The Great Recruitment: How To Hire Great Ad Sales Reps in 2023

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Heading into 2023, the forecast was pointing to further global ad spend growth, albeit at a slightly slower rate of change.

Growth is good news no matter what year it is. But coming out of the last few years and following so many changes in the workplace, including what many were calling The Great Resignation, perhaps there’s no better time to embark on what I’d like to call The Great Recruitment — an opportunity to bring great, available talent together with 2023’s promising opportunity for the good of your publication.

Over the course of a 25-year publishing career, I’ve hired countless advertising sales representatives. And with a quarter-century of bottom lines to cross-compare these reps with, I’ve honed what I like to think is a sixth sense about what separates even the good reps from the great ones.

Advertising sales is one of the hardest kinds of sales because you’re selling an idea. That prospect of a return. Most sales are around a tangible item, but advertising is a different animal that requires a rep who’s good at selling an idea and a hope that it works. And if the forecasters are correct, there’s quite a bit of hope to be found this year and beyond.

In this blog, I’d like to share my next-level tips for hiring great ad sales reps. Hopefully, this insight might help so that you too can identify your ideal reps while they’re still just candidates.

1. Search within your industry … but don’t be blinded by big names

One of the first things I would look for, obviously, is people who’ve had success as close to your industry as possible. If the main thing you sell is, for instance, print advertising, someone who’s sold print is obviously going to be the best target. However, there are a lot of caveats.

Oftentimes, small-media companies will make the mistake of thinking that if someone worked for a major magazine nationally or for a big newspaper, that automatically translates to a good hire. My experience was that those hires almost always failed. And they almost always failed because the branding of those companies led to a lot of incoming traffic and easier sales.

The top sales rep at a big local paper probably had their phone ringing off the hook. But if all of your sales are outbound sales, do you want a sales rep who can take calls or who is going to make calls?

Look for people who’ve succeeded in similar circumstances. You want people who are willing to do a high volume of outbound calls, so inquiring about how many outbound calls they make on a daily basis is a telling, must-ask question.

In many ways, each new sales rep is starting from scratch to build a business. You want good hunters, not just people who farm the same business they may have booked before.

2. Ask for proof … but focus on the number of deals closed rather than volume or $$$

Don’t be afraid to ask for proof of previous success. Don’t just take their word for it that they were the top salesperson — ask them for reports that would show where they rank amongst the salespeople in their company. Salespeople are more than willing to produce their charts to show where they rank in order to show how good they are. (Not to mention, as an added bonus, it can give you data on other valuable people who might be targets for your company).

Almost every sales organization has a leaderboard that shows the rankings of the sales reps. The volume of sales that they do is obviously important, but it can also be very deceptive. When I was new in the hiring business, I’d get wowed by big numbers. Maybe someone sold $2 million or $3 million of sales for their company. But consider the page rates. If the average cost of their ads was $20,000, that’s a completely different world than the one you’re likely in.

I would focus on the number of deals someone closed per year. That’s a barometer that I cared more about than the total volume of sales they did. I wanted to see somebody who was capable of closing contracts. And if they could do a high volume.

Oftentimes, the best people we could find might work for a coupon company or somebody where they had to go door-to-door, call a high volume of people, and close a lot of deals. If the price tag on their sale was lower than yours, they’re probably going to make more money selling the same volume of contracts with you. So you’re going to be just as attractive to them as they are to you.

3. Look for experience at getting contracts signed … but also at getting doors to open

One of the things I’ve discovered is that if you find somebody who was doing something harder than what you do — whether that’s from a smaller brand, from a company that was a more difficult sell, or from a job that required more cold-calling — they were very likely to be successful with you.

But you want to stick to industries where actual contracts had to be signed. Some sales jobs, like pharmaceutical sales, are more like public relations for their company. They go around and talk about their products, but they don’t have to get the person to sign a contract. So I would look for things where a contract had to be signed.

People who sold phone services — that was an outside industry that required deals to get done. Anything that’s a B2B service, where reps had to call and talk to somebody and convince them to sign a contract, those are the characteristics that you’re looking for.

The hardest part of sales, we always found, was finding someone who could get the meetings. Getting the meeting is harder than getting the actual sale. You can count on getting a meeting from, maybe, 1 out of every 10 people you talk to, whereas you can get a sale from 3 out of every 10 people you actually meet with. You know your product is good enough to sell itself, so that ability to get the meeting is critical.

Anybody who’s done B2B sales is good at getting in the door. Same goes with someone from a telemarketing background, where they have to be good on the phone. If somebody’s good at getting meetings and seems like they can give a good presentation, there’s a pretty good chance they can get the sale.

4. Consider not just who’s in the car … but who’s pushing to ride shotgun!

There’s an old chestnut in sales that asks: Would you want to spend a day in the car with that sales rep? And if the answer is you can’t tolerate being around them, then the clients probably won’t either.

Even though they might have good numbers, you have to look at whether they’re going to be a fit with your company in terms of being somebody that you and others want to work with. So personality is important — someone who’s super-friendly, with a strong charismatic personality who makes a good impression.

The corollary to that, however, is that if they don’t have a competitive edge, you’ve probably got a problem. Fortunately, you can gauge that right off the bat during the interview process: If the person doesn’t ask you for more money, or doesn’t negotiate during that process, they’re probably not pushy enough for the job.

Most of your great hires are probably going to be a little difficult to work with. Because they always want more. All the best salespeople I’ve worked with were pushy in a nice, diplomatic way, but always asking for more. And if they’re that way with me, then they’re going to be that way with the clients as well. Similarly, if someone was pushy in a very abrasive way, that’s the same way they’re going to ask a client for more, and that’s not going to work.

If they come into your interview and say they want a bigger territory or convey other needs in a convincing, attractive, I’m-worth-it kind of way, that’s a good sign. (Of course, you have to ultimately deal with meeting those needs.) But if you meet a sales rep who takes the low salary you offered right away and says they’re delighted, that would raise my eyebrows. If a person is kind of shy and timid, that person is probably not the person you’re going to want.

The very best are going to have a big ego with a cockiness and edge to it. But they’re also going to be good at working with people, and that’s a hard one to find. Because sales reps generally don’t have that last quality.

That’s when you got someone who’s probably your future publisher.

Not a bad turn of events considering you were just looking for your next ad sales rep. 


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