What to look for when hiring your first sales rep

What to look for when hiring your first sales rep

Far too many people think that the quickest way to create a profitable business is by introducing a sales rep onto the team early to begin closing deals and acquiring customers. Because of this, plenty of startups tend to create sales teams earlier than they should, which can become a costly mistake. 

Certain startups tend to have different issues, and they wait far too long to hire a sales rep for their team. Unfortunately, that could lead to missing out on opportunities, disorders, and revenue loss. Tons of people will usually advise you that you’ll know when it is the proper time to hire a sales representative. Of course, if that advice were true, then there would not be too many people searching for information on when they should recruit a salesperson onto their team.  

Most people are unaware of how to deal with this issue, and they’ll either hire a salesperson far too early or later than they should have. There are several ways you can determine when it is the correct time to onboard a salesperson onto your team. Opinions on this subject vary and will depend on the current stage of your company.  Take everything written here into consideration and assess what may work for you. Even if it doesn’t entirely point you in the right direction, you will at least be better prepared to make informed decisions about the best way to hire your first sales representative. 

What is your organization's current position?

Take a close look at your current team, and consider how well have sales been performing? Several organizational structures appear in startups searching to grow their sales team. 

The company’s first salesperson is the founder

One of the most typical situations for new startups is the salesperson being the business owner. The founder is aware of how the product works and can sell it to anyone better than anyone else. Not only are they in charge of selling the product to the customer, but the investors and new employees as well. Early-stage founders usually rely on themselves to prospect and chase after new business opportunities. It also places them in a position where they can sell people on their vision for the product, service, or brand. While this is a crucial step for most new businesses, it’s not feasible for long since the founder will start to take on more responsibilities as the business grows. 

Marketing managers

There’s a good chance that you have hired a marketing manager at this point in your company. Even new startup founders are aware that excellent marketing can have a good effect on their new business, which is why founders hire a marketer before a sales rep. Nevertheless, if you have been experiencing a successful marketing lead, your need for a sales rep who can close them will start to become increasingly visible. 

Aside from who is currently on your team, other critical factors you need to consider are your budget, along with your current and expected funding. When it comes to assessing your budget for your first sales hire, do not forget to consider these questions:

Don’t take too long to hire

If you have been spending time closing sales by yourself, the temptation to continue doing it increases. The idea of having to spend time and money searching for someone to hire to take your place sounds too troublesome. However, as a founder, you are going to have more responsibilities on your lap, such as running the organization. 

If you are currently unable to afford it, then yes, put it off for the time being. However, you need to ensure that the decision is based on facts and not just a gut feeling. Don’t become overburdened with sales calls or assessing leads for longer than is required of you. Your skills and talent lie elsewhere and fit better instead of making sales. 

What type of sales rep do you need?

At this point, you mustn’t overextend yourself and hire a Vice President of Sales. While you are expanding your business, unless your company’s revenue is around $1,000,000, you are going to need someone more affordable. Selling is something you are not quitting, but the person you hire needs to eventually be capable of managing a small sales team. 

Even if you struggled through the selling aspect of your business, you succeeded at making it this far and scaled your product that meets the market, so you must continue developing on that success. Hiring sales reps to assist you with boosting demand is where you need to concentrate your efforts. 

Hiring your first sales rep 

Getting the correct sales rep that fits your organization is of the utmost importance. At first, you may be tempted to save on your finances and go for someone with barely any sales experience but tons of determination. Never hire someone who barely has any skills in sales. The lack of skill and understanding could do far more harm than good to your brand. 

However, the first person that walks into your interview doesn’t need to be the most knowledgeable salesperson around. They merely need to have some years of experience and a decent understanding of what the sales process entails. Typically, you want someone who has at least three to five years of experience in sales. Although that may not be possible, make sure to stay away from the ones who barely have any understanding of sales, and you should be fine. 

Here are some things you should ask yourself for the hiring process: 

  1. What numbers are you attempting to achieve?
  2. What is the annual recurring revenue you want to reach?
  3. Is it possible to approach it with the current headcount?
  4. As the founder, where do you wish to spend your time?

When you are hiring your sales representative, make sure you have a goal in mind. What exactly are you trying to achieve by onboarding this new hire? What revenue goals are you setting with this sales rep?

Too many companies hire sales reps far earlier than they should. Doing so leads to them adding more people in an attempt to fix their organization's problems without taking the time to handle the root cause of the issue. Set clear goals and processes for your sales reps in motion before you decide to recruit more people. 

Before the recruiting process

Before you launch your recruiting attempts, you need to come up with a list of notes and assumptions based on what you’ve managed to learn during your time as a salesperson for your organization. To figure out what type of sales rep your company needs, you need to gain some experience in selling to your customers. After all, every company is unique, and your business may need a more specific set of skills. 

When you’ve managed to do that, start building a salesperson persona for your potential candidates based on what you have learned. The persona needs to have a combination of soft skills, sales competencies, and experience. The years the person has spent selling, the sales cycle length, average contract value, and so forth. Once you have managed to build a salesperson persona, you need to consider any additional criteria required to improve the chances of success in the role. 

Work discipline 

Becoming the first sales representative of a startup company can be challenging. The sales rep needs to reach their quota and expectations, but this is just the starting point. The sales rep needs to be improving your sales deck, providing customers with feedback to the business leaders, keeping track of data, A/B testing email campaigns, interviewing potential sales hires, and much more. 

The first hire isn’t merely taking on a simple sales role. They are someone you need that has the determination to work hard for your organization. Look for people who have been in a leadership position of some sort, it does not need to be work-related. If they were captain of a sports team or have a military background, to see if there were leaders in those fields. Digging into their past also provides you with crucial information, such as when they started working and if they have gone to college are solid indicators of their working discipline. The background you managed to dig up will provide you with insight on whether they are willing to make the commitment and disciplined employees. 


The foundation of coachability is humility. The salesperson needs to be coachable, and you can figure this out by noticing if they are eager to learn, thirsty for feedback, and humble. Coachable sales reps need to accept feedback and run with it to improve performance rates and the team's process. The best reps learn something new every day, and they are honest when it comes to requesting coaching. 

During the interview process with a potential candidate, listen to how they respond when you try to coach them into something. If they say they like doing things one way or are unagreeable with how you want things done, those can be indicators of a person who does not wish to learn from others. 

Former experience

Unless the person you are hiring is relatively new to the field, you must have the history behind the candidate's previous experience. Never hire your first sales rep without having concrete confirmation that they have some form of experience in this line of work. While it’s okay to take chances once your sales team starts to expand, you should never do this with your first hire. Your organization's survival needs to nail your first hire. Continue digging into their history until you are satisfied with the answers they gave you. 

Ask them questions that a salesperson should be capable of answering, such as the entire sales funnel and checking their answers to make sure they are correct. Here are several questions you can ask them:

If the numbers on their resume are not adding up, then you need to dig deeper. Point out the inconsistencies behind the math, and request them to walk you through their revenue numbers. If they can’t perform this task, then they are not someone you want on your team. 

Consider hiring two sales reps

Hiring your first sales representative can be exciting for any business owner since it's a great indicator of the business growth process. Not only does that mean that they can pass on the sales process to someone else, but it also means onboarding someone far more experienced than you at selling. Because you have managed to establish a process, they are going to surpass your sales numbers in ways you didn’t think were possible. 

However, while you might consider hiring only a single sales rep, it might be best to get yourself two of them. It may seem like a daunting task, especially when you have limited funds. Hiring two sales can provide you data points to measure success. Plus, hiring a salesperson is not as expensive as most people think. The sales rep will only receive their bonus if they are capable of closing revenue, which is an indicator of growth. 

Hiring two sales reps offers you some insights and improves the process. For example, let's say one of them succeeds while the other fails terribly. If you only employed a single rep, you wouldn’t be aware if it was because of your product, the individual, or because of another possible reason. Hiring two reps will offer you a better understanding of your sales process and bolster your confidence for future recruitments.  That allows you to formulate ways you can fix these issues.  


The first sales rep needs to be someone who can handle the sales process with confidence. If you hire someone with barely any experience in sales, the problem you are going to deal with in the future can be severe. Make sure to take everything in this article into consideration when you are recruiting your first sales rep.