Ask These Questions to Find Your Next Sales Hire

April 8, 2016 at 9:00 AM by Vivek Reddy


The war for talent is so often associated with finding tech candidates (engineering/product/design talent) that organizations frequently forget many of the same hiring complexities apply to finding great salespeople. At any growing company, building out a strong sales team is central to bridging the gap between the product you’ve built and the people who need it – bringing in revenue.

Onboarding salespeople can take time, so it’s important to take a lot of care in your processes for hiring them. Understanding the product, knowing how to build great champions and decision makers, and mastering the environment they’re selling in can take anywhere between three months to a year. Because of this, the hiring risks are much higher – any success takes time to transpire.

How can you minimize risk and find the best salespeople for your organization? I recommend these six questions to help you identify strong candidates.

1. What was your quota and what percentage of your quota did you attain?

This question applies to candidates in any sales role. You’re looking for someone who can show multiple points throughout their career where they consistently achieved their quota, quarter over quarter or collectively over the year. Take a look at what kinds of trends you can find in a candidate’s work background. Do they hit their goals month to month, or does their track record have its slopes with longer periods of ups and downs? Is this person capable of adapting between small, mid, and enterprise-sized companies? Great mid-market reps tend to have more consistent performance month-over-month while enterprise reps will naturally see greater variance due to big buyers’ decision-making cycles. A qualified candidate is someone who can continually meet their quota, but keep in mind their company’s buying cycles when you’re evaluating.

Andreessen Horowitz’s Lars Dalgaard, Founder of SuccessFactors, susses out great sales candidates by asking people to submit their W2s as well as the volume of deals they closed. You’ll learn candidates’ median deal size, which can often give you a more extensive perception of their performance at the company than their average deal size which can be skewed heavily by one big deal. Some may find this tactic intrusive, but Lars argues that the best reps not only don’t mind but relish the fact they can prove their success.

2. How did you rank on your team?

Round out candidates’ answer to the previous question by getting a sense of their performance in relation to their peers. Salespeople constantly finishing in the top 10% of their team’s goals, for example, are likely to do well in a fast pace, high-growth workplace because they can acclimate themselves to a changing sales environment. Understanding how well a rep performed relative to their peers helps to understand how much they made of the opportunities presented to them and really helps to understand their level of hustle.

On resumes, you can look for phrases like “finished 2nd out of 25 reps” or “consistently was one of the top 10% of reps” and you can use reference checking to confirm the validity of those statements. Additionally, look for awards like the President’s Club or Excellence Club which are only awarded to the top reps at an organization. Placing emphasis on this helps to normalize candidates especially if certain sales environments skew too easy (i.e. every rep hits quota) or too difficult (i.e. no one hits quota).

3. Describe your career growth.  

Look for sales candidates with an upward career progression. An ideal candidate with a traditional sales background may have a growth trajectory where they start as an SDR, then grow into SDR lead, AE, and SAE roles. Steady promotions show success and an ability to take on new industries, and is the best proof you can possibly have of someone who’s succeeding over and over again. Consistent promotions show that the candidate excelled regardless of his or her situation within the company and gives you confidence that they can do that within your environment. Oftentimes, this also correlates to a candidate’s ambition, and who doesn’t want to hire ambitious salespeople who consistently outperform?

4. Which projects or initiatives did you drive?

One way to identify a candidate who’s driven, versatile, and will likely do well on your team is to ask about initiatives they lead at their company. Did they spearhead a new project on the team? Were they at the front of the sales team reaching out to a new industry or region? Some examples of internal projects include candidates who were the first reps cracking into the enterprise-level company space, or who evaluated software and tools the team should be using.

Look for candidates with the desire to take on leadership projects, especially those who take on projects outside of our department. (At Entelo, one of our SDRs is working closely with our product marketing team to create a product video.) Another indicator of a reliable, astute candidate is someone who’s involved in the sales interviewing process and has an acute understanding of the well-suited employee the company wants to hire. Lastly, candidates actively involved in mentoring newer or more junior salespeople can be a great sign that this person is ambitious, can be a leader, and has the trust and understanding of the company to develop others.

5. Tell me about your sales processes. Who were you selling to?

All companies have a different sales cycles. A strong sales candidate can articulate the sales processes they’re comfortable with - prospecting, cold calling, emailing, managing agile complex sales processes (selling to decision makers and end users), dealing with legal, finance and procurement, and how they adjusted their processes based on who they were selling to.

Understand which buyer personas candidates are accustomed to selling to, and how that translates to the buyers in your space. Some companies might be looking for candidates selling to decision makers - VP, director-level titles - while other companies are looking for candidates who sell to champions, end users. Calibrate with sales hiring managers to learn the typical buyer persona and who candidates should be familiar selling to. One of the things we focus on is identifying whether someone has had more experience in a bottom-up sales environment (selling to end users and working your way up to decision makers) vs a top-down one (selling to decision makers and working your way to end users). You’ll want to make sure that whichever style they’re accustomed to will resonate with your style of sell.

Less qualified candidates usually have a difficult time articulating their own sales process or they completely neglect or can’t speak to an important part of what you’d consider in your own sales process. I find that this question is open-ended, gives strong candidates a means of showing their expertise, and provides opportunity for follow-up questions to probe other areas of their sales process.

6. What big logos did you close? What was your largest deal?

A qualified sales candidate should be able to tell you about companies they closed. Reps will typically list off logo names on their professional profiles - recognizable brand names are a good sign of wins. Ask candidates to call out their largest deal or favorite deal by company name. Whether it’s sales, recruiting or any other department, anyone that’s been successful should easily and willingly bring up their best accomplishments and you can use that example to understand how they went about closing that deal.

It also may not be a bad idea to look for deal variance depending on the type of sales candidate that you’re looking for. In a startup environment, you may be looking for someone that can show flexibility to close both small logos as well as large ones whereas a larger organization may be looking for someone with a track record of bringing in whales.

Hiring salespeople can be challenging, but using these tactics can help to pinpoint who may be a great fit for your sales environment. What other questions did we miss that help you identify top sales people? Share them in the comments.

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