Let's be honest - hiring great salespeople is one of the toughest challenges founders and sales leaders face. The difficulty isn't just in spotting raw talent; it's in the fact that salespeople are, well, really good at selling themselves. As they progress in their careers, they become experts at knowing exactly what to say in an interview.

This makes it incredibly tricky to distinguish between a potential sales superstar and someone who's just really good at telling you what you want to hear.

What a Bad Sales Hire Costs Your Company

The cost of getting it wrong is astronomical. We're talking turnover expenses that can reach up to 150% of the employee's salary. That includes the obvious stuff like lost productivity and the costs of recruiting and training a replacement. But it also covers the not-so-obvious: lost knowledge, potentially damaged client relationships, and the opportunity cost of what a great salesperson could have brought to your team.

And even when you think you've made the right choice, you might not know for sure for a while. Depending on the complexity of your product or service, it can take anywhere from 6 to 18 months for a new salesperson to fully ramp up.

For those really complex sales cycles? You might be looking at a year and a half before you can truly evaluate if your new hire is a home run or a strikeout.

So, how can you increase your chances of hiring top-performing salespeople and avoid these costly missteps? Don't worry, Pitch Lab has got you covered.

Let's dive into your step-by-step guide that will help you create more certainty in your hiring process.

1. Understand What Drives High-Performing Salespeople

The key characteristic to look for in potential sales hires is what we call "drive." This can be broken down into three components:

Need for achievement
Competitiveness
Optimism

These intrinsic qualities are what separate great salespeople from the rest. It's crucial to understand that you cannot instill intrinsic motivation and drive where it doesn't already exist.

While you can train for industry specifics, sales processes, and techniques, you can't instill drive. It's either there, or it isn't.

2. Screen Resumes Effectively

When reviewing resumes, you’re not (necessarily) looking for industry experience or big company names. Instead look for clear indicators of drive like:

Quantifiable achievements (e.g., "exceeded quota by 120%", "4% year-over-year growth")
Consistent performance over time (e.g., "President's Club 8 years in a row", "Winner's Circle every year")
Career progression and longevity in roles (e.g., promotions, multiple years in the same company)
Recognition and awards (e.g., "ranked #1 out of the entire team")

Here's an example of what to look for in a resume:

"Exceeded revenue target (120% of quota), ranked #1 in the entire team, Winner's Circle 8 years in a row, promoted twice in 4 years.

These elements suggest a candidate with a strong need for achievement and the ability to consistently perform at a high level.

3. Conduct Insightful Interviews

Alright, you've got some promising candidates. Now it's time to really dig in. In your interviews, focus on three key areas as your north star:

1. Assess Drive: Dig deep into their past jobs. Were they promoted? Did they consistently beat quota? Did they make President's Circle? Don't just accept vague answers – ask for specifics and numbers.

2. Would You Personally Buy From Them?: This might sound odd, but put yourself in your customer's shoes. If you wouldn't buy from this person, why would your customers? Always trust your gut on this one!

3. Their Motivation: Here's a biggie – determine if the candidate is running towards an opportunity or away from a problem. Those running towards something are often more motivated and likely to succeed. Be on the lookout for red flags from running away from things like:

Recent round layoffs at their current company
A toxic work environment or boss
Unemployment, and any job will do

Ask questions like:

"Why are you really interested in this role?"
"How does this opportunity align with your career goals?"
"What's motivating you to make a change in your career right now?”

4. Ask Behavior-Based Questions

During the interview you want to move beyond hypothetical scenarios and get to the real deal. The magic phrase here is "Tell me about a time when..." This little gem shifts the conversation from what they think they might do to what they've actually done.

Here are some examples:

"Tell me about a time you received criticism and how you handled it."
"Tell me about a time when you were in a sales slump. How did you dig yourself out?"
"Tell me about a time when prospects were rejecting you left and right. How did you keep going?"
"Tell me about a time when you missed your quota. What did you learn from that experience?"

You're looking for honest, thoughtful responses like:

"When my manager told me my presentation skills needed work, I'll admit, it stung. It took me a few days to really process it. But then I made a plan, got some coaching, and worked on it. I bounced back. I can't do that immediately, but I do work through it."

That kind of self-awareness and willingness to improve? “That's gold, Jerry. Gold!”

Pro-Tip: A great interview is about connection, not perfection. If the candidate you’re interviewing sounds too perfect – like Tom Brady talking to the press after a win – this is a red flag. Usually the candidates who come across as flawless during an interview are the most full of BS with lots to hide.

All great salespeople have some type of personality flaw, quirk, or even a chip on their shoulder that drives them – and the awareness to admit it.

5. Look for Curiosity and Engagement

At the end of the interview, pay attention to the questions they ask you. Great salespeople are naturally curious. They should be firing questions at you about your company, your solutions, your vision for their role. If they're not? That's a red flag, my friends.

6. Assign Light Homework

I know, I know. Homework doesn't sound fun. But trust me, this is where you separate the serious contenders from the also-rans. Give qualified candidates a short assignment after the interview.

Here’s my 2 favorite questions to ask:

Write a short follow-up email reflecting on our interview. What did you do well? What do you wish happened differently?
Identify 5 potential prospects for our product/service and explain why you'd reach out to these 5 first.

This exercise provides insight into their writing skills, self-awareness, and ability to do basic prospecting work. It should take about 20-30 minutes to complete. If a candidate is truly interested in the role, they'll put in the effort.

7. Create a Repeatable Process

Last but not least, don't wing it. Develop a structured hiring process that involves multiple people. This might include:

A clear definition of what you're looking for in resumes
A set of standard interview questions
That homework assignment we talked about
Multiple interviewers in a strategic order to get different perspectives

And please, for the love of all that is holy in sales, never hire based on just one person's opinion. Get your team involved. Get everyone on the same page about what you're looking for and triage effectively.

Expected Outcomes for Your Company

Follow this plan, and here's what you can expect:

✅ Improved retention: You'll hire people who are more likely to stick around and succeed.

✅ Faster ramp-up times: These high-achievers will hit the ground running. And will need less oversight and accountability.

✅ A rising tide lifts all boats: High performers will elevate your whole team's game and improve your sales culture.

✅ The bottom line: More closed deals, more happy customers, more revenue.

There you have it. Your roadmap to hiring sales superstars. It's not foolproof (nothing in sales ever is), but it'll dramatically up your odds of building the right team to help you exceed quotas and drive consistent growth.

Want to learn more about how we can help you hire the right salespeople? Let’s chat.

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How to Hire High-Performing B2B Salespeople