How to hire a salesperson the right way (esp. when your product or service requires a pitch)

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April 4, 2022

Sales is an essential aspect of your business, but it can be very challenging to find the right person for the job. So how do you go about finding and hiring a good salesperson? Here are some best practices you can follow.

#1 – Map out your needs and expectations, clearly

The core concept behind how to hire a great salesperson can basically be distilled down to casting a wide enough net, and then having a good way to filter through and find the person you need. Open sales positions generally get loads of resumes and applications (with only a small minority truly being a good fit) so it’s essential to know what you are looking for, in order to find them quickly. Outline the details of the sales position, and the ideal type of person for it, using these questions:
  1. What types of sales will be involved?
  2. What level of experience do they need? (do they need prior experience with this type of sales?)
  3. What marketing / sales skills will they need specifically? (e.g. email marketing)
  4. What results will be expected of them?
  5. What will be the most challenging aspect of the position?
  6. Is there training or an onboarding period for this position?
  7. Any required qualifications or level of education
  8. What are your deal-breaker? (even better if it’s the type of thing you can gauge from a resume)
Jot these down and then use them as filters to quickly screen a large list of candidates down to the ones that are the best fit, before you even interview them. The goal is to avoid the waste of time of interviewing candidates that are obviously going to be a bad fit based on their resume or application.

2. Write the job listing like a landing page

Now that you have a better idea of who you are looking for, write the job listing as if you were writing a landing page. To attract the best talent, it’s important to communicate what you have to offer as a company, your values, your expectations. Write it so that when your ideal salesperson reads the job listing it completely resonates with them. It’s also great if you can describe the day in the life of a salesperson at your company. Optimize the title for the listing for keywords that your ideal salesperson is likely using to search for these types of positions. Some terms you might consider using, as applicable:
  • B2B or B2C
  • Virtual / work from home / remote
  • Commission-based or salaried or contracted
  • Entry-level or experienced
  • The industry (SAAS, etc.)
Finally, set clear and realistic job requirements. Making sure to include the requirements that will help candidates self-select, without the requirements preventing the right person from applying.

How to screen resumes / applications for a sales position

Screen applicants to invite for the interview Take a pass at screening the resumes and application materials you have, using your guidelines outlined in the first step. You can even create a simple spreadsheet based on your answers in the first section, where you check off which items on the list are in alignment with the application. Ideally your application process was set up in a way that gives you the information needed to initially screen 50%+ of the applications (such as questions they need to answer along with their application). You can even consider sending applicants an email with a short list of questions (if this is important to the screening process, and wasn’t caption in the initial application process). The goal is to get to the next phase (the hiring interview) with a pre-screened shortlist of candidates that you already feel pretty good about. Questions to keep in mind:
  • Did they customize their application, or was it completely boilerplate?
  • Did their answer have thought behind them?
  • (Gut-check & Red Flag Indicator) Do I have a strong negative emotional reaction to this candidate?
You are looking for people that seem genuinely invested in pursuing the opportunity of working with you. Those 3 questions alone can generally screen the majority of applications for almost any type of sales position. A certain percentage of your applicants will proactively follow up with you, often before any kind of interview. In most circumstances, you will want to bump those that do this step to the front of the line (good sales work involves a lot of follow up, after all).

How to interview for a sales position

Sales interviews to help you pick the best

While the details will vary, here are some guidelines and essentials for identifying the strongest candidates for your sales position: Take note of: What do they already know? Have they looked into the company? Do they understand the position? The perfect salesperson needs to be excited to work with you. While this might not happen right away, they need to at least be engaged enough at this stage to have “done their homework” on this opportunity. How do they make you feel when you are speaking with them?  Assuming your interviews are structured in such a way that you have a dynamic conversation with interviewees, feeling the vibe of the conversation and rapport you have with them can be a valuable metric. To some extent it can also be a proxy for how a prospect might feel when interacting with them (in a formal setting). Show them your sales and marketing strategy Ask them for their thoughts or suggestions – while their suggestions probably won’t actually be all that helpful, they will provide an indicator of their understanding of the market, and sales in general. Not to mention the value of evaluating their critical thinking skills as they reason through their answers. Ask thought-provoking questions Ask questions during the interview that require them to think, and answer in a new way that they can’t recite from previous interviews. Do they give your questions a lot of thought? Do they seem averse to thinking and tend to default to a more common, comfortable talking point. Sales job interview questions you might consider asking:
  • Which specific skill involved in this position are you weakest at / would struggle the most with?
  • Walk me through how you’d approach this situation with a prospect…
  • Describe your best sales techniques from your previous sales position? (What worked very well that you did?)
  • How do you handle it if you are rejected nonstop?
  • What questions can you ask to qualify a lead for this product / service?
  • Do you like to talk on the phone regularly?
  • What is your best cold email strategy? 
  • Be honest – how do you feel about jumping in and starting prospecting and working on closing deals? Where would you start?
See what questions they ask The ability to proactively ask good questions is essential to sales, especially the more consultative the sales process is. Do they ask any probing, non-standard questions? Did they ask about next steps? Did they ask about our industry / sales process / product? Do they ask questions they demonstrate they have a proper understanding of things? (Or are they inquiring blindly and asking irrelevant questions) To maximize your opportunities to hear these kinds of questions from your candidates, you can proactively solicit questions about them on specific topics (eg.. “what questions do you have about our sales process / onboarding process / industry?”) Some examples of questions from a salesperson that is generally a good sign:
  • Who is an ideal customer? What are red flags that a prospect is NOT a good fit?
  • Do you pay salespeople commission on renewals?
  • What is the average lifetime customer value?
  • What is your close rate?
  • What issues do you have currently in your conversions?
  • What is the most common reason prospects give for not buying?
  • Who is your biggest competitor that beats us out in some ways, and what are those areas?
  • How long is the average sales cycle?
  • How many customers have multi-year contracts?
  • What is the cancellation / renewal / churn rate?
  • What is an average day like?
  • What is the vibe of the team?
  • What is the most money a salesperson has earned on your team?
  • What are your expectations in terms of performance?
  • What is the revenue for this department / team / region for the last three years?
  • What about XYZ idea….? (they provide an idea)
Have them pitch you (the proof is in the pudding) If the job involves pitching people, have them “show you their skills” by pitching you on something. Now this doesn’t necessarily mean “sell me this pen” – which to be honest would be a silly interview question, but it can be as simple as taking the opportunity to ask them to pitch you on why you should hire them. Or role-play a sales call where you throw out some common questions or objections and they do their best to handle them. If they are persuasive in one way, they will likely be persuasive in other ways. Note: this doesn’t necessarily apply to pens 😉 Don’t wait to follow up with them If they are a great candidate, there’s a good chance they’ll be getting other offers as well. Strike while the iron is hot! Keep them interested in the role by letting them know how well they did, and additional info on what to expect coming up. Stay in touch consistently until they formally start (and beyond). While this certainly doesn’t exhaust the list of best-practices of sales interviews, these guiding principles will at least be a place to start.

Resources to find Your Next Great Salesperson

Now that you have a better understanding of the best practices for hiring a salesperson, where do you start when it comes to looking for candidates? There are many great options depending on your particular needs. Here are a couple resources to get you started:

1 – Gohire

Post a job at Gohire and it automatically gets pushed out through a long list of job platforms to maximize your reach, including Indeed, Linkedin, Monster, Ziprecruiter, etc.

2 –

You can also directly utilize ZipRecruiter, which is one of the largest job platforms, with over 1 million employers have used ZipRecruiter to hire.

3 – Linkedin Jobs

Linkedin Jobs is a powerful tool for listing jobs and finding candidates. It has over 800 million people on Linkedin, and loads of built tools and filters for finding the right candidates. InbounceThis site is for people who love using inbound marketing. They have a very active jobs page that is full of current marketing, development, and sales jobs ready to be filled. The site is visited by people who have a sound understanding of marketing and sales. It’s perfect for tech and software, but anyone could probably find good help there.

4 –

If you’re in the SaaS / software industry or other specific types of startups, Angel can be a great resource for you in particular.

5 – Freelance contractor platforms (Upwork, Guru, etc)

Platforms like Upwork are generally more geared towards working with freelancers / independent contractors. Depending on your sales needs, these platforms might be a good options for you to quickly find as-needed sales contractors while you look for a more permanent hire.

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