Considerations When Hiring Your First Sales Leader

Founders of start-ups are often the only ones responsible for sales, but if a company wants to scale, it has to bring on more sales people.?In this two-part series, we’ll cover some of the common concerns that talent acquisition and hiring managers face when trying to add to their sales team.

Assuming you’ve hit the milestones defined by your CEO and Board of Directors, it’s now time to hire a VP of Sales or CRO.??

The type of sales leader you need will depend on a number of factors, but there are some common characteristics every sales leader should possess which should be evaluated throughout the interview process.?

The following questions can help you find a successful sales hire if you’re at the seed stage of your business.?

Sales AE/Manager Interview Questions??

Since this is a very personal decision for both of us, I will be very transparent with you, and I will ask that you do the same if that's okay with you.??

• Start with a tone of transparency, since salespeople tend to oversell during interviews????

Describe your journey from (University, a specific job, etc.) and why you made those choices??

• Their career narratives and reasons for leaving/joining companies should be clear. You don't want to hear: My friend started working there and it seems interesting, I left because my boss was terrible, they changed the compensation plan, etc. Their decision should have been well-thought out.??

??How do you handle sales at X???

• ?Simple question on its face, but they should dig deeper into the way they generate pipelines, the sales methodologies they use and/or that the company prescribes, how they qualify deals, how they handle territories, etc.??

What has been the most challenging feedback you've received and how did it change your approach???

• They should be able to provide concrete examples that show they're not perfect and that they can be coached??

??What three people have had the most influence on your life? Why???

• This is an excellent way to learn about someone on a deeper level and tap into their motivations and desires??

Which manager was the best you ever had? Why? Which manager was the worst and why????

• This gives?you?insight into how they prefer to be managed and/or how they will manage others. You’ll also spot red flags such as “I prefer being left alone to do things my own way, or my manager was an idiot”?

Photo by René Ranisch on Unsplash

Among the following, which is the most important thing to concentrate on (only one correct answer):??

• Closing deals
• Relationship building?
• Pipeline building (the only answer)?
• ?Good reps and managers know that building pipeline trumps everything. ??

We're considering a lot of candidates for this role, why are you the best match based on the company's stage in its growth???

• At the end of the meeting, they should sell themselves to you and close the deal (AKA ask directly for the job or ask if you have any hesitation moving them forward)????

Share your experiences managing teams and how you built them. (Pass if he/she cannot describe how they built a team.)??

• This eliminates people who have only inherited teams or have little management experience.??

Based on what you know, how big a team do you think we need right now? (If he/she cannot answer, right or wrong, then pass).??

• ?What is your current ARR and where would you like to be in 6 months, a year, etc. Then, take the basic math (ARR/quota= number of reps)??

Right now, who do you know who would be a good fit for our sales team? (Good candidates should have a few in mind already.) Give me a little background on them, if not their name.??

• To hit the ground running, any good VP of sales will bring up and comers with them.?

What is the best way to collaborate between sales and client success/management? This will reveal how well he/she understands the customer lifecycle.??

• ??They must understand this to be a leader, as they will be deeply involved in the process of collaboration between these teams.??

What is your experience with sales engineers and sales support? What role are they to play at this stage when capital is finite? (This will show you if he/she can successfully run an early-stage SaaS start-up – and if he knows what it takes to scale once you do).??

• If, in their current role they’ve had a lot of help, they should know that they won’t have that help at an early stage, so how?will?they?cope with that fact???

At this stage, how should sales and marketing work together??

• If he or she understands lead generation and how a lead funnel works, their responses will make it evident. Pass if they provide vague answers.??

Photo by Sammy Williams on Unsplash

Potential red flags to watch out for:??

Did they ask a lot of questions??

• ??They ought to qualify this opportunity just as hard if not harder than a deal????

What did they do to differentiate themselves from other candidates??

• ?Did the interview stick in your mind? Were they able to explain why they would be the best choice for the role at this point in your company’s growth???

How much research did they do about your company before the interview??

• If you’re public facing at this stage they should be able to convey at least a?high level?understanding of your company, an understanding of the market and knowledge of at least one or two of your competitors.?

?In the interview, did they offer excuses, blame others, or criticize coworkers???

• ?The reasons why a deal failed, identifying weak links, or showing lack of collaboration are red flags for reps at any stage of a company’s growth. Selling is a team sport, so successful reps have to interact with a variety of departments within the company.?

Next time, we'll cover specific considerations when building your SDR team to ensure that you have the best possible combination of talent to take your business to the next level.