen when a founder has little sales experience or has not closed many deals in the business yet.

And since there are no sales standards set in the company, it can be difficult to tell if a sales rep is performing well or badly. 

To compensate for this, hiring two sales reps at the same time will allow you to better understand what the standard for a high-performing sales rep is vs a bad one. This consumes a lot of resources, and I only recommend this to startups with founders who have little sales experience. 

A common question that companies ask me is:

"Should we hire a group of sales reps, or one at a time?"

This depends heavily on the scale of your business. 

If your business is large, then you can easily hire a group of reps and onboard all of them at the same time. 

But if your business is in the start-up phase, then you won’t have the resources to hire that many people at once. Also hiring a bad sales rep would have a serious impact on your business during the startup phase. 

What this all means: If you have a vetted sales process and enough resources to hire a group of sales reps, then I recommend it. But if you are a startup without a vetting sales process, then hiring one rep at a time is the best solution. 

Make Sure The Sales Rep Has A Track Record Of Success

A proven track record of success means the person has a high chance of generating revenue. 

This is important because you don’t want to waste your time with people who cannot perform. If you are hiring some of your businesses first sales reps, this is even more important! 

Unfortunately, not everyone is telling the truth on their resume. Some of your candidates high performing sales numbers might be a little bit fudged, or an outrageous lie. 

85% of job applicants lie on their resumes…… Yikes!

If that doesn’t demonstrate the importance of validating a candidate’s track record, then I don’t know what will!

A few of my favorite ways to validate anyone’s track record is to reach out to their former co-workers and find other people who can verify the numbers for you. And while you’re at it, ask about what they thought of the candidate you are considering to hire. 

Another good way to validate their track record is to ask about the specific numbers that lead up to the total sales they claim they made. 

If a candidate tells you about how many cold calls they were making per day to get to $X in sales per quarter, ask them questions about how many prospects they looked at in a day, their deal sizes, and closing rate. Start to calculate the math to figure out if all the numbers in the steps add up to what they claim their sales to be.

Chances are if they are lying about their performance numbers, they will not be prepared with all of the numbers around how they actually got to the total sales. Look to see if they are nervous about answering these detailed questions. 

Not only will this help you to understand if they are telling the truth, but it also gives you insight into how thorough they are with their work. 

Look For Someone Who Believes They Are Capable Of Great Things But Acknowledges That They Haven't Done It Yet.

Mindset is everything in sales. Having confidence and believing that your companies offerings are valuable is the first step in convincing the customer that you can solve their pain points. 

The best trait to look for when hiring a sales rep is the “make it happen” attitude. Ask them about past experiences and examples that demonstrate how hungry they are. This “make it happen” attitude is the heartbeat of a high performing salesperson.

Candidates cannot be taught this type of hunger, and must create this desire on their own -- hence why it’s a great trait to look for. 

Get To Know Them As A Person


A great way to make sure you get the best candidate when hiring a sales rep is to ask the best sales interview questions

But to give you an overview of these questions, you’ll want to focus on learning the candidate’s experience, and who they are as a person. The exact answer they give is not what’s most important here, It is how the candidate answers your question. 

Some of the best ways that I find to truly get to know someone is to take them out to dinner, and to casually ask them personal questions.

A restaurant setting and aroma is perfect to get people to relax and show you who they really are. Treat them like you would one of your friends.

Plus, who doesn’t like a good meal?

Be Quick To Fire

No one enjoys firing an employee. Not me, not you, not even the devil himself! (well ok he might enjoy it)

So think about it this way, if you keep a poor performing employee in your organization, then other members of your team will start to follow suit. Soon after that, the company culture has shifted in a negative way. 

One thing leads to another, and it is time for a round of layoffs that impact the lives of a lot more than one poor-performing sales rep. 

But all of this could have been avoided if the single bad employee was cut. 

Odds are if you are hiring some of your first sales reps your company is small and you know everyone on a personal basis. The good news is that this means it is a lot harder to hide in the company, and more people are accountable for the actions that they take. 

With a smaller company, it is easier to track the direct effect of an employee and to know their performance numbers. 

The bottom line is that if you can determine an employee is not the right fit, then you have to cut them loose. The earlier you can determine this the better.

I wish you the best of luck with filling your sales rep position! 

I remember my first time hiring a sales rep, and how difficult it was to finally select one of the candidates. I hope this post helped you make your decision.

But if you’re still stuck and need some help, check out what we do.

I look forward to hearing from you!