The real reason media sellers struggle to get appointments

Position yourself as a marketing problem-solver, a local business adviser and a guide through a confusing landscape. When prospects believe you understand their challenges, the door opens faster.”

Shannon Kinney, founder and client success officer, Dream Local Digital

I was asked a great question during a live training this week from a media sales professional:

“How can I get more appointments? Sometimes I have a difficult time even getting in the door.”

If you’re in media sales and you’ve ever thought this, you’re not alone. And the honest answer is: Getting appointments today has far less to do with persistence and far more to do with relevance.

The days of “just checking in,” cold calls with generic pitches, or relying solely on your company's brand or a legacy advertiser list are long gone. Today’s advertisers are overwhelmed, busy and skeptical. If you want their time, you must earn it.

Here’s how I coach sales professionals to do exactly that.

Relevance wins appointments every time

If your outreach sounds like everyone else’s, it will be ignored. Full stop.

The fastest way to get more appointments is to add unique insights and value in every single touchpoint, whether email, voicemail, LinkedIn message, follow-up note — all of it.

Before you reach out, ask yourself:

• Why this advertiser? Why now?
• What value can I add?
• What insight do I have that would actually matter to them?

That insight might come from a trend you’re seeing in their industry, a missed opportunity on their website or social presence, a competitive gap, or a local market signal only a media professional would notice.

This is where AI becomes incredibly useful when used correctly.

AI can help you quickly review a prospect’s website, analyze competitor activity, identify industry trends and draft personalized outreach. The key is that AI doesn’t replace your expertise; it amplifies it. The thinking still must come from you.

Every touchpoint should earn the next one.

Here’s a mindset shift that changes everything: Your goal is not to sell in the first message. Your goal is to earn the conversation.

That means stopping outreach that asks for meetings without context, leads with products or assumes advertisers already understand your value.

Instead, lead with insight. “Here’s something I noticed.” “Here’s what we’re seeing work for businesses like yours.” “Here’s an opportunity you may want to be thinking about.”

When your outreach makes someone smarter or better informed, meetings get booked.

Building the brand of you really matters

This may be uncomfortable for some sales professionals, but it’s critical: You are part of the product.

Advertisers don’t just buy from companies; they buy from people they trust. And trust is often formed before the first meeting.

LinkedIn is one of the most underutilized appointment-setting tools in media sales. You don’t need to be an influencer or post every day, but you do need to show up consistently as someone who understands business and marketing.

Share observations from the field. Comment thoughtfully on local business activity. Post insights from client success stories without naming names. React to industry news with a point of view.

When a prospect looks you up — and they will — your profile should reinforce why meeting with you is worth their time.

Promote expertise, not just media

Too often, sales outreach leads with the platform: print, digital, radio, TV, impressions or reach, but advertisers care about outcomes.

Position yourself as a marketing problem-solver, a local business adviser and a guide through a confusing landscape. When prospects believe you understand their challenges, the door opens faster.

Use AI to scale thoughtful outreach, not spam.

The best sales teams I work with use AI to prep for calls, personalize follow-ups, add insight after proposals are sent and stay consistently visible without sounding repetitive.

The worst use is sending mass messages that feel hollow. The difference isn’t the tool. It’s the strategy behind it.

The bottom line

If you’re struggling to get appointments, it’s not because advertisers don’t need marketing help. It’s because they don’t yet see why you are worth their time.

Be relevant. Add value. Build your personal brand. Use AI to sharpen your insight, not replace it.

Do those things consistently, and getting in the door becomes much easier. And that’s when selling starts to feel a whole lot better again.

I’ve created a free resource for all of you with the best tools for media sales pros, and proven winning prompts for every stage of the sales process. You can find it at https://dreamlocal.com/ai-prompt-playbook/.

Dream Local Digital Founder and Client Success Officer Shannon Kinney brings more than 30 years of experience in leadership roles, developing scalable digital marketing strategies and supporting and training media companies with scalable digital revenue growth. She played a vital role in the development of prominent internet giants, including Cars.com, CareerBuilder.com, Knight Ridder Digital, LinkedIn, Google, eBay and Microsoft. She worked with media companies worldwide until pivoting to found Dream Local Digital. Since Dream Local Digital's creation in 2009, Shannon has served on the Local Media Association board, been awarded the LMA Digital Innovation Award, appeared on hundreds of stages as a keynote speaker and helped media companies transform their business model. She currently also serves as a project lead on the Local Media Association Branded Content Project Cohorts, helping media companies transform through new revenue streams. Shannon can be reached at shannon@dreamlocal.com.