How to Hire a Top Freelance Salesperson

By: Jack Reamer |
 December 11, 2023 |

I once worked for a company, where the founder had an insane amount of churn. 

Employees were leaving every month or so, despite free training and decent salaries. 

He had no idea why he kept hiring the wrong people for the job. 

And I don’t think he was alone in feeling this way. 

Hiring the right sales rep can be a challenging task. 

As you can see in the LinkedIn poll above, 100% of voters find hiring a new employee or sales rep a frustrating process. 

You don’t want to waste time and money on training a freelance sales rep, only to have them leave after the first month. 

Or perhaps, you have made a hire, and the sales professional is actually not a professional at all, but rather really bad at their job. 

If this sounds all too familiar, keep reading.

We decided to help readers by putting together a step-by-step process for hiring a top 1% freelance salesperson

NOTE: The tips outlined in this article can apply to other roles as well, not just a salesperson. So whether you’re looking to hire an account manager, copywriter, social media guru, or SEO boffin, you can use the framework and tips below. 

(P.S: Have you ever wondered if hiring a lead generation agency might be a better option than hiring a freelance sales representative? Read this article: In-House VS. Outsourced? And How to Build Your Own Lead Generation Team  OR Need help? Book a free 15-minute strategy session below with Salesbread.)


In this article, we will share how to find freelance sales agents on Upwork

The reason we have chosen Upwork is because there is a large pool of talent on the platform, and we have personally made successful hires using this platform.  

You don’t have to use Upwork, there are many other online job platforms that you can look at, but similar principles apply when it comes to hiring the right person for the job.

First consider: Which roles can you outsource? 

List Managers

One of the easiest roles to hire and hand off, but also one of the most important roles, is the List manager.

So everytime you start with a fresh list of prospects, each row needs to be cleaned up.

You need to check the prospects name, you need to fix the company name, (when you’re sending a cold email, you don’t send for example,

You need someone to help you clean up your data and fortunately this is a task that can be done at a low hourly rate. Essentially you need data entry for someone who speaks English, and once the list is clean, you can hand it off. 

But what about the harder hires?


So in our experience, the hardest role to hand off is the copywriter

The copywriter owns so much of the results when it comes to lead generation for cold email, or Linkedin outreach.

Before you hand the copywriting off, you have to be 100% sure that you’re working with someone who is a pro. 

Prospectors – List builders

When it comes to the prospecting inside of your sales team, should you just rely on list building tools? Or hire a VA to use the tools?

At our agency we use a couple of tools and scripts. Half of them are made in house, the other half are subscriptions to well done prospecting tools, like Crunchbase and Linkedin Sales Navigator. 

We even have a Yelp API, that helps us scrape data to find brick and mortar businesses for example. 

At Salesbread, we actually view list building as a role for a developer.

We may tell a developer on our team: “Hey can you please run a scraper that finds companies that match XYZ criteria.”

They will then go ahead and scrape directories, or Google.. Prospecting/list building is more of a technical role. 

This is outsourced to a developer or to someone who is a pro at web scraping. 

Once the developer has given you a list, you can then hand it off to the list manager to clean. 

Note: There are plenty of opportunities for outsourcing from the beginning of your sales process to the end. As a founder, think about what you would like to handle, and then outsource the rest to experts.  

Think about which hiring roles will free up more time for you

Write down all the tasks that you need to do in a day.

Let’s for example say that one task is email copywriting.

You could then hire an email copywriter, and hand this task over.

By doing this you free up your own time, to do other things in your company that you enjoy doing.


Here’s how to structure the process of hiring someone for outbound sales

You don’t want to spend hours and hours on hiring someone.

This should literally take you 5 minutes per day.

And hiring the right person is an essential stepping stone to freeing up more time for you as a founder.

By applying this process, you’re going to cut out a lot of applicants who are just a waste of time. These steps are a series of filters that will help you spend time on only the best applicants. 

Step 1: Write a job spec with “secret questions.”

A job spec can vary. It doesn’t have to be a long 3 page explanation of what the role entails. It could simply be 10 bullet points of the job description.

Add a challenge into the description

It’s important to note that most people don’t actually read the job spec. 

An option is to include a challenge in the job spec. Perhaps before they even apply, they have to first answer some questions. If they never read the job spec, they will fail at the challenge. 

If a person isn’t methodical, they won’t see the challenge, and then they will fail. You want to sprinkle in the challenge subtly.

Remember your time is precious, and you don’t want to waste it on candidates that don’t read your post thoroughly.

Here’s an example:

“Ability to follow instructions and write “Koloa” when being asked about your favorite animal.”

This is a screening question, but you can ask pretty much anything; It;s just a test to make sure that they actually take the time to read through everything.

So this will probably be your applicants first test, as to whether or not the person will be a good hire. 

If the person applying actually took the time to read your job spec, that’s a good start. 

People should read the job spec, because it highlights what they need to know about the job, and they should be happy to actually do the work that’s outlined in the description. 

This step filters out people who might not be a good fit for the role. 

Another option is to ask the candidate why they would like to work for your company.

You want someone who really wants to work for you, and not just someone who is applying to a job for the sake of applying.

You could even ask them to add in their cover letter the answer to what’s 6+3. 

If you see the answer 9, it’s a visual clue to you that they read the job spec. 

This visual clue will help you weed out candidates who can’t follow instructions. 

So if you see the word Koala and the character 9, you can spend more time on the application. For applicants who never included these answers, you can just reject the application.

Option 2 – Filter and use web scraping

You could also scrape Upwork by using specific keywords of things that are important to you:

You might be interested in their:

  • Years of experience
  • Proven track record (This could be their ratings on upwork.) 
  • Do they have experience with certain CRM tools, or microsoft and excel
  • Are they specifically trained for B2B sales?

You could filter a list, and then look for these specific key terms. You might have a list of 20 candidates and then narrow it down to 10, depending on their bios and what works for you. 

Once you have your top 5, you can hop on an interview with them, hire 2 for a trial period and see which candidate performs the best.

Be specific about what you expect from the candidate

Remember it’s important to outline exactly what it would be like to work with you. 

For example, mention if the position is commission only, or if they need to work well under pressure.

It’s also important to mention the time zone that the person will need to be working, as well as the number of hours you expect them to work. 


Because some people are looking for part time work, others are looking for full time. Others might be looking for long term contracts.

You want to minimize the amount of questions people might want to ask outside of the job description. If you’re specific about what you need and expect, it will save you time, and attract the right candidates. 

Step 2: Make sure the sales consultant is worth the interview

There are a few short tests that you can do to see if the sales rep/candidate is worth the interview. If they complete these tests well, then they might be worth an interview.

This will ensure that you don’t waste time. 

An assignment test specific to the role you are hiring

You could ask the candidate one specific question, and see how well they answer the question. 

For example you could simply say: 

“Thanks for applying, here is a test to complete before going on to the next step.”

You could ask them to complete a free speed typing test and send you the results. Or complete a test through MTD, which is a free sales assessment test.

Or for salespeople, they might complete a writing sample, send a video of them role-playing a sales call, or conduct customer research.

If you would like a copywriter specifically for cold email or LinkedIn outreach, give them a screenshot of a LinkedIn page, and ask them to find 5 points worth talking about for personalization. 

If they get less than 5 points, they will automatically be disqualified. 

They can then paste their results in the message chat.

If they pass, they can do an interview, if not you could just say that they didn’t meet the requirements. 

Step 3: Send your calendar link to the candidate and ask them to complete a psychological test

By asking someone to complete a psychological test, it allows you to see what kind of person they are. You could ask the sales executive to complete the  Meyer Briggs 16 personalities test. 

This test can give you insights into the candidate’s personality and see whether or not they would be suited for a sales representative job

They need:

  • Good communication skills
  • A competitive spirit 
  • Confident
  • Determined under pressure
  • A sales rep needs grit and not easily give up after being rejected countless times
  • They also need to be adaptable and assess client needs. This will help them pivot their pitch. 

As an interview, these insights will help you know their strengths and weaknesses and you can interview them according to this. This test is just a gauge but if the candidate is really interested in working for you, they will just through hoops to get to the final stage. 

And this is what you want to assess. If they want your time, they need to be willing to use their time to apply. 

Step 4: Have the interview and make sure they share your values

If you’re planning on building a company, you want to have employees that share your values. 

This is especially true if you are hiring people for marketing strategy positions, a CMO, or sales VP. 

For those who are in control of lower tasks, they can receive an SOP and follow it to the tee. 

But if you want your company to grow and thrive, you need to hire someone who shares your values and sales goals; especially if you would like to hand off important tasks to your employees. 

Interview Questions

When it comes to interviewing questions, rather ask them to give you examples (behavioural questions.) 

You could say: “How would you respond if potential clients said X?”

This will help you dig to see if they demonstrate some of the core values that you have.

Here are some more interview question examples: 

Pro tip: Ask the candidate what they expect from you as the employer

These answers might shock you, but it also helps weed out candidates who might be a bad fit for your business. 

But this question also helps you be a good employer to those on your team. You want to do your part to make sure that your employees have a happy work environment.

You want your employees to have fun and success because this will ensure that they stick around. It’s not easy to find good people.

Communicate with your new people when they are great and reward them for their hard work. 

There you have it…

If you’re looking to hire a top 1 % salesperson, use the tips above. This framework has helped us at Salebread to find really good hires…  

Just remember to also do your part as an employer. This will ensure that you have low churn at your company and that these good employees stay with you for many years to come.