Increase your closing ratios by adding insights and value

With AI, you can research faster, package insights more effectively and deliver ideas that make every touchpoint valuable. The reps who master this skill will stand out, deepen relationships and close more deals.”

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

One of the fastest ways to lose credibility with a prospect or client is to send a message that says, “Just checking in.” Now more than ever, in every single touchpoint, you must add unique insights and value.

The good news? Artificial intelligence (AI) can help you deliver value-packed insights in ways that save you time and elevate your credibility. Over my three decades in media sales, I’ve seen the difference between sales professionals who simply follow up and those who position themselves as trusted advisers. The latter are the ones who win the long game — and AI is your new superpower to do just that.

Here are three ways to use AI to banish “checking in” and deliver real value at every contact, along with sample prompts and tool recommendations.

1. Bring fresh industry insights into every conversation

Clients expect you to understand their industry as well as your own. Instead of sending a generic “just following up” email, consider leading with a relevant trend or data point that directly ties to their business, positioning you as a valued resource.

Prompt to try:

 “Find three current trends in the [prospect’s industry] that impact how they attract customers. Summarize each in one sentence with a stat, source and example.”

Sample output:

“Automotive shoppers spend 60% of their buying journey online before stepping onto a lot.”

Quick Tip: Utilize generative AI to identify potential pain points that businesses in specific sectors may face. For example, prompt it with: “What are common marketing challenges for a local restaurant, and how could a mix of targeted digital ads and community newspaper presence help solve them?”

That kind of insight makes you a trusted consultant, not a salesperson. It’s not fluff; it’s credibility — and prospects notice.

Best tools: ChatGPT for quick synthesis, Perplexity or Gemini for citations and fact-checking, Google Alerts for continuous monitoring.

2. Use competitive intelligence to spark action

Prospects love to know how they stack up. With AI, you can quickly show them where they’re ahead or falling behind.

Prompt to try:

 “Compare the online presence of [prospect business] with their top three local competitors [insert competitor businesses]. Focus on website quality, social media engagement and reviews. Suggest two opportunities where my prospect can gain an advantage.”

When you share competitor intel, you position yourself as someone who has their back — and create urgency without pressure.

Best tools: ChatGPT (structured prompts), SEMrush or Similarweb (complex data) and social listening tools like Sprout Social or Hootsuite.

3. Deliver custom campaign ideas that inspire conversation

Instead of chasing prospects with, “Do you have time to connect?” Why not send them a spark of inspiration? AI can help you brainstorm campaign ideas tailored to their goals.

Prompts to try:

 “Generate three creative campaign ideas for a [prospect’s industry] business that wants to increase brand awareness and sales. Suggest platforms, content types and calls-to-action.”

Or

“My prospect is [Company Name], a [type of business, e.g., ‘local hardware store’] that primarily relies on foot traffic. Based on my research, they have a basic website but no active digital advertising. What are three key digital marketing strategies they could implement to increase local awareness and drive in-store visits, and what are the primary benefits of each?”

Even if they don’t buy immediately, you’ve demonstrated you’re thinking about their growth.

Best tools: ChatGPT for campaign brainstorming, Jasper for ad copy, Canva for visual mock-ups.

Final word: No more ‘checking in’

Your clients don’t need another vendor who clogs their inbox with meaningless follow-ups. They need trusted advisers who bring insight, context and ideas that move their business forward.

With AI, you can research faster, package insights more effectively and deliver ideas that make every touchpoint valuable. The reps who master this skill will stand out, deepen relationships and close more deals.

The next time you’re tempted to send a “just checking in” message, don't. Instead, use one of these prompts to deliver real insight and remind your prospect why you’re the partner they can't afford to ignore.

I’ve created a free resource for all of you, featuring the best tools for media sales pros and proven winning prompts for every stage of the sales process. You can find it here: 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 such internet giants as 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 inception in 2009, Shannon has served on the Local Media Association board, received the LMA Digital Innovation Award, delivered keynote speeches on hundreds of stages, and assisted media companies in transforming their business models. 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.