Sales and marketing spend a lot of time talking about alignment. It's easy to agree that it matters. It's much harder to make it happen.
Freya Ward has sat on both sides of that argument. Now, as Associate Managing Director at Headley Media, a B2B technology lead generation company working with clients from early-stage startups through to enterprise businesses, she sees the same tension play out inside client after client. She's also a respected voice in the industry beyond her day-to-day client work, speaking regularly at events and on panels, and hosting the podcast, B2B Marketers: Off the Record.
Freya joined the Content 10x Podcast right after we wrapped our B2B content strategy series, adding a sales perspective to many of the themes we explored throughout the series.
In this episode, Amy sits down with Freya to talk about why so many sales and marketing teams stop speaking to each other, what a rejected lead reveals about that breakdown, and the one thing she thinks a broken relationship needs first.
What we cover (TL;DR):
- Why "marketing breaks sales, sales breaks ops" holds more truth than most leaders want to admit
- The kind of sales content that gets used, and the kind that sits untouched on a shared drive
- Lead leakage, the 95/5 rule, and why "not right now" is the most recoverable rejection reason in the CRM
- The stakeholder-persona test in gen-AI to pressure-test your messaging before the real meeting
- Freya's first recommended step for any leader working on sales-marketing alignment: get both teams talking to each other regularly, not just once a year at the sales kick-off
Watch or listen to the full episode below or keep reading for key takeaways on what it takes to fix a broken sales and marketing relationship.
Is "Marketing Breaks Sales, Sales Breaks Ops" True?
There's an old line that gets passed around in B2B: marketing's job is to break sales, and sales' job is to break ops. Charming.
Amy put it to Freya directly, especially given she's worked on both sides of that divide. Freya's take? It only feels that way when everyone's chasing the wrong goal.
If marketing measures success by how many leads they can throw over the fence, sales gets buried. Sales starts rejecting leads and before long everyone's convinced the other team is the problem. Nobody wants this!
Freya's seen it from both sides. When she worked in marketing, she found herself getting frustrated with sales. Then she moved into sales... and suddenly she understood exactly why they were frustrated with marketing. The common thread wasn't the people, but the lack of shared goals.
That's why Freya keeps coming back to leadership. If the goals aren't shared from the top, every team ends up inventing its own version of success, the same problem we explored from a content angle in How Do You Align a B2B Content Strategy to Business Goals?. Shared goals have a funny way of changing the mood. Because when everyone's working towards the same outcome, there's a lot less finger-pointing.
The Content That Enables Sales (And the Content That Just Sits There)
Marketing creates a lot of content. The awkward question is whether any of it is helping sales have better conversations. Freya has a pretty simple way of looking at it.
Product sheets and brochures are useful to have, nobody's arguing with that. But they rarely change anybody's mind on their own.
Case studies are a different story. Especially the ones that sound like real people telling real stories a prospect can see themselves in. They bring proof into a conversation that would otherwise just be a claim, and they're hard for a salesperson to create from scratch, which is exactly why they matter.
Educational content earns its place too, but only when it arrives at the right moment. A report or white paper in someone's inbox with no explanation can feel like homework. But once you tie it back to something they said on a call, it’s suddenly part of a valuable conversation.
Checklists are another favourite. They help prospects benchmark themselves without feeling like they're being sold to. That's a very different experience from another product brochure.
The thread running through all of it is context. A PDF isn't persuasive because it exists. It's persuasive because someone says, "You mentioned this challenge last week. I thought this case study might be useful." Freya also pushes back on the idea that sales should have to ask for better content. Marketing should already be in the loop.
That means sitting in on sales calls. Listening for the questions that keep coming up. Spotting the patterns across dozens of conversations instead of waiting for a request for another one-pager.
It's also a reminder that sales enablement content doesn't have to start from scratch every time. A case study built for a prospect further down the funnel can be repurposed into an awareness piece for someone who isn't ready to buy yet, which is exactly the kind of thinking we covered in our episode on repurposing content across the funnel.
What Is Lead Leakage and How Does It Damage the Sales and Marketing Relationship?
Rejected leads don't always get followed up. Sometimes they just find their way back into the CRM... and stay there. This is called lead leakage, and in Freya’s experience it can often have very little to do with the lead itself. It can often be the case that sales reject a lead, they get passed back to marketing, but nobody logs why or the reason logged isn’t detailed enough.
Her fix is surprisingly simple: make sales choose a reason every time they reject a lead. This could be:
- Ghosted
- No budget
- Went with a competitor
- Not right now
Of the four, Freya singles out "not right now" as the one worth paying closest attention to. Nothing's wrong with the fit. The prospect isn't saying never, they're saying not yet, and that's a very different problem to solve. Rescore them, keep them on your radar across channels, and stay visible until the timing catches up with targeted content campaigns.
It sounds like a small thing, but it's the difference between marketing knowing what to do next and simply guessing. A lead that isn't ready today needs a very different follow-up from one that's already signed with a competitor.
That's also why Freya sees this as more than just a labeling fix. In her experience, sales and marketing rarely run on one CRM, Salesforce isn't built for email, HubSpot isn't built for sales, so most teams end up running two systems by design. The trouble is nobody owns the handoff between them.
Once there’s a clear reason code to a rejected lead, that handoff stops being a black hole. Marketing learns what sales is seeing, and fewer good leads fall through the cracks simply because nobody knew what to do with them next.
The 95/5 Rule: Why Most of Your Market Isn't Ready to Buy
Only 5% of your market is ready to buy at any given moment. Read that again. The other 95% aren’t there yet.
Freya keeps coming back to this because it changes the way you think about content. If almost everyone you're trying to reach isn't in buying mode today, then your job isn't to keep asking for the sale. It's to make sure they remember you when the timing is right.
That also means creating different content for different moments.
Someone who's only just realizing they have a problem probably isn't looking for a product comparison. They're much more likely to spend time with a podcast, an ebook, or a webinar.
Further down the journey, that's when checklists and benchmarking content start pulling their weight. People want to know where they stand before they decide what to do next. As Freya points out, LLMs seem to love a checklist almost as much as buyers do.
She also makes the case for borrowing trust wherever you can. Guest podcast appearances. Co-branded content. Joint webinars. If another brand already has your audience's attention, showing up alongside them is one of the quickest ways to earn some of that trust yourself.
The 5% will always get the fastest attention. The other 95% are tomorrow's buyers.
What Can AI-Powered Sales Call Analysis Tell Marketing Teams?
If you want better messaging, there's still no substitute for listening to your customers. The difference now is that it's much easier to do, something we touched on in How Do You Build a B2B Content Strategy Around Clear Messaging and Positioning? as one of the building blocks of a strong content strategy.
Freya points to tools like Gong, where sales calls are automatically recorded and transcribed. Marketing no longer has to rely on secondhand notes or the occasional chance to shadow a call. They can go straight to the source.
That matters because prospects don't speak the way marketing teams do. They describe problems in their own words, ask questions you might never have thought to answer, and raise the same objections again and again. That's the kind of language you want showing up in your messaging.
It's one of the areas where AI can genuinely save marketers hours of work.
None of that means every AI output can be trusted at face value. Freya is a little more cautious when it comes to sentiment analysis specifically. Some tools will tell you whether a call was positive or negative, but in her experience, that doesn't always tell the full story. So, treat it as a signal, not a verdict.
Where she's less cautious is sales coaching. Feed a call into an internal LLM and it can compare that conversation against company guidelines and company voice, giving reps tips and guidance to help them improve over time.
Her view is that marketing should be learning from those same conversations too. Not to review individual calls or score sales reps, but to look for patterns. What questions keep coming up? Which objections never seem to go away? Where are prospects getting stuck?
Those are the kinds of insights that make content better.
How to Get Stakeholder Buy-In Before You Walk Into the Meeting
Gen-AI can be extremely helpful when it comes to helping you to understand your stakeholders.
When you have a big meeting with key stakeholders getting the deck right is only half the job. The other half is knowing how the people in the room are likely to respond to it.
That's something Freya starts preparing for before the meeting even happens. She takes the presentation she's about to share and strips out anything confidential. Then she asks an LLM to play the stakeholder she has to convince – whether that’s an SDR, a BDR, a VP of Sales, or someone else.
The questions:
- Would the stakeholder buy into this?
- Which points raise questions?
- What would they challenge?
- Where are the weak spots?
Freya also gives the model context before asking for feedback. What's the purpose of the meeting? What decision is she trying to reach? What outcome is she hoping for? Then she'll ask it to score how the presentation is likely to land and explain why. One prompt she comes back to: "I want to get buy-in... I don't want to tell the salespeople how to do their jobs."
It's a simple way of spotting friction before it happens and can be used with all stakeholders, from sales, marketing, finance, leadership, or any part of the business with a different set of priorities.
How Do You Fix a Broken Sales and Marketing Relationship?
For all the talk of AI, lead scoring, content, and CRMs, Freya's final piece of advice was surprisingly simple.
Talk to each other.
It sounds obvious until you look at how many companies manage it. Freya's seen sales and marketing teams go six or seven months without a proper conversation, often not since the sales kick-off at the start of the year.
It doesn't have to be a big meeting, either. Twenty minutes is enough, skip the presentations and make it a conversation. Don't leave it to the VPs while everyone else listens. The people doing the work every day have just as much to add.
If bringing the whole team together feels like too much, start smaller. Pair one marketer with one SDR. Run a pilot campaign. Get a senior sales leader's backing, then let that success speak for itself.
Freya's been on both sides of this long enough to know it rarely comes down to one big fix. Sometimes it's a small process change, like capturing why a lead was rejected instead of just marking it "rejected." One SDR willing to try something different. A twenty-minute conversation instead of a formal review. It sounds simple, but that's often where the biggest changes start.
If your sales and marketing teams could use a nudge in that direction, we'd love to help. Click here and let's talk.
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