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The 7 Keys To Spotting Superior Sales Talent

By Christopher Steiner  •  May 4, 2017

Telling the difference between an elite salesperson and one who will prove below average can be tricky. Things that many people assume to be strong signals with sales people—gregariousness, competitiveness, willingness to pick up the phone—don't always prove out.

My co-founder and I hired about half a dozen salespeople at our startup. If we had been asked to rank each hire by his or her predicted productivity, there's little we would have been right about.

That's partly a reflection on our own judgement. But having talked to many founders about the subject, I've found that most find the task of picking the best salespeople to be somewhat inscrutable.

But there are signals and indicators that can be helpful. And that's what this piece is about. Every industry is different, of course, and requires varying considerations. What's appropriate for a SaaS company marketing to startups and small businesses might not be for a software company that's aimed at enterprise clients. Levels of required experience or domain knowledge might differ in these kinds of scenarios, but some indicators that signal true sales talent will shine through and should be considered relevant in both cases.

With that being said, what follows is a collection of knowledge that has been collected from my own observations as a founder, and from others here at FundersClub, as well as from a wealth of sources within our network.

This is exactly the kind of resource I would have wanted to consult when we were hiring our first sales team members a few months after exiting Y Combinator.

If you read nothing else, read this summary on what the best sales hires look like:

  • Dazzle is fine, grit is better
  • The best salespeople are time management masters
  • You want somebody who is looking for jobs in sales, not just somebody looking for a job at a cool startup
  • The best sales candidates, as the case with most good candidates for any opening, likely already have a job
  • Elite sales talent has empathy for the customer and understands the problems she's seeking to solve
  • They're comfortable conforming to others' systems - half of sales now is following and documenting a process with software
  • Even mediocre salespeople can be fabulous at selling themselves - founders have to dig down on the resume, and look for a track record

Dazzle is fine, grit is better

We often assume that the best salespeople possess magnetic personalities, that they're the most popular person in the room and that their personality lends itself to selling. Being a gregarious, likable person is fine, but it's not a great indicator of who will perform well as a salesperson for your startup. Selling software or services isn't like soliciting bids at a flea market; it requires a different set of skills.

The sales reps who perform the best on modern sales teams are often the ones who are the most organized, most efficient, hardest working, and who are able to get leverage from technology, says Steve Benson, CEO of Badger Mapping, which makes software for field sales reps.

"I call them the 'gritty reps,’” Benson explains. “All of these characteristics amplify the results that a salesperson is able to make.”

The sales reps with great personalities might get a 10% bump in performance from their natural ease with people, Benson says, but a gritty rep might surface 40% more leads by doing more prospecting—leading them to 15% more sales overall. The same grit might lead this salesperson to better utilize technology, allowing them to better manage their time and get 20% more done in a day compared to a normal rep.

Benson points out that, in his experience, gritty repd tend to work a few more hours every week, which also translates to more throughput. All of these things compounded on each other can make a huge difference, perhaps 40% or more.

When trolling for new sales talent, founders should be looking beyond the obvious traits such as intelligence, role related knowledge, and leadership experience. These things are good, but it's more often the case that sales outperformers also possess grit, creativity, and the ability to understand a customer’s businesses and business problems.

The best salespeople are time management masters

Clearly, people with superior time management skills make for better hires at any position within a company. It's especially true in sales.

At my company, we had many quarterly results that surprised the sales staff as well as me and my co-founder. We had notions of who our top salespeople were based on their experience, the depth of their contact lists and their manner in personal interactions. As more time passed, it became clearer that those latter things didn't matter as much.

What did matter: being efficient, reaching out to as many prospects as possible, and being creative in finding and reaching people. This doesn't mean being programmatic and hammering people with email campaigns that are transparently homogenous and non-unique. These kinds of techniques are ubiquitous now in a world awash in SaaS startups.

We sold our company two years ago and I'm still bombarded with SaaS pitches—to my personal email address, trying to sell to a company that was acquired—that basically all sound the same.

The people with the best nose for sales in the current environment find ways to stick out and get noticed—to have their pitch resonate when so many others don't. Doing this takes time, however, and the people who best use their time are more likely to be able to do it.

So how do you spot these people?

Eliot Burdett, founder and CEO of Peak Sales Recruiting, recommends sussing out this trait during interviews, by asking candidates to provide examples of how they use time to their advantage. People who are bent on squeezing the most out of their days will likely be able to immediately recount their strategies.

It's also helpful to ask them how much time is split between prospecting, working the funnel, and closing accounts. Their answers here will reveal how much they value time and how it directly affects their capacity to sell.

"Ask any great salesperson how they structure their day and you'll hear a fairly explicit system for time management and personal organization," says Alex Mann co-founder and CEO of ClickTime, a SaaS tool for tracking the time and work of part-time and contract employees.

You want somebody who is looking for a job in sales, not just somebody looking for a job at a cool startup

Many of the people in the latter group will try and tack out of sales into other areas they might prefer. There's nothing wrong with that, but if they're focusing on different skills and different areas of the company when they're supposed to be selling, their performance, and your company's performance, will suffer.

It's true that most people in sales aren't dreaming about the profession when they're 19. So for founder hiring for entry-level sales positions, it's understandable if candidates have a dearth of experience.

But founders should also be aware of the fact that some non-technical people see sales as the easiest way to get on with a startup. And startups, especially well-funded ones that have achieved some level of buzz—ones that have just emerged from Y Combinator or raised a healthy series A—are seen as highly desirable destinations by fresh college graduates and other Millennials.

People will talk themselves into anything to get aboard a startup that they see as desirable. That means that people will talk not only you into thinking that they're primed for a sales role, but they'll also talk themselves into it. Once this kind of candidate has been on-board for six months, however, it's likely that their lack of zeal for sales is going to show through.

Their work ethic and sense of duty might drive them to do the job as instructed, but founders will not have found a rainmaker, and employees like this will quickly be looking for jobs at other startups doing what they actually want to do: marketing, project management, customer satisfaction, or whatever it might be.

In short, candidates who seem to be getting into sales from out of nowhere should be met with a healthy amount of cynicism.

The best sales candidates, as the case with most good candidates for any opening, likely already have a job

This should be rather obvious, but it's a fact worth including. My co-founder and I definitely saw a correlation between the quality of candidates who were working and those who were not. We hired both, and had success with both, but our best salespeople were almost always hired away from somewhere else.

People with a true knack for selling rarely want for work—so most of them will have to be hired away from somewhere else. Anybody who has been with a company when a top salesperson has defected knows the scramble that can ensue when the person is lost. Often there will be all kinds of last-second efforts to retain the salesperson: big raises, bonuses, promotions—but usually it's too little, too late.

The real question that comes with this advice: how do you find these people who still have jobs and may not be applying for yours?

Doing this is sales unto itself. The best way is to ask people already at your startup for intros and contacts to the best sales talent they know. When that option is exhausted, it can be helpful to enlist the services of a headhunter. You'll want them to do all of the outbound lead generation that finding already-employed salespeople takes.

It's best when a headhunter can be referred to you by somebody who has used their services more than once. We used several at our startup, and there was one in particular with whom we had a great deal of confidence. Headhunter services can be expensive: 20% to 30% of a hire's first year of salary, but for startups in rapid growth mode that aren't big enough to employ somebody on staff to head up recruiting, it's a deal that can work out.

Elite sales talent has empathy for the customer and understands the problems a customer seeks to solve

Any decent sales team member learn everything about her company's product and be able to preach to all comers about its virtues. The sales end of a startup operation represents its frontlines; these people must know the features and uses of the product intimately.

That's the minimum requirement.

The best salespeople don't only know these things, however. They also listen to prospective clients' needs closely, and they empathize with exactly it is that they're looking for or what will fix their problem.

Some sales people listen, but then simply go to their semi-rehearsed speech on a related feature and push that information back out at the prospect. The best salespeople listen and then talk about the problem and the solution from the client's point of view, and explains things in a manner that Rafe Gomez, the co-founder of VC Marketing, which creates content for sales and support operations at companies, refers to as the what's-in-it-for-me method of closing.

“Too many people in sales focus on the features of what they're selling, and not the benefits,” Gomez says. “You want somebody who will research and intuitively understand the needs of a lead or prospect.”

Mark Donnolo, Managing Partner with SalesGlobe, advises that founders look for sales team members with problem solving capabilities.

"Most sales people are friendly and chatty, but do they have the ability to listen and understand the customer’s problem?" Donnolo asks.  

Donnolo recommends using what he calls behavioral interviews to determine a candidate's problem-solving ability. Ask them: "How have you solved problems in the past?"

Or give them real-world examples that your company has dealt with—and ask the candidate what they would have don in the same situation.

"You're trying to observe their thinking and problem solving process," Donnolo says.

The best salespeople are focused not only in acquiring customers, but keeping them

The best salespeople understand how their individual CAC (cost to acquire a customer) affects the company’s performance and how their front-line interactions with customers impact CLV (customer lifetime value).

"These are critical and underutilized metrics for most venture-backed SaaS companies that have relied too heavily on investor largesse for too long," says Cory Capoccia, president of Womply, which makes BI SaaS for small and medium-sized businesses.

In larger startups and companies, the job of customer retention and support is usually passed off to other people after the sale is made. But that doesn't meant the salesperson has to drop out of the relationship. Sometimes the bond made during that sales process is important, and it can be beneficial to both sides if the point person sends the client a little note once in a while, which makes the client feel a little less like just another kernel in the SaaS sales crop.

Good sales hires are comfortable conforming to others' systems - half of sales now is following and documenting a process with software

Lone rangers, people who do things their own way with their own systems, can be good salespeople, good talkers, and even hard workers, but they can snarl a company's sales process and future ability to follow up if they don't use the tooling that's been set up by the company.

Programs such as SalesForce are ubiquitous now within sales, and it's likely that most startups will require sales hires to pull the levers on multiple layers of SaaS when properly executing their jobs. People who easily get exasperated with such things or who are resistant to change—which often comes in the form of software—may not be a good fit.

There's two big reasons that companies so heavily track leads and prospects through burly software, much of which isn't cheap. First - it's usually a more productive way to sell; fewer prospects fall through the cracks and follow-ups are more regular. Just as important, however, is the fact that now the company owns the leads and information, and it doesn't walk out the door when the sales talent does.

This is major shift from how things worked in most environments 20 years ago—and any sales hire that's resistant to getting fully on board the chosen systems of a startup isn't worth bothering with.

When a startup is being considered as an acquisition, one piece of diligence on the acquirer's end often involves investigating the CRM and sales documentation process. An acquirer will want to know that everything has been tracked and documented well so that big pieces of the sales pipeline aren't necessarily lost if certain people are lost.

Even mediocre sales talent can be elite when it comes to selling you on them - don’t be overly impressed by smooth interviews

The list of people fooled by sales candidates who were superbly smooth in an interview, but not diligent or overly productive on the backend is a long one.

To not make that mistake, founders need to be serious about talking to references. You should assume that supplied references will turn up people with good things to say. It’s better, however, if hirers can work their way to other references and people the candidate may have worked with but didn’t list as a reference.

Calling a current employer or clients, however, can be unethical, as doing do could upset the candidate’s current work situation unnecessarily. So try and use the networks of sales staff who are currently with the startup to reach out and talk with people in similar circles who may know the candidate’s work.

If that doesn’t work or isn’t possible, ask the candidate for more references, as many as six or seven total, including past clients. Ask clients how the candidate met them, how they moved them through the sales process and how they compared to competitors’ salespeople.

In the end, founders want to determine that this person has a premium skill set to pair with the startup’s own premium product.  

Christopher Steiner co-founded ZRankings, and Aisle50, YC S2011, which was acquired by Groupon in early 2015.