Why Your Sales and Marketing Teams Still Don’t Get Along (And How AI Can Help)

If your sales and marketing teams still feel like rival camps instead of one revenue team, you are not alone. I talk to leaders every week who say things like,

“We have the same goals on paper, but it still feels like us versus them.”

In this Strategy Talks episode, I sat down with B2B strategist, author, and AI trainer Pam Didner. She works in complex organizations where sales and marketing are supposed to be aligned, but in reality they are often miscommunicating, underusing content, and feeling nervous about AI instead of supported by it.

What came out of our conversation is this: you cannot fix sales and marketing alignment with shared dashboards alone. You fix it with mindset, structure, and yes, the smart use of AI.

The real reason sales and marketing alignment is still broken

I opened the episode with a simple question that I know is on a lot of leaders’ minds:

“What really breaks down collaboration between sales and marketing, and how do you fix it for real?”

Pam did not hesitate.

“I really think that sales and marketing, we all have a different mindset,” she said.

Here is how she breaks it down.

Sales lives in the middle of the funnel. Their focus is on meetings, opportunities, and closing deals.

Marketing lives at the top of the funnel. Their focus is awareness, demand generation, and nurturing relationships over time.

As Pam put it, marketing leans into relationship building and nurture, while sales carries more of a hunter’s mindset. They are constantly asking, “Do you have a budget? Do you need the tools right now? Should we talk?” If a deal is not moving, they move on to the next target.

None of that is wrong. The problem is that if you let those different mindsets harden into stereotypes, you lose respect and collaboration. Suddenly it is “sales never follows up on our leads” and “marketing sends fluffy content that does not help me close.”

Sales and marketing alignment starts with acknowledging that both mindsets are valid and necessary. You need hunters and nurturers. The goal is not to turn one team into the other. It is to get them pulling in the same direction for the same customer.

How leadership shapes sales and marketing alignment

When I asked Pam if leadership still influences how sales and marketing talk to each other, she literally said, “Oh yeah, certainly.”

At any size company, from small business to enterprise, C suite behavior becomes a template. If the VP of Sales, the CMO, and the CEO talk to each other often and operate in close alignment, you almost always see that mirrored in the teams. If they work in silos, the teams copy that too.

Pam shared that in some more traditional manufacturing companies, sales and marketing barely overlapped for decades and somehow still made it work. That changed with digital marketing.

Now, as she put it, “everything is connected” and the customer journey is fully interlocked across channels and stages. If sales and marketing collaboration does not happen, it creates a very visible gap in the customer experience and yes, it impacts revenue directly.

I even said that out loud in the conversation:

“It can impact revenue directly, correct?”

And Pam did not blink:

“100%. 100%.”

So if you are a founder, owner, or executive, one of the most powerful things you can do for sales and marketing alignment is simple. Model the behavior you want to see. Bring your leaders into the same room regularly. Let the teams see you solve revenue problems together, not in separate meetings.

Turn content chaos into sales and marketing alignment

If there is one place where misalignment shows up fast, it is content.

Pam sees the same pattern over and over. Marketing has a giant list of content:

• Blog posts

• Ebooks

• Podcasts

• Case studies

• FAQs

Marketers know exactly how each piece fits the customer journey. But when sales asks for help, their request sounds more like: “I am sending an email out. I need some content to attach.”

If you just dump a link list into a spreadsheet and send it over, nobody wins. Sales will not use it, and marketing will feel ignored.

Pam’s fix is wonderfully simple.

“Instead of sending the salespeople a list of marketing content, why don’t you classify the contents that you have into sales stages,” she suggested. “Not customer journey, but sales stages. How the salespeople actually move their prospect along.”

Then she takes it one step further.

“We build like a little table. It is a cheat sheet,” she explained. “If you are doing this, these are the type of content you should use. If you are doing that, these are the type of content you can use.”

As a content strategist myself, that made me instantly think of FAQs, research summaries, and case studies. If you put those in the right spots on a simple cheat sheet, sales managers and reps can grab the right asset, attach it, and most importantly, feel like they own it too.

Here is a basic way to start:

1. List your core sales stages in language your sales team actually uses.

2. Take your existing content library and map each asset to one or two sales stages.

3. Build a one page cheat sheet that says, “If you are doing X, use these three assets.”

4. Train sales reps on how to choose and adapt content instead of waiting for marketing to hand them a perfectly packaged email every time.

This is where AI can quietly save you hours. Pam shared that you can upload your content list into a tool like ChatGPT and ask:

“How would you recommend these different pieces of content fit into different sales stages?”

You still need to articulate your own sales stages clearly and you still need your own point of view. But AI can give you a first pass on the mapping so you are not starting from a blank page.

Where AI fits into sales and marketing alignment

Of course, we had to talk about AI directly. I asked Pam how she sees human sales and marketing partnerships evolving now that AI is in the mix.

Her answer starts, again, with mindset.

In her AI trainings, she encourages clients to make one small behavior change:

“If you have any questions, go ask Chat GBT first.”

For years, all of us automatically “went to Google” for every question about tools, acronyms, or restaurants. Pam wants teams to add AI to that reflex. Not to replace search completely, but to expand how they think and explore.

But she also adds a strong warning:

“The answers provided by bot are recommendations. They are not panacea. Please do not take everything they said as if yes, it is true.”

I loved that, because it overlaps perfectly with my own experience. At one point in the conversation I shared that I had uploaded about 20 of my own newsletters into an AI tool and asked it to write in my voice.

One day it spit out something completely flat.

“This is not good,” I told it. “You go back and you read all the instructions and all the old newsletters and make it sound like me.”

Pam had her own version of that story. She admitted she tried to get AI to write an entire book for her. She hired a developer, uploaded tons of her content, tried different prompts and even AI agents for four days. In her words, “forget it.” It did not sound like her and it did not meet her standards.

Her conclusion is very clear:

• You still need to put the skeleton together.

• AI is great at editing a paragraph at a time, not writing your whole book.

• Left alone, it tends to stack “flowery words” that look nice but have no substance.

So where does that leave your teams?

Here is how I would frame it for sales and marketing alignment:

• Use AI to brainstorm, map content, and draft internal resources like cheat sheets and call scripts.

• Treat everything AI gives you as a first draft.

• Edit for voice, nuance, and accuracy.

• Train your teams to push back on AI outputs just like they would on a junior team member.

Pam also reminded me that many companies are already limiting which AI tools staff can use. Some allow only Microsoft Copilot inside the Microsoft 365 suite and prohibit tools like ChatGPT for work. Her trainings are customized around those realities and often focus first on helping individuals use allowed tools effectively in Word, PowerPoint, Excel, and Outlook before moving into shared agents or automated workflows.

AI is not a magic bridge between sales and marketing. It is a third team member that needs guidance, structure, and guardrails.

A mindset shift that makes sales and marketing alignment possible

At one point in our conversation, I brought up something Pam has said before: that marketing needs to adopt a mindset of helping sales win.

She agreed, and then layered in a very practical reality. In most organizations, the sales team is larger than the marketing team.

She joked that she has never seen a company where the marketing headcount is bigger than sales. It is usually the opposite. Ratios of 1 marketer to 10 sales reps are common. In big enterprises, it can be more like 1 marketer to 80 salespeople.

If you are that one marketer, there is no way you can customize everything for everyone. Pam’s advice:

• Decide whether you will prioritize strategic accounts or support everyone at a standardized level.

• If you must support everyone, you have to scale. That means standardizing what you can and teaching sales “how to fish” instead of just “giving them the fish.”

As she put it:

“You give them something that is semi standardized and you have to tell them you need to actually make some modification. Because when you support that many salespeople, you cannot do customize all the time.”

That is the heart of sales and marketing alignment. Marketing commits to helping sales win. Sales commits to using and adapting the tools, assets, and guidance they are given instead of expecting bespoke everything.

AI can help here too. Once you have standardized templates and cheat sheets, AI can help individual reps customize emails, follow ups, and content snippets for specific accounts without pulling marketing into every single request.

Try this sales and marketing alignment experiment with your team

Near the end of the episode, I asked Pam one of my favorite questions.

If marketing and sales had to switch roles for one quarter, with the same goals, same tools, and the same internal pressure, what would each team finally appreciate about the other?

Her answer was both funny and painfully accurate.

“I think they will find that each job, both sides’ jobs are challenging in their own ways,” she said.

She pictured marketers suddenly responsible for closing deals and hitting monthly and quarterly quotas.

“They will be like, what, I only have 30 days and I have to meet a revenue until I get, oh my God. Oh my God. Oh my God.”

On the other side, salespeople will look at marketing and think, “It should not be that hard to write this blog post.” Then, when they actually try to write it, they will find themselves saying, “I do not know what to say.”

Pam’s point is not that you should literally flip roles for a quarter. It is that structured empathy changes everything. Shadowing, ride alongs, and joint planning sessions can give you a taste of each other’s pressures and constraints. That empathy makes it much easier to build processes, content, and AI workflows that truly serve both teams.

Bringing sales and marketing alignment into your next quarter

If you take one thing away from my conversation with Pam, let it be this: sales and marketing alignment is not about forcing everyone into the same box. It is about aligning very different roles, mindsets, and tools around one customer and one revenue story.

To get there, you can:

• Start at the top and model collaboration in your leadership team.

• Acknowledge that sales and marketing mindsets are different and needed.

• Map content to sales stages and build simple cheat sheets that sales can actually use.

• Use AI as a thinking partner, not a replacement. Always edit, question, and make its work your own.

• Standardize where you can, then teach sales to adapt those assets for their own accounts.

• Create opportunities for empathy, whether that is role shadowing, joint meetings, or mini “swap” projects.

This blog is inspired by Strategy Talks with Pam Didner. You can watch or listen to the full episode in right below, and go deeper into her examples, her AI stories, and how she structures trainings for real teams.

If you are a small business owner, founder, or marketing leader, share this with your sales counterpart and ask one question:

What is one step we can take this quarter to improve sales and marketing alignment?

10 smart AI prompts to explore sales and marketing alignment

Here are 10 prompts you or your team can ask AI to go deeper on the ideas in this blog:

• Act as a B2B strategist. Help me diagnose the biggest obstacles to sales and marketing alignment in a company where I will briefly describe our situation.

• Map my content to sales stages. Here is a list of our current content assets and what they are about. Suggest which sales stages each piece best supports and why.

• I lead marketing and support a specific number of sales reps. Give me a plan to standardize content and build a simple cheat sheet they can use in their outreach.

• Write a first draft of a sales email for the stage I specify that uses our existing case study about a topic I will describe. Then list three places where a sales rep should personalize it.

• I want to run a workshop on sales and marketing alignment for my team. Outline a 60 minute agenda that includes mindset, content, and AI.

• Our leadership team is misaligned about sales and marketing roles. Suggest conversation questions I can use in a joint meeting to get everyone focused on the customer journey.

• Create a list of practical ways a small marketing team can support a much larger sales team without burning out. Include ideas for AI assisted workflows.

• I have certain AI tools available at work, including tools I will list. Recommend three use cases for improving collaboration between sales and marketing that respect typical corporate AI policies.

• Help me write a short internal guide for sales reps on how to use AI to customize emails and call notes while protecting our brand voice and accuracy.

• Based on this blog’s theme, suggest five KPIs or qualitative signals that show our sales and marketing alignment is improving over the next quarter.