Digital Ads in 2024: The Challenges of Transitioning Your Team to Digital

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“You can’t teach an old dog new tricks.”

You hear that warning a lot when you plan for the future. I know I heard that plenty when I was a publisher helping ad sales teams transition from a print-focus to digital.

As far as business expressions go, there are few that I disagree with more than that one. Its dismissing message bears no reality on what I experienced in helping salespeople and advertising teams make the leap to digital ad sales.

So let’s dispel this oft-repeated phrase, once and for all.

“New tricks” are the new normal (and that’s good news for skilled salespeople)

Digital ad sales is obviously a new ball game for most salespeople. They are going to have to learn some new technology to place ads with whatever digital provider that you’re using. There’s work involved with targeting, and the increase in targeting flexibility can make ads more complicated to place. They’re going to get asked more often to report and show results, so they’re going to have to get an understanding of digital analytics so they can give clients feedback on their campaigns.

With print, clients are looking for a phone to ring or to increase branding. But in digital they’re almost looking for a tangible response that you are supposed to show them, so you’re working with a different animal than when you’re working with print in terms of expectations.

But chalk that up to relationship-basics, and that’s by no means a “new trick” for a solid salesperson. By putting those relationship and sales fundamentals that do translate front and center, that will drastically help with resistance to the transition. And make no mistake about it, resistance is going to be the first thing you’re gonna deal with.

Resistance to learning new things probably starts as soon as people leave college, and increases for most people as they approach retirement age. Sometimes the resistance is an unwillingness to try new things or a fear of new technology, but more likely it’s a result of people having gotten a good system down for what they do and a reluctance to let go of that. It took them a long time to perfect a pitch and it’s hard to part with something they are good at. But most print salespeople can and will adjust to selling digital products. It is a matter of how long that transition is going to take.

The programmatic digital advertising model isn’t just with websites, but it’s radio, podcasts, video, OTT, all different media formats. Even print is getting more targeted by zip code, and beginning to act a little like digital, so if someone says they won’t adapt to digital at this point, it probably means they’re not going to be in advertising sales.

Transitioning Your Sales Team

Some people are great at selling print and they’re going to have a difficult time picking up on digital. But over time they get the gist of it and they realize how to do it. So it’s a matter of time and familiarity. I wouldn’t give up on the people who do it slowly. They’re just going to have a longer runway time. I have seen numerous salespeople who started slowly but became solid digital producers.

It’s an adjustment, but it’s an adjustment that sales reps of any age can make. In some ways, since they’ve been selling for longer and making micro-adjustments for longer, they can adjust easier. We had plenty of sales reps in their 50s and 60s who were able to pick up and learn the new technology. It may take them a little bit longer, but they’re definitely capable of it. It just requires some dedication and patience and work on your part.

There is an assumption that young sales reps pick up new technology faster than older reps, but my experience is that it’s really about willingness to try new things and change. I have seen seasoned sales reps who adopted quickly and younger sales reps who were slow to transition.

One thing that salespeople old and young respond to is, of course, money. One way I’d jumpstart a digital sales transition is offering a greater sales commission incentive initially for digital. For instance, instead of a 10 percent commission, that first year that they do digital advertising, they’re going to get a 12 percent commission.

Sales reps tend to have a what’s-in-it-for-them reaction. So instead of pitching a digital transition to them by saying it would be good for the company, say, “We think this is an opportunity to dramatically increase your income.” That’s going to resonate with a salesperson..

Knowledge is power … and it also leads to comfort

The key thing to overcoming resistance is familiarity. You’ve got to have a good training plan. And one of the things I recommend doing is looking at resources that are out there.

Fortunately, you don’t have to look too far from right here. Through our own Magazine Manager blogs, we have written two beginner primers on programmatic advertising that are great resources: the first is a glossary of relevant programmatic terms, and the second is a Programmatic Advertising 101 to get your sales reps started.

PMP Jounce Private Marketplace

Source: Jounce Media’s The Little Black Book of Private Marketplaces

Another really good resource is Jounce Media’s Little Black Books, which are great downloadable explorations of topics like real time bidding, walled gardens, native advertising, and more. They are one of the leaders in digital transformations for publishing companies and do a great job of making somewhat complex concepts seem simple.

If you want to accelerate your training plan and bring a pro in to help with your transition, there is none better than Ryan Dohrn of Brain Swell Media and Eric Shanfelt of Nearview Media. Ryan is widely regarded as the advertising industry’s top sales trainer and is a popular speaker who has written books and created countless videos on sales training and digital transformations. Many of our clients use Ryan as a Sales Training and Digital Consultant.

Eric is a former head of digital marketing for several large publishers and is now a popular speaker and consultant on both digital audience development and all things digital marketing. While Ryan focuses more on the sales training side, Eric’s strength is audience and digital strategies. Both are top notch, first-class strategists and motivators.

Part of the challenge of transforming your staff is they have to believe it will work for them, and sometimes an outside consultant gives that “inspiration and motivation” that the same voice they always hear internally might not be able to deliver.

It’s also important to have a good provider who can both provide the programmatic and digital offerings and assist with the training. A couple of digital agencies who are good at not only providing digital inventory but also helping to train your sales staff are AdCellerant and January Spring.

Magazine Manager integrates AdCellerant with its software to simplify digital ad order entry and plans to do the same with January Spring. Both agencies have a variety of digital advertising offerings that will immediately give your sales team more products to sell.

These agencies are good at delivering programmatic ad inventory outside of your site, but in terms of managing inventory on your brand’s website, you might also want to look at Broadstreet Ads. They are similar to Google Ad Manager but have some technologies, strategies, and training capabilities that are more appropriate for small and midsize publishers than Google Ad Manager might be.

In regards to training, you’ve got to set up a program where, every week, you do digital training, answer questions, and go over some part of the digital ecosystem to make the sales team more and more familiar with it. Don’t simply throw it out there and think a couple initial training sessions will get it done. You probably have to have weekly training sessions for 12-16 weeks to get them completely familiarized with the new product, and then answer questions on an ongoing basis.

It’s an ongoing process. And keep in mind the digital landscape is dynamic. It seems like every month there is a new offering, targeting capability or some change from Apple or Google that alters the landscape. You have to accept that staying up to date is part of your new paradigm.

The importance of roleplaying

I recommend roleplaying with people to see what their pitch actually looks like. Let each sales rep do a roleplay on how they would present the digital advertising to you. It will quickly become clear if you’ve got someone who hasn’t dug in and doesn’t understand it.

Some sales reps go into training thinking of it as an imposition, and they never plan to actually make these pitches to clients. If they know that you are going to roleplay with them, they are going to be a lot more engaged in the training sessions. Making them develop a refined presentation will remove any idea that they can just patronize management by attending training sessions, and it will give the confidence that this is really something they can pitch to clients.

Ask questions the clients would ask. What’s it going to cost? How many impressions will I get? What websites can I expect to be on? Are there ways I can target? Tell me how it works. Try to come up with a list of questions that a client is going to ask, and then be prepared to hit them with these questions..

Identify the internal leaders

You may have 10 sales reps and you want them all to go sell it. You’ll likely find that the 80/20 rule kicks in.

The 80/20 rule applies to a lot of things in marketing and in life. And it certainly applies to this as well. That’s where 20 percent of the people are going to generate 80 percent of your digital sales. A couple people will pick up the lion’s share and become so good at it that they become the de facto digital experts within your company.

Companies have tried different strategies, where they hire people who are digital specialists. Others have taken the print people and successfully converted them. Both models have worked for different companies. The best thing to do is to try it and see who’s going to do it.

Once you get someone who’s good at it and making money, that will help get the other people involved. Because they’ll see somebody who’s making money and the leaders within your sales organization will start to teach it. It’s hard when you’re an owner and you’re telling people this is what we’re going to do. When somebody makes it work and starts to find success with it, they’ll start to teach the other people because, well, they love to talk about their successes. This is how I did it, these are my tricks, I figured this out.

When one sales rep begins to make some money selling digital, you’ll see they’ll begin to train each other. You may take someone who’s shown a lot of aptitude and make them your lead. You’re going to need a leader within the company. You can’t have 5 people and none of them are good at it. That’s going to cause a problem. If that happens, you need to get someone external to come in and show people how it’s done. Show them that it can be done, then hopefully the other people will follow.

On a structural level, you’re going to have to come up with a support team or person who helps them with fulfillment so that they can communicate effectively with the client. Unlike print, every digital client may have a customized targeting program, and if that’s the case, then you’ve got to have a team that’s ready to support that. Almost every team that I have seen embrace digital has a good support person who helps explain targeting capabilities, helps with order entry and fulfillment, and provides analytics to the sales team. That’s an additional cost that you are going to need some volume in order to cover.

Digital ad sales really is a team effort, and it’s important for those salespeople just diving in that they know they can find support all around them.

Find the sweet spot for your clients

In addition to finding a good technology partner, training your staff, and building a digital support infrastructure, the last thing you need to understand is your individual clients. Specifically, their sweet spots in terms of advertising expenditures.

You need to understand upfront that spending $500 a month on a digital ad buy isn’t going to work for most clients. It just reaches too few people. Even $1,000 a month is a stretch. Many clients are used to making small buys in print and getting some kind of result, but digital is going to involve larger ad buys.

The sweet spot for most small-to-midsize publishers is going to be $1,000 to $4,000 a month. You have a shot at getting some response for the client at that spending level. It would be great to target clients who can spend 10K a month, but you’ll find that the competition for these types of clients gets fierce. The more they spend, the more you will be up against sophisticated digital marketing agencies who probably have more experience in the arena than you. Most digital ad agencies won’t go after clients who spend less than 5K a month, so that’s usually the sweet spot for most small-to-midsize publishers.

Digital transformation is not a one-time initiative. It’s an ongoing process that involves a lot of patience, training, good technology partners, and understanding where your digital publishing offerings fit in the marketplace. Most publishers start slowly, but within a few years you’ll see digital approaching 50% of your total revenue. And when you hit that mark, you’ll see your company begin to grow at a faster rate as the growth of digital surpasses the decline of print.

About The Author

Mark McCormick founded Mirabel Technologies, a privately owned international tech company, in 2003 with the vision to help publishers streamline operations in an ever-changing media environment. A former publisher with over a dozen successful magazines in South Florida, McCormick introduced Mirabel’s flagship products, The Magazine Manager and Newspaper Manager, as the first web-based CRM made for publishers. Mirabel has since launched Mirabel’s Marketing Manager (an audience development platform), Digital Media Manager (an AI-enabled digital media management platform), ChargeBrite (a subscription platform), and Clean Your Lists (an email verification service), and now serves more than 23,000 media properties worldwide.


The Magazine Manager is a web-based CRM solution designed to help digital and print publishers manage sales, production, and marketing in a centralized platform.

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