Media Sellers Find Their Edge By Turning Data Gaps Into Better Buyer Questions

Every seller calling on a media account now shows up with the same research. AI turns it out in minutes, and the ones who stop there sound alike from one vendor to the next, which is part of why a first meeting is harder to get than it used to be. By the time an advertiser confirms a budget, several sellers have heard it and an RFP is on the way. The opening comes months earlier, when a problem shows up in the data before anyone has named it or paid to fix it. The seller who knows that business best is the one who gets the meeting.

Matt Kiger is the Chief Revenue Officer of Local Media at Townsquare Media, a digital media and advertising company with radio, digital marketing, and live-event properties across the United States. He oversees revenue strategy across the company's local markets and helped build the training program its sellers go through. Earlier in his career, he led digital sales organizations at Citadel Communications and CBS, when a recognizable brand name was often enough to get a call returned. Sellers now have to know a prospect's business well enough to say something worth hearing.

"We have to lean into all the tools. The way to stand out is to own the data and own the knowledge," Kiger says. That means knowing an account well enough to spot what doesn't make sense in the research and ask about it. The answer to that question is something no competitor has.

Open with something useful

Buyers field a constant stream of unsolicited outreach, and leading with a product pitch puts a prospect on guard within seconds. Kiger's teams are coached to start with something the prospect can use. "Make sure that you have business intelligence, a valid business reason, data that is a nickel's worth of free advice for people just to have a conversation," he says.

A seller mentions research pulled on the prospect's industry, says they've worked with others in it, and offers to share what turned up. Kiger calls it a small tweak that opens more doors, and nothing about it requires a better product or a bigger brand.

Sellers who skip that step wait for an RFP instead, which lands after the advertiser has already decided what the problem is and who else to ask. "We need to first have a conversation and get the client talking and expose those pain points. With data, we can probe on the pain points that we already see," he says. Reaching an advertiser before the competition depends on knowing which part of the research to press on.

When sources disagree

Kiger's teams pull data from more than one place. A data science group inside the company gathers it from external and internal sources, and the first thing they check is whether those sources agree. Where they don't, the disagreement itself becomes the thing a seller asks about. "You have to get multiple sources. If they're inconsistent, it all comes down to the question," Kiger says.

The numbers might show that an account isn't winning much mid-market business without saying why, or whether the account sees it that way at all. A seller who asks about that gap learns something the research doesn't hold. Kiger coaches his people to ask openly, saying they've read up on the business and there's one part they can't follow. Business owners like talking about their companies, and the answer usually says more than the original data point did.

The question itself has to come from the seller. "With AI and all the tools, humans need to stand out by being informed and less robotic," Kiger notes.

A prospect who takes a first meeting has usually taken a few others and heard much the same questions each time. What separates one seller from the next is what they ask and how closely they listen to the answer. Both take practice, which has to fit into a week that fills up on its own.

Busy versus productive

Every account base loses business each year, which is why Kiger watches attrition and new business together. By his example, a team that loses 30 percent of its accounts and books 15 percent in new business is shrinking, even though 15 percent sounds like a decent year. Making that up takes more new business than most teams expect, and it starts with how sellers spend the week.

Managers at Townsquare pull up a seller's calendar and often find it packed with client work and meetings, with little time left for prospecting. "Your brain tricks you into thinking that's productive. That's actually busy, and not revenue-generating," Kiger says.

He watches three numbers: discovery calls, since booking one means the seller got in the room, pitches, and closes. The ratio between them, which shows whether those meetings are going anywhere. When the activity is strong and the number still misses, he says that's on leadership. Admin work gets its own slot, and he suggests the end of the day on Wednesdays and Thursdays.

Five years ago, managers could leave a high performer alone and the numbers still came in. That autonomy has narrowed, and managers are now expected to be prescriptive about how the week gets built. "With more competition, more tools, more data, and more AI, we have to be really intentional today," Kiger says.

Reading the room

AI-assisted role play gives sellers a practice partner available at any hour, and Kiger's teams use it for phrasing and objection handling. The other half of the skill only shows up in front of a person, in whether their arms are crossed and their eyes have drifted toward the door. "You have to teach the skill of active listening," Kiger says.

Live practice with another person finishes what the role play starts. Sellers run scenarios until the delivery sounds fluent, and managers are trained to give feedback direct enough to change behavior. A seller still concentrating on the words can't also read the person across the table. The skill improves with reps and fades without them, and it decides whether what a seller walked in knowing turns into a second meeting.

Signals that once took a research team weeks to assemble now arrive continuously, and the work has shifted toward deciding what they mean. Kiger puts the building of that judgment on his managers. "Always be coaching and leveling people up to be better at the discovery, because that's where it all flows from," Kiger says.