How to Hire Sales Reps: Sales leaders share their best hiring tips

Being a great seller—and even a great sales leader—is a completely different skill set than being a great hiring manager.

But when your job goes from leading a small sales team to scaling up a team of dozens or hundreds of sellers, it’s time to sharpen those hiring skills. 

Instead of repeating the same old sales hiring tips you can find anywhere online, we asked our favorite SaaS sales experts for their most impactful hiring tips on our show, Grow and Tell.

We talked to sales leaders who have scaled up sales teams at Salesforce, Meta, Product Board, Yext, Lattice, SaaStr, Mulesoft, and more about how they did it.

In this article, we’ll share strategic sales hiring advice on topics like:

• analyzing your previous hires
• when to bring in more teammates
• how many reps to hire at once
• what skills and qualifications to look for
• when to hire a VP of Sales

We’ll even provide you with sales role-specific interview questions to include in your hiring process. 

Keep reading to learn more.

What should you look for in your first sales hire? 

Your first sales hire is a crucial team member. They are the person who moves the company from founder-led sales to truly Sales-led sales. 

However, that first hire does not necessarily need to be an expert closer or even a former star Account Exec from a unicorn enterprise organization to see success. (In fact, for newer companies, we highly advise against the latter.)

Hire a Renaissance Rep

Instead, you should look for what Conor Dragomanovich, the Current GTM Leadership Team Member at OpenAI and Former VP of Commercial Sales at Product Board, calls a Renaissance Rep.

“It's somebody that you can interview to understand how comfortable they will be within the constant turbulence that comes with being a founding AE in an early-stage startup. How do they think about problem-solving? And are they demonstrating an active mind? To what extent can they create a process where there is none?” — Conor Dragomanovich (From Founding AE to VP)

Hire a Sales Engineer

We also heard about this type of thought process from Todd Busler, the CEO of Champify. Todd even suggested hiring a sales engineer as your first hire. 

“But the first one, I think a sales engineer has a great background for that. I think it's like courage, systems thinking, and super clear communication. Because you're on the front lines. You're hearing so much feedback that you need to make sure it's getting to the right people.” — Todd Busler (From AE to CEO)

When do you know it’s time to scale your sales team?

If you’re still in founder-led sales mode or you’re considering moving on from just one rep to multiple, it can be hard to determine the best time for scaling up. 

However, these three suggested indicators below are excellent examples of when it might be time to do so.

You have a repeatable win rate

Peter Kazanjy, the co-founder of Atrium, talked to us about waiting until you have a working process in place before hiring your first rep. Peter’s suggestion is that once you consistently see a 15-25% win rate, you likely have the right product, the right presentation, and a repeatable process that you can train someone on. 

“If you know that if ten new opportunities come into the pipe, and you’re probably going to close one or two of them. At that point, now you say, "Okay, great. This now feels like it's packaged or package-able, such that another line chef can sit alongside me. And they can start working with these raw ingredients and see if they can make a soufflé." — Peter Kazanjy (Founding Sales)

Everything is documented

This might seem like a no-brainer, but having assets and templates ready for your first sales hire needs to be a priority. Even a heavy collection of recorded sales calls with different types of buyers can be extremely useful for new team members. Of course, your new hire will refine and improve any assets you give them, but to do so, they need a starting point. 

Peter again talked to us about the importance of documentation in his Grow & Tell episode.

“The assets should be there. A lot of founder sellers skimp on documentation. But having a demo flow in your head is not great. You should have it documented, even if it's just bulleted out. Make sure that you have a sales deck that you yourself were using, even if it's just a discovery deck that's largely for framing. Have those assets ready.” — Peter Kazanjy

Your sales culture is in a good place

A positive sales culture that encourages constructive feedback loops, healthy competition, consistent player coaching, and inspires sales accountability is hard to master. But, it’s easiest in the early days of a sales organization. 

Once you’ve got a team in place that you feel confident about, whether that’s two reps or ten, we highly suggest expanding your team and prioritizing maintaining that culture. 

Bryan Rutcofsky, Current CRO at PuppySpot, and Former SVP of Sales at Yext, talked to us about scaling your team when the culture feels right. 

“So generally, I try not to bring in more than 50% of a sales team at one given time. If I have ten sellers and I want to grow the team, I won't hire more than four or five in one fell swoop. Because I want the voice of ten to train and teach the voice of the five, not have another massive group coming in that can sway the culture and the attitude of the existing team again.” — Bryan Rutcofsky (From First Hire to IPO)

When should you hire your first VP of Sales?

It’s imperative not to rush into hiring a VP of Sales, as an incorrect hire in a role like this can set the company back months or even years. 

According to SaaStr Founder Jason Lemkin:

“70% of SaaS First VP Sales don’t make it to 12 Months. It’s one of the most common, and also most devastating mis-hires in startups.” — Jason Lemkin

According to Recruiting Expert Amy Volas, a general benchmark for hiring a VP of Sales is when a company reaches $1-2M in ARR and has a small team already working on selling your product. She also shared the importance of having a clear value proposition and a market need for your product so that your company can keep up with the growth a VP-level hire can bring. 

Finally, Amy encouraged founders to be ready to give that VP the autonomy they need to showcase their expertise, hire sales reps, and develop sales strategies.

What to consider when creating your hiring process

Hiring processes have changed exponentially in the last ten years. A process that used to take only 2-3 interviews can now range from 4-8 (sometimes even more.) 

With that said, if you set yourself up for success, you can streamline the hiring process and increase your confidence in your hiring decision. Below are some of our favorite tips for hiring salespeople. 

Use a repeatable hiring methodology

Before you start your hiring process, you’ll want to make sure you have a job description, core competencies, outcomes, an interview process, and even, an onboarding plan lined up. 

One way to do this is by following a proven hiring process. We like the Who Method from Geoff Smart and Randy Street. Their method requires hiring managers to decide on both the outcomes and competencies they hope to see from a new hire before even publishing a job posting to source qualified candidates. This helps them ensure they ask questions related to those said outcomes in the respective interviews. 

And of course, a method like this comes with a suggested interview process as well, with about five rounds in place. They even provide suggested questions for each interview as well. 

Something else to consider is including some sort of sales skill assessment round. This is essentially a test to see how solid the candidate’s actual sales skills are. We don’t necessarily recommend asking them to do a mock demo of your product because they are missing so much nuance at that point. But if you can have them do a mock demo or cold call for an existing product they’ve sold, that can be helpful to see as well.

Use third-party vendors to find the best sales reps

We talked to Ben Braverman, former CRO and CCO of Flexport, about his recruitment process. Instead of using internal recruiters, Ben suggests relying on third-party vendors who are experts at hiring sales roles. He believes this is especially important for companies in the first couple of years of building their sales department. 

“I like to use third parties. I have a couple of partners who, I think, charge a very fair percentage of the base. They're able to get me sales candidates within 14 days of starting a search; that is like to a tee what I'm looking for.” — Ben Braverman (Talkin' Sales in a Pickup Truck)

This is also especially helpful because top sales representatives are usually not actively looking for their next sales position and require higher compensation. Expert SaaS sales recruiters normally have existing contacts they can call upon and a very good understanding of the space and the type of person needed for the role you’re looking to fill.

Always hire two sales professionals

Jason M. Lemkin, Founder of SaaStr, pioneered the idea of always hiring two sales representatives in the early days of his company. Now, this is a thought process many sales leaders follow.

The reasoning? While you most likely won’t have the resources to hire a full sales team at once, your backup plan might be just to bring on one at a time. Unfortunately, if you do this, you won’t learn a thing. 

The fact is, you’ll need to test what type of sales representative works best for your organization. In fact, hiring two vastly different sales representatives can be a great way to analyze the role and what it needs in order to meet sales quotas. 

Hire for skill gaps on your current team

This tip comes from Dock’s Head of Sales, Joey Wright: 

Even the best salespeople aren’t experts in every area of sales. So, let’s say that your team is currently stacked with people who are excellent at closing, but you lack individuals who really thrive in outbound. 

Joey says it’s helpful to hire someone like the latter who excels in an area your team currently isn’t as experienced in so that they can provide sales training in this area for the rest of the team.

Also, when hiring someone who has a very different skill set, you can learn and analyze quite a bit from the experience. Jason Lemkin, for example, hired a totally different type of rep for his second hire, and he gained a ton from the experience.

“I learned about new segments we could sell into. About how to sell at lower price points and in higher volumes. I could easily compare and contrast.” — Jason Lemkin

Analyze your best and weakest sales hires 

MuleSoft has a solid reputation for its sales hiring process, and Rich Liu, their former VP of Global Sales, talked to us about some of their best tactics.

One tactic Rich found incredibly helpful was data analysis on their strongest and weakest hires.

“We actually looked at some of our strongest hires historically and some of our weakest hires historically and tried to actually do some analysis to figure out, okay, what were the skill sets? What were the competencies? What were the backgrounds and prior track records that these folks have had so that we can actually inform this not just by using our gut, but actually looking at what the data showed us?” — Rich Liu (Outcome-Based Selling)

This process also showcases why Jason Lemkin’s suggestion of always hiring two sales representatives is so spot on. 

Skills & qualifications to look for when hiring salespeople

Great salespeople need to be consistently evolving and growing in different ways to keep up with the constant changes in buying behaviors. 

That said, there are still some fundamental traits many high-performing team members have that can never be taught. Below, we’ll get into some of our favorite skills and qualifications, both learned and instinctual, to look for when hiring for each job title. 

Sales Development Representatives 

In the current job market, it’s likely possible to find sales development reps (SDRs) with some sales experience. If you can find candidates with even minimal CRM and outreach experience, it’s absolutely a plus! Don’t be afraid to hire someone with no experience who fits perfectly into your company culture and has the determination to make an impact. 

Look for: 

• Proficiency with CRM platforms
• Ability to prioritize outreach based on intent
• A willingness to get creative with cold outreach
• Consistent follow-up skills

“Curiosity, integrity, and grit,” says Dini Mehta, Executive in Residence at PeakXV Partners, former CRO at Lattice. (Crawling Upmarket)

Account Executives

Of course, every sales organization will require different types of sales talent based on their sales cycle, average deal size, personas, outreach efforts, and more. Because of this, the skillsets and qualifications below should help you identify the right candidates for your sales organization.

• Exceptional interpersonal and customer service skills
• Experience within a specific industry, preferably in a sales or customer-facing role
• Strong presentation skills
• Note-taking 
• Tight negotiation and time-management skills
• The ability to close deals
• People with a competition mindset

“That was really what we looked for in people: that we're part of a competition, that we're willing to push to get better for ourselves. Because in sales, you're going to lose way more than you win, and you have to be able to move past that.” - Bryan Rutcofsky (From First Hire to IPO)

Sales Managers

Sales Managers are going to be one of your most important hires. At this point, it becomes key to find someone who is motivational, has experience building an exceptional culture, enjoys coaching and development, likes building systems and processes, and is analytical.

• Advanced CRM proficiency
• Analytical skills 
• Coaching and development
• The ability to create a phenomenal culture
• Radical candor 
• The ability to actively listen and provide feedback

“The value of a leader is the ability to really and truly listen with the right intentions, and ask meaningful questions, and help both the AE and then yourself uncover the productive learnings and carve the right path out.” - Conor Dragomanovich (From Founding AE to VP)

What interview questions to ask for each type of sales hire

Even if you’re following a detailed hiring process, there are always opportunities to ask more in-depth questions. Below, we’ll showcase our suggested questions based on the sales position you’re hiring for. 

Essential sales interview questions for any role

The questions below are perfect for identifying excellent team players, finding sales candidates who have done their research, and surfacing traits like self-awareness, consistent growth, and more.

• What do you know about our company and product offerings?
• Tell me about a time when you collaborated with other team members. 
• Tell me about a time when you disagreed with a teammate. How did you resolve the situation?
• If we asked your manager what your biggest strengths and weaknesses are, what do you think they would say? 
• What’s something you taught yourself recently? 
• What are some pain points in your current role?
• Describe your ideal next role.

Interview questions for SDRs and BDRs

Sales Development Representatives (SDRs) and business development representatives (BDRs) are often new to their careers but eager to make an impact. Focusing your questions more on personality traits, general interests, and career goals will help you identify A players.

• Have you had a sales job previously? If so, tell us more about your experience.
• How do you deal with rejection?
• Why are you interested in sales?
• Where would you hope to see yourself in five years?
• Are you comfortable making cold calls? 
• Do you feel comfortable using social media sites like LinkedIn?
• What sales technology do you have experience with? 
• Are you held to any metrics in your current role? Sales targets, meetings set, referrals, etc.?

Interview questions for Account Executives

Account Executives are more experienced and should have a ton of real-life examples to pull from in their interviews. Many of these questions can help identify candidates who are a good fit for a sales skills assessment interview as well. 

• What kind of sales environment motivates you?
• What kind of sales cycles are you used to?
• Tell me about a recent sale you won and your role in it.
• Walk me through a sale that didn’t go well. What did you learn from the experience?
• Describe a time when you had to sell a product or service when you were a new sales rep. How did you approach the challenge, and what was the outcome?
• How did your sales performance compare to your plan?

Interview questions for Sales Managers

When it comes to hiring sales managers, you’ll want to focus on finding someone who can influence and empower your team. To do so, you’ll really want to focus on leadership questions, communication skills, how they use data and analytics, and past experience growing and developing team members. 

• Describe the sales process at your previous company. What worked well? What didn’t work well?
• How do you motivate your sales team?
• How do you work with underperforming team members?
• How do you currently measure your sales team’s performance?
• What sales tools do you use to help improve the performance of your team?
• What qualities would you look for when interviewing a sales rep candidate?
• How much experience do you have with writing training manuals or other reference documents for sales teams?

Get more sales leadership advice on Grow & Tell

We hope this article gave you actionable tips that help you hire your first, fifth, or twenty-fifth sales hire. 

We have conversations just like these with expert revenue leaders every week on our podcast, Grow & Tell. 

You can subscribe to our show on YouTube, Spotify, and Apple Podcasts to get alerts whenever we release a new episode.