How to Find (and Hire) the Right Salesperson

Finding the right salesperson is like catching a butterfly.

But the butterfly can talk.

And it probably has work experience and people skills.

And it should know how to dress well.

And it has good body language.

And it would freak a lot of people out if it could fly.

Well, I got a lot less mileage out of the butterfly analogy than I thought I would, but there’s one key similarity between finding a butterfly and a great salesperson. Both can be really hard.

Hiring an exceptional salesperson is a tricky process. There’s no universal blueprint that lays out every step to do it successfully. It takes a lot of finesse and good judgment — with some pure luck peppered in every now and then. That being said, there are certainly some steps you can take to set yourself in the right direction.

In this article, I’ll outline what you should do to put yourself in the best position to find and hire a great salesperson.

How to Hire a Salesperson

1. Set terms for your ideal candidate
2. Write a great job ad
3. Pick the right candidates for interviews
4. Pay special attention to candidates who reach out before the interviews
5. Ask thoughtful questions during your interviews
6. Make sure they ask thoughtful questions as well
7. Be thorough and transparent when describing what you need
8. Follow up with promising candidates quickly

1. Set terms for your ideal candidate.

When you’re hiring salespeople, you’re going to wade through a lot of applicants. And I’m not using the term “a lot” lightly.

According to the Jobvite 2019 Recruiting Benchmark Report, individual job requisitions in financial services received an average of 32 applicants each, while listings in information technology received 39.

And those figures may be considerably lower than what you could expect from your business. Run a quick search for “entry-level sales positions” in your area on LinkedIn. There’s a good chance you’ll find several listings with well over 100 applicants.

My point is, when hiring salespeople, you may have to wade through an ocean of resumes, so it’s important to know what you’re looking for.

Set terms for both your minimum and preferred qualifications for the position you’re trying to fill. Identify the relevant experience, education, and qualifications you’d like out of your ideal applicant. Use those to filter your applicant pool and only engage with prospective employees who are qualified to fulfill the responsibilities of the position.

2. Write a great job ad.

Once you’ve locked down what you want out of your ideal candidate, write a job listing that will resonate with that persona. If you want your job ad to register with the candidates you’re after, there are some things you have to be mindful of.

You need to optimize your job title to suit your target candidates. Try to hit keywords that they may be searching for, like “B2B” or “Entry-Level.” Don’t get carried away, though; you still want your title to be straightforward and convey the nature of the position.

After that, you need to write a company summary with engaging copy. Avoid just copying and pasting some boilerplate overview from your company website. Also, give some insight into what your specific sales team does day-to-day. Describe the company’s perks and benefits package as well.

And set clear, realistic job requirements — enough to register with legitimately qualified candidates without scaring too many off.

Finally, use strong verbs to describe the job’s responsibilities. Using creative yet authoritative language — think “enabling success” as opposed to “overseeing projects” — can excite potential candidates and help motivate them to send an application your way.

3. Pick the right candidates for interviews.

Take notice of the most personal applications you receive. If you’ve asked for a cover letter, take the time to make sure it’s not just some generic document that an applicant has been blanket-sending to every post they see on LinkedIn.

You want candidates that want you back. A personal, compelling cover letter can tell you a lot about how much this opportunity means to an applicant. If they put in the time to write a thoughtful cover letter and tailor their resume to suit your job description, they probably took the chance to work for you seriously.

Once you’ve identified the best applicants, start running phone screens. Call your candidates and see if their previous experience is legitimate, if they took the time to learn about your company, and how quickly they can think when put on the spot.

After using your phone screens to narrow down your applicant pool, you may want to conduct remote interviews. These should be slightly more intensive phone screens, and generally, you’ll use them to identify the applicants you feel are best fit for in-person interviews.

4. Pay special attention to candidates who reach out before the interview.

Touching base with an interviewer before speaking with them in-person is usually a sign that a candidate is putting extensive effort into preparing for their interview. It’s also a great way for them to demonstrate the confidence and thoroughness they can bring to the table.

Reaching out to an interviewer before an interview is inherently imposing. Candidates are often put off by the prospect of coming off too pushy or saying the wrong thing. And, honestly, that could very well happen. There’s a real possibility that their effort to reach out could come off as hollow or unproductive.

But, if they ask the right questions — like if there are specific materials you’d like them to prepare, what the name of everyone their meeting with is, or what the appropriate dress code is — they’re showing that they’re diligent and self-assured enough to do their homework and power through uncomfortable situations.

5. Ask thoughtful questions during your interviews.

You need to get a feel for who these candidates are beyond their resumes. When conducting an interview, you don’t want to just mull through technical questions without challenging candidates to demonstrate how they think outside of a conventionally professional context.

That process can mean asking good interview questions like, “Tell me about a time you screwed up,” or, “If I were to poll everyone you've worked with, what percentage would not be a fan of yours?”

You want them to reflect on things that they can’t necessarily brag about. That will give you a feel for how they’ll function as both an individual employee and a part of your team. Remember, hiring a salesperson with excellent qualifications who won’t fit your company culture or team dynamic may be more trouble than it’s worth.

6. Make sure they ask thoughtful questions as well.

Asking thoughtful questions is a great way for an applicant to demonstrate critical thinking skills and a genuine interest in your company. By asking great questions, a candidate is demonstrating a willingness to try and understand your business. They’re also showing that they know how to ask for help when they get stuck.

A candidate that asks specific, meaningful questions that extend beyond facts anyone can find on your website often ends up being a sharp, dedicated salesperson.

7. Be thorough and transparent when describing what you need.

Let your candidate know exactly what they can expect from this role. You want them to understand what they’re getting into — for both their sake and yours. If you hire someone who doesn’t have a great grasp on what they’re getting into, there’s a chance they may only stick around for a few months.

Tell them about what the role entails. Tell them about what could be hard about it. Tell them about some pitfalls they might hit, and gauge their response. You don’t have to be ominous and imposing about it; you just have to be honest.

Unless you’re hiring someone for a contract position, you’re looking for a salesperson who’s in it for the long haul. You can’t know if a candidate is cut out for a position if they don’t know what that position really is.

8. Follow up with promising candidates quickly.

If a candidate nailed an interview, let them know right away. Reach out and keep them engaged and interested in your company and the role itself. Let them know that they impressed you and give some information on next steps.

A great sales candidate can be a hot commodity. If a candidate you’re interested in is interviewing for multiple positions at other companies, you want to stay on their mind as much as possible. Getting in touch and scheduling next steps is a great way to do that.

Once you’ve arranged next steps — which often means more interviews — keep repeating most of the process outlined above. You might want to bring in additional interviewers, arrange scenario-based interviews, have candidates give presentations, or make them do anything else to demonstrate their practical understanding of sales.

Like I said, there’s no definitive step-by-step outline of the sales hiring process, but following the steps above should set you on the right course.

How to Find a Great Salesperson

We looked to the president of The Virtual CROCasey Murray for a few tips on what to do when you do find that perfect salesperson and added a few of our own.

Here’s how to determine if a candidate is a good match:

1. Encourage thoughtful follow up questions.
2. See how the candidates respond to your lead generation strategy.
3. Look for curiosity about new information.
4. Connect with candidates before the interviews.
5. Pay attention to detailed remarks about the company.
6. Invite cross-functional teammates into the interview process.
7. Watch for body language cues.
8. Play conversational tennis.
9. Be open to new ideas.
10. Listen for non-work accomplishments.
11. Negotiate more than money.
12. Prepare to answer uncomfortable questions.

1. Connect with candidates before the interviews.

A candidate reaching out to an interviewer before the scheduled interview shows a high level of confidence. If they ask whether there’s anything specific they should prepare — and go even further by presenting a few topics they hope to discuss — they’re definitely above average.

Set aside a half hour per week to respond to candidate questions via email and LinkedIn. Time is valuable, so keep it brief, warm, and on topic. A little extra effort goes a long way to show candidates that you care and are excited to meet them during the interview. Even if you don’t select the candidates, they’ll exit the process with a good feeling about your company’s brand based on your thoughtful action.

2. Encourage thoughtful follow up questions.

The quality of a salesperson’s questions during the interviews is a clear indicator of their ability to succeed. A good question goes beyond facts the candidate could have easily learned by looking at your company website or LinkedIn page. It delves into what’s needed to do well in this role.

As the interviewer, you can keep the good questions coming by encouraging the candidate to ask more of them during the interview. Share information about significant topics such as your compensation structure, growth opportunities, or quotas. These hot-button points should pique the interest of a great salesperson and encourage them to seek more specific insight into those areas of the role.

Here are some examples of thoughtful follow up questions a great salesperson might ask:

• What is the revenue for this territory for the last three years? Why did the last person leave this territory?
• Who is the number one competitor that you lose to, and what is being done to address any gaps?
• How long is the average sales cycle? What is the current renewal rate? How many customers have multi-year contracts?
• Do you pay salespeople commission on support renewals?
• What is the sales manager’s style?
• What is the most money a salesperson has earned on your team?
• What is your average close rate? What is the average follow-on revenue for install accounts?
• When you lose a deal, why do you lose?
• What is the barrier to entry for another company to offer a similar solution to yours?
• What mechanisms are in place to protect the Intellectual property of this company (patents, trademarks, etc.)?
• What did the highest-paid rep earn last year? How much did their quota increase this year?

Prepare specific answers to these questions ahead of time. Not only does preparation show the candidate that your company values these topics enough to keep track of the data, they give the candidate plenty of information to make a decision about whether the role will be a good fit for them.

3. See how the candidates respond to your lead generation strategy.

Salespeople have one main goal – to close business. In order to do that, they need a pipeline of leads. Whether your team is responsible for prospecting their own leads or your marketing team does the heavy lifting for them, a good salesperson should respond with questions about your lead generation strategy.

Good candidates might ask questions like “What is the average close rate on those leads?” or “Where do your sales reps have the most success prospecting? Online, in person, at events?” And an even more advanced candidate may ask about marketing vs. sales qualified leads and what activities work best to bring in more warm and qualified leads. These questions show that your sales candidate can think critically about business processes to help reach their goals.

4. Gauge their curiosity.

It’s a positive sign if the candidate asks a question that relates to any information they just learned. This shows they’ll be engaged and curious during meetings with prospects. An example would be: “You mentioned that the company recently hired a bunch of support engineers. Has there been an uptick in support tickets?”

As the interviewer, you may not think twice about mentioning the new hires in the engineering department. You’ve likely been briefed on why there was a need for growth at a company meeting. However, a curious candidate for a sales position might want to know why that team grew. An increase in support tickets could indicate an obstacle to overcome during the sale while new product features the engineers might build mean new offerings to share with a potential customer.

5. Pay attention to detailed remarks about the company.

A good candidate has done more than just look at your LinkedIn profile. They have done things like:

• Researched people at the company in the position they’re applying for
• Read online reviews of the company on Glassdoor
• Looked up reviews from Gartner or Forrester to see where your solution rates

Exceptional candidates will also research aspects of the business like its financial health, any debt it may have, and any planned discussion of future fundraising or IPOs.

Pay attention to questions like these. They signal that the candidate has a long-term interest in the company’s success, not just their own achievements.

6. Invite cross-functional teammates into the interview process.

Good candidates treat HR and administrative staff as a vital part of the interview experience. They recognize that how well they approach the processes of setting up meetings, exchanging emails, returning phone calls, sharing documents, and coordinating onsite visits demonstrates the kind of employee and coworker they may be down the line.

While HR and admin staff are usually required in the interview process, consider adding marketing or customer service team members to the interviews, too. Great salespeople know how to cultivate positive working relationships with both groups. This type of interview will show you which candidate can become a champion of your customer’s experience across all three functions.

7. Watch for body language cues.

Body language drives a lot of our non-verbal communication. While interviews can be tense for any candidate, a poised disposition is imperative in a great salesperson. Meeting new clients, especially those from high-profile accounts, requires a salesperson with a demeanor that is calm and welcoming.

Look for candidates who appear confident, maintain an upright posture, and make eye contact. Other nonverbal cues that are just as important as body language include tone of voice, facial expressions, and gestures.

8. Play conversational tennis.

Good interviewees understand the cadence of the conversation and know when to cut answers short and when to re-engage the interviewer with a question. These discussions should not be one-sided. A candidate who can read you well will also read your customers well and recognize when to speak and when to listen.

Do your part as the interviewer by asking direct questions, refraining from rambling, and offering concise responses to candidate questions. Brevity encourages the conversational tennis effect to flourish during the interview, allowing the candidate to feel at ease and shine!

9. Be open to new ideas.

Great candidates have strong opinions and are willing to share their views. A candidate once shared with me how much value he saw in the Challenger Sales method and asked if I was familiar with the concept. He attributed this book to his early sales success.

Although the Challenger Sales method wasn’t something my team used regularly, I enjoyed hearing about this candidate's experience with it. If offered the opportunity, the team would have embraced his work style and encouraged him to work in a way that made sense for him.

10. Listen for non-work accomplishments.

Did they complete a 5k? Or receive a certification in a welding class? Whatever it may be, drive and motivation are two traits that usually appear in a person’s personal life as well as their work life. 

Great salespeople have accomplishments outside of work that demonstrate the same soft skills they use to succeed at work. Asking a candidate to share their greatest accomplishment gives you a window into how they plan, research, and execute their long-term goals. A balance of personal and work accomplishments can also be a good sign that this candidate has experimented with methods to prevent burnout and manage stress in a healthy way.

11. Negotiate more than money.

There’s a common misconception that salespeople are only concerned with one thing – commission. That’s simply not true. Plenty of professions are not paid by commission and are motivated by benefits other than money. Great salespeople are no different. Listen for benefits that are important to your candidate and take note of these for the negotiation stage of the process.

Are they in school for a higher degree? Perhaps they’re growing their family? Work within the limits of your benefits package to highlight some perks that go beyond your compensation structure. Professional development stipends and flexible PTO are some examples of benefits your company may already have that can excite a great salesperson who is looking for more than commission in their next gig.

12. Prepare to answer uncomfortable questions.

Showing the courage to ask a hard question demonstrates high confidence and foreshadows how the rep will represent the company in the field. A good sales candidate will ask some hard-hitting questions and they’ll expect thoughtful answers in return.

Be prepared to answer uncomfortable questions like why your last rep chose a different path or what struggles the team is facing. No company or role is perfect, but painting the most realistic portrait of working with your team will be appreciated by any great salesperson. Plus, it’s ultimately up to the candidate to make the best decision using all the information at their disposal.

Find Your Next Great Salesperson

If a candidate possesses eight to 10 of these characteristics, you’re on the right path to hiring them. And if you’re a salesperson applying for a job, you may want to use these interview tactics to get the role.

Finding and hiring the right salesperson is a delicate art, and there’s no definitive blueprint to it. Still, with these tips in mind, you’ll be in a position to bring in qualified candidates and identify which one will be the best for your business.