
I've been working as a Sales Executive for 9 years. In this timeframe, I've hired other Sales Engineers and I've been hired as well.
Below I provide a window into this process, the mistakes I've made and seen other organizations make, and - most importantly - how to find and close the candidates that will MAKE or BREAK your ability to sell your product.
I'll go through:
Three Red Flags about your candidate AND about your expectations
How to evaluate a Sales Executive
Where / how to find a great Sales Executive
Three Big Red Flags to look out when hiring for sales
Red Flag #1 - Sales Executives able to hit the ground running

“I’m seeking an assertive project manager type who knows what they need from me / the team, and knowing we’re very busy" - Matt Belitsky – SVP, Global Sales & Marketing at Komiko
What I'm pointing out here is that a Sales Executive must first understand your product and what you've done so far. This takes time and it would be unrealistic to minimize this part and expect an efficient collaboration.
A good Sales Executive examines everything on your website, and then wants all your case studies, will volunteer to listen in on your sales calls, and sit down with your salespeople in order to fully grasp how you are currently selling.
Your candidate needs to embrace both your solution offering, and your customers as much as you do. If he’s only dictating a process and doesn’t want to listen or learn about you, that’s a huge red flag (for the candidate this time).
Red Flag #2 - Industry Bellwethers & revenue generated
"(...) I try to make sure the sales consultant or trainer’s skill sets are directly applicable to the business problem I am trying to solve. (...) it’s gotta be super relevant otherwise it’s kind of pointless.” - Dave Hawley – CMO, Silicon Valley
Be wary of pulling staff out of the big companies, the monoliths of your space that you hope to eclipse. These reps work with established marketing organizations that drive lead gen and handle existing contracts that are largely on cruise control. They won't have these luxuries at your company, and that is often a deal-breaker.
Moreover, just because someone sold human resources software before doesn't mean they can sell all HR and recruiting software.
When it comes to industry focus, you might look for people who have sold to the same decision-makers your firm sells to at a similar price point and budgetary cadence.
Red Flag #3 - Only referenced people from my network

“I look for someone who is referred or comes from my network (...)" - Dave Hawley – CMO, Silicon Valley
Sales Executive job is meant to put you in contact with prospects that potentially never heard of your product before. Thus, it doesn't make sense to trust only people coming from your network as well as Sales Executive selling only through their existing network.
The notion of hiring a sales rep for their connections is dying. That said, staff with a lot of existing relationships can be helpful. This should be the lowest-priority quality you look for (by far).
How to evaluate a Sales Executive

Once you know your initial go-to-market strategy is working, it's time to add more people. You increase the number of humans so you can increase the number of calls, emails, demos, deals. Sounds like an assembly line, and it partially is, but humans are more complicated than that so there's nuance to the construction of this revenue factory.
"Your sales staffing should have the same rigor as your engineering staffing." - Peter Kazanjy
This is pretty controversial. For decades, people have perceived salespeople as fairly fungible, coin-operated, cannon-fodder for your march into the market.
Hiring salespeople who barely clear the bar and then firing them when they don't just doesn't work anymore.
Raw Characteristics
Smart: College is a helpful indicator, but should never make someone an automatic hire. Nor should the absence of a top school disqualify anyone. Beyond this, look for a pattern of academic and professional achievements.
Resourcefulness: Look for people who keep figuring things out. Maybe they started a business on their own or are known for clever hacks.
Coachability: No sales rep will be perfect when they first join your team, and there's nothing worse than a rep who thinks they have nothing to learn.
Attention to Detail: Good sales organizations are as much about methodical execution as they are about people and persuasion. Precision follow-ups and organized pipelines are a must.
Persistence: Keep an eye out for candidates who know how to endure.
Positivity: Even a win rate of 35% means you lost 65% of your deals. Remaining upbeat in the face of micro-failures is key. Not all prospects are peaches. Staying kind and courteous is a must. Throughout your screening, pay attention to the tenor of candidates' references and probe into how they handled past failures and challenges.
Teamwork: Individual achievement matters, but if your reps don't know how to share information, feedback, and support over time so your process grows and improves, you're already sunk.
How to evaluate your candidates (examples)
Example #1: mini homework assignment involving account research and voicemail pitching. You can ask candidates to leave a 30-second voicemail pitching your company as if you were a prospect (with a detailed background). This requires the initiative to internalize your firm's value proposition.
With this kind of assignment, you can tease out different levels of execution. Some candidates will abstractly pitch your firm. The tier above will research the prospects' background to tailor the pitch.
Example #2: a quick 30-minute call. It can be very helpful for understanding if the person has the right characteristics. I like to use this time to authenticate their intellectual acumen by discussing funnel optimization and asking them to take me through a lead-generation and sales funnel they're familiar with. They may draw on their current job. Regardless, I try to hit these key questions:
What were the traits of the prospects and how could we find more of them in a scaleable way?
What would lead to a higher conversion of the sales funnel?
How would they ensure that customers were happy with the value being provided?
How could they get sales reps to do more demos in a given period?

Example #3: a simulated qualification call. I tell the candidate to treat me like a prospect that has agreed to a demo. Because this is essentially a mock funnel pass, it's incumbent on you as a hiring manager to pay attention to all parts of the sales and presentation process looking for both excellence and soft spots:
How do they conduct the call?
What pre-call preparation did they do to ensure that they knew about my business?
Do they start with discovery questions?
Are they consultative in their approach?
Do they check in on my comprehension to make sure I'm paying attention?
Are they facile with ROI and business-driver calculations that are pertinent to my business?
Do they build agreement through the presentation?
How do they react when I say I'm confused about something important?
How do they handle my objections?
How do they react to aggressive or even hostile questions?
How do they handle questions about their competition?
Where / how to find a great Sales Executive

In my career, I've successfully tried two main strategies: job posting and direct sourcing.
Job posting
There's an assumption that candidates who are actively answering job posts are only looking because they’re not talented enough to be promoted where they are.
I'd say this is especially NOT TRUE in sales, where people are active networkers, career-minded, and more likely to hop around. They're typically on the lookout for the next good opportunity. So don't discount them.
Moreover, candidates coming through job boards are highly motivated, and thus more likely to make it all the way through the hiring funnel, provided they meet your criteria.
Direct sourcing
You can use common candidate databases like LinkedIn or talent search engines to seek out and proactively qualify candidates. This is great because you can go after the exact characteristics you want.
Tip 1: Salespeople are on LinkedIn constantly.
For this reason, they tend to have extremely up-to-date and well-appointed LinkedIn profiles, often with direct contact information.
Tip 2: Contacting these candidates shouldn't be hard. Sales professionals definitely see their inbound LinkedIn messages. Email and phone are preferable (often available). it will increase your hit rate.
Conclusions
Sales hiring is truly the engine of your organization's revenue success. You need to treat it as such — methodically, aiming for maximum quality of people who are well-matched to your needs and strategy. If you don't give it the time and attention it needs, you're sabotaging any chances you have at winning your market.
Last note:
If you have extra folks who made it through the funnel and meet the bar, hire them. Having more rainmakers is a good thing.
Now that you are here
Holborn is a Sales advisory boutique in London, specialized in supporting high-tech firms in the B2B market development.
The question is: do you need sales done?
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