When Should You Hire A Salesperson? What Founders Need to Know

Having a good salesperson or sales team can be the difference between life and death of your company. Salespeople generate revenue for a company — something essential for your business’s survival. So making sure you build the right team is critical. In this blog post, I’ll explain: when to hire, how to hire, how to measure sales, and when to expand. Below, you’ll find questions that you need to ask at each stage of hiring a salesperson and create a strong team to grow your startup. 

When to Hire

As a founder, you have revenue goals, but as your company grows those goals will grow and your allocated time for sales will increase. There comes a point where you can no longer keep up with sales. This is usually when you are spending over two hours a day on sales. Here are some questions to ask yourself:  

  1. What else in the startup needs your time and attention? 
  2. Are you spending over two hours a day on sales alone? 
  3. Do you understand the sales cycle?
  4. What are your revenue number goals and can  you reach those revenue goals alone?
  5. Who else on your team can help reach those goals?
  6. Would the salary and commission for hiring someone in a sales role be offset by potential revenue generation they would bring in? 


If reaching your sales goals is becoming a significant challenge, it’s probably time to get help or hire a salesperson. 

How to Hire

In the hiring process, a good place to start is hiring a Vice President of Sales, especially if you or our co-founder does not have a background in sales. They can help you determine and shape sales methodologies and processes. When hiring for this role, you’ll want to consider the following:

  1. What are their values, and are their values aligned with your organization’s? 
  2. What other motivations do they have to bring to the company?
  3. Do they possess the necessary sales skills your team will need? 
  4. Do they have a proven past sales record, and will they reach revenue goals? 
  5. Will they be coachable, and help coach the team in turn? 
  6. Have they worked for small organizations in the past?


Determining what you want out of your salesperson will help determine what questions you should ask in the interview. But if you’ve never hired for a role like this before, you might want some support. That’s where our upcoming course Hiring Your First Salesperson comes in.

How to Measure Sales

Founders must also set company goals and establish ways to measure the sales team's success. As part of your ongoing financial projections, you need to map out the sales cycle and determine realistic numbers based on actual sales possibilities per month. 

Essentially, you have to understand unit economics. Here’s an example: 

Imagine you are selling your product through ecommerce. It takes a customer three times to visit your site to get a sale, and it takes 1000 customers a month visiting the site to get one to convert to a sale. So if you want ten sales a month, then you need 10,000 people visiting your site, and you need them to return three times. Similarly, you will want to establish those metrics for your salesperson. Here are some questions to ask to make sure you’re setting the right goals: 


  1. What are the unit economics for the company to be profitable?
  2. Are the sales processes repeatable and scalable?
  3. Are the sales processes in line with the company’s unit economics?

How to Spot Red Flags

When you’re early on in a business’s lifecycle and funding is scarce, there’s nothing more worrisome than hiring the wrong person for your team, especially when it comes to sales. In our course, Hiring your First Salesperson , I cover some red flags to look out for. Questions you’ll want to ask when hiring that core member of your team include:  

  1. Does your candidate possess a lack of humility? 
  2. How can you tell if they lack consistency? 
  3. Is there a lack of focus on metrics and KPIs?


Finding a salesperson who is  consistent and collaborative, and who focuses on processes that are repeatable and scalable will lead your company to success. Establishing humility, consistency, and a focus on metrics early on will result in strong long-term team culture. 

When to Expand

When you’re a startup founder, you’re used to the pressure of wearing every hat in your business. So figuring out when the right time to expand can be challenging. You’ll want to avoid these common pitfalls, and our upcoming course will help you avoid those mistakes. In the meantime, you’ll want to ask yourself: 

  1. Why is your organization expanding? 
  2. How will this expansion advance your organization?
  3. How will this expansion solve organizational problems? 
  4. Can somebody on the team absorb this need already?
  5. Is there a tech, partnership, or alternative solution before hiring somebody? 
  6. What does the salesperson have to bring in to pay for his salary and beyond?

If the questions are exhausted, it sounds like it’s time to expand and I want to make sure you do it the right way! If you know your startup is in need of its first dedicated salesperson, the upcoming course in our Founders Sales Series is perfect for you. Join me for 4 weeks of learning and hands-on coaching that come with Hiring Your First Salesperson. Click the button below to learn more and register now!

Learn more and register!

Aaron Bare Aaron Bare
Aaron has been a lecturer/adjunct professor on Innovation and Entrepreneurship for 10+ years. He holds a Global MBA from Thunderbird School of Global Management. He currently lives in Tempe, Arizona.

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