Stop winging it. Start prompting: The AI playbook for media sales pros

AI isn’t going to shake a client’s hand or build rapport over coffee; that’s still on us. But it will make you faster, sharper and better prepared.”

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

I’ve been selling media for more than 30 years — from print to digital and everything in between. If there’s one truth that hasn’t changed, it’s this: Success in sales comes down to preparation, persistence and relationships. What has changed are the tools available to us.

I recall when research involved examining competing media. Today, artificial intelligence can handle in minutes what used to take hours. And no, AI isn’t here to replace you. It’s here to give you an edge — to help you prepare, add more value and close more deals.

For the past several columns, we’ve covered how to leverage AI in your sales process. This month, we’re summarizing this work, giving you top prompts to leverage. Think of prompts as your new sales scripts. The better you write them, the more valuable and specific the answers you’ll get. Here’s my AI playbook of prompts that can take your proposals, presentations and close rates to the next level.

Pre-meeting research

In today’s busy landscape, you need to know your prospect, their digital presence and where they’re falling short.

Prompts to try:

• “Research [prospect company name]. Summarize their website quality, mobile optimization, SEO, Google Business Profile and social media engagement. Highlight weaknesses or missed opportunities I can mention in a sales call.”
• “Summarize the top five digital marketing trends for [industry] in [city/region] in 2025, with examples of local businesses using them successfully.”
• “List three innovative advertising strategies that have worked for [industry] in cities similar to [client’s city] and explain why they succeeded.”

That’s gold for a first meeting — insights you can bring to the table instead of walking in cold.

Customer persona and competitive intel

You can’t sell without knowing who your customer is and how they stack up against the competition.

Prompts to try:

• “Build a customer persona for a local auto dealer (insert website link) who wants more leads. Include demographics, top purchase motivations, online behaviors and likely pain points.”
• “Identify the top five digital touchpoints for reaching [target audience] and explain how they influence purchase decisions.”

Now you can tailor your proposal directly to what matters most.

Pair competitive intel with competitor analysis

Prompt to try:

• “Analyze the online presence of these three competitors: [Competitor 1], [Competitor 2], [Competitor 3]. Review their websites, social media, search ad strategies, SEO and content strategy. Summarize their strengths, weaknesses and opportunities for [client name]. Focus on website quality, SEO, paid ads and reviews.”

That kind of intelligence positions you not as a vendor, but as their trusted adviser who understands their market.

Proposals, storytelling and objections

Too many proposals read like an impersonal rate card. What closes deals is a story.

Prompts to try:

• “Turn these bullet points into a compelling proposal section explaining how this campaign will meet the client’s goals: [paste bullet points].”
• “Rewrite this list of services into a short, persuasive story showing the journey from the client’s current state to their desired result: [paste list].”
• “Explain this marketing plan in plain language so that a non-marketer could understand its value: [paste plan].”
• “Draft a proposal narrative where the customer is the hero, facing challenges in marketing. Position me as the guide offering a clear plan with measurable outcomes.”

Upload your proposal outline to make this even more specific.

That’s the hero’s journey in action.

Objections

Every sales rep has heard them: “It’s too expensive,” “I don’t have time,” or “We tried digital before and it didn’t work.” Instead of winging it, roleplay with AI.

Prompts to try:

• “List the top five objections a [type of business] owner might have to a [budget/month] ad campaign, and give concise, persuasive responses to each.”
• “Write a rebuttal including relevant data for a client who says: ‘I tried Facebook ads before and they didn’t work.’”
• “Create a confident, positive response to a client who says their budget is too small for multi-platform advertising.”
• “List the five most common objections small businesses have about digital ads and provide empathetic responses that show value.”

This is like having a sales coach in your pocket.

Final word

When I started in media sales, I carried around a briefcase full of rate cards and spec ads. Today, I carry prompts.

AI isn’t going to shake a client’s hand or build rapport over coffee; that’s still on us. But it will make you faster, sharper and better prepared. Use these prompts as your new playbook. Test them. Adapt them. Make them your own. Share your successes with me on LinkedIn. I want to hear from you!

Because at the end of the day, sales hasn’t changed: It’s still about solving problems, building trust and closing deals. AI just gives us a smarter way to get there.

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 here.

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.