2026 TRENDS
By: Shannon Kinney, founder and client success officer, Dream Local Digital
If your sales team is only using AI for prospecting and research, you’re leaving its most powerful potential untapped. The latter part of the sales cycle—when objections hit, deals stall and follow-ups fizzle—is where AI can turn hesitation into momentum. It’s also when it can help you add unique insights and value to your prospect, cementing your role as a trusted adviser.
At this stage, your prospects already know you, your brand and your offering. What they need now is context, confidence, and clarity. And AI, when used well, can help you deliver all three.
Here are four ways media sales professionals can use AI to close stronger, follow up smarter and handle objections with confidence—complete with examples and prompts you can try today.
Role-playing objections: Using AI as your sales coach
The best sales reps know that closing is all about preparation. But most teams “practice” objections once during training or onboarding and never again. In addition, role-playing exercises with peers can feel awkward and forced. AI can change that.
Try this prompt: “Pretend you’re a small business owner who has been pitched a $2,500 monthly marketing campaign with a local media company. You’re hesitant about the cost and unsure of the value. You’re not clear on how these tactics will fuel your success. Challenge me with realistic objections. Then, help me improve my answers.”
AI will push back with the same concerns your prospects do:
“We tried that before, and it didn’t work.”
“That’s not in our budget right now.”
“We’re already doing social media ourselves.”
Then, you can coach yourself (or your team) on better responses—with feedback from AI. Follow-up prompt: “Rewrite my response to sound more empathetic and data-driven while highlighting ROI.”
Use it to create a living objection library—one that evolves with every pitch, campaign or product launch. In my own work with AI, I avoided this stage. Then, in the past few weeks, I’ve been working on this one myself and am already seeing results.
Add context to proposals that convert
Proposals fail when they’re just math and media placements. In many cases, your prospect is confused and unsure how to evaluate your offering. They win when they tell a story of the client’s future success after working with you. AI can help you bring that story to life.
Before presenting, ask AI to help connect your recommendation to a client’s real-world challenge.
Prompt: “Summarize why a local restaurant should invest in a branded content campaign with my company right now, based on current digital advertising trends and consumer behavior.”
You’ll get data-backed talking points that elevate your deck from “What we’ll do” to “Why this matters.” It’s even more valuable when you add the client’s company name and info (website, etc.) and specific goals to the prompt.
You can also use AI to analyze your proposal text for clarity.
Prompt: “Review this proposal for readability. Highlight any jargon or areas where I need to explain the value to a business owner better.”
That’s the kind of prep that makes your proposal meeting feel less like a pitch and more like a partnership.
Emails that add value—not noise
The weakest phrase in sales? “Just checking in.” If you’ve been following this column this year, you know that I consider that the kiss of death.
Your post-proposal follow-ups should demonstrate insight and value, not laziness and impatience. AI can help you craft thoughtful, value-packed messages that get replies.
Prompt: “Write a follow-up email to a prospect (insert company info and industry) who hasn’t signed yet (proposal link here). They were interested in digital video advertising. Include one new industry insight, remind them of the opportunity cost of waiting, and keep it under 120 words.”
You’ll receive something like:
Hi [Name],
I came across a recent Nielsen report showing that local video ad engagement has jumped 18% this quarter — driven by mobile and connected TV. That means your audience is spending more time in exactly the environments we discussed. I’d love to walk you through how our CTV targeting can help you capture that growth before your competitors do. Would you like to reconnect this week?
Short. Insightful. Forward moving.
AI can even help you tailor the tone to each client—analytical for one, casual for another. Always add your human touch but let AI handle the blank-page anxiety. Use it as inspiration to help you add more value to your prospects, making you deeply relevant to them.
“ Proposals fail when they’re just math and media placements. In many cases, your prospect is confused and unsure how to evaluate your offering. They win when they tell a story of the client’s future success after working with you. AI can help you bring that story to life. ”
Build a library of ‘value nudges’
Sometimes deals stall not because of objections, but because of inertia. Everyone is busy, and your proposal could just be sitting in a pile, an email inbox or on the desk. AI can help you create what I call “value nudges”—short, insight-driven updates you can send to re-engage a quiet prospect.
Prompt: “Write a 75-word message for a small business prospect (insert company info) who’s been unresponsive after a proposal (proposal link here). Include one data point or market insight related to their industry that reinforces why they should act soon.”
Examples of what you’ll receive:
“Local search traffic for home services is up 22% this month—perfect timing for your campaign.”
“Meta just rolled out new local ad targeting features. I’d love to show you how we can test them together.”
These micro-messages work because they reframe your follow-up as help rather than harassment.
Putting it all together: The AI close cycle
When you integrate AI into your close process, you’re not automating sales—you’re enhancing it. You’re also empowering yourself to get more valuable work done, deepen your relevance to your prospects, and save time.
Here’s the workflow I recommend testing this week:
- After a proposal meeting, ask AI to summarize the client’s pain points and craft a personalized recap email.
- If you get objections, role-play with AI until your responses feel sharp and natural.
- If they go quiet, send a value nudge with a fresh insight.
- Before final outreach, ask AI, “What would make this offer feel irresistible based on what they’ve told me?”
This combination of empathy, context and persistence—powered by intelligent prompting—will elevate every stage of your close cycle.
Final thought
The future of media sales isn’t just about more tools—it’s about better use of the ones we already have. AI can make every seller a strategist, every follow-up a conversation, and every proposal a story worth saying “yes” to.
It’s not about selling differently; it’s about thinking differently.
So, stop chasing the next shiny AI tool and start training the one you already have to help you close.
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. https://dreamlocal.com/ai-prompt-playbook/
Shannon Kinney brings Dream Local Digital Founder and Client Success Officer 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. Kinney worked with media companies worldwide until pivoting to found Dream Local Digital. Since Dream Local Digital’s creation in 2009, shehas served on the Local Media Association board, received the LMA Digital Innovation Award, appeared on hundreds of stages as a keynote speaker, and helped media companies transform their business model. She also currently serves as a project lead on the Local Media Association Branded Content Project Cohorts, helping media companies transform through new revenue streams. She can be reached at shannon@dreamlocal.com.
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