Why product marketers struggle with sales (and how to fix it)

If your messaging doesn’t help sales win, it won’t get used—learn how to make it indispensable.
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Hi, I’m James. Thanks for checking out Building Momentum: a newsletter to help startup founders and marketers accelerate SaaS growth through product marketing.


The relationship between product marketing and sales is weird. On paper, we’re on the same side. In reality? We speak different languages, operate on different timelines, and have entirely different incentives.

That’s why so many PMMs struggle to get sales to use their messaging. They create positioning that sounds great in a slide deck but doesn’t hold up in a real sales conversation. Sales reps ignore it, not because they don’t care, but because it doesn’t help them win.

If your messaging doesn’t align with how they actually sell; how they engage with prospects, handle objections, and close deals… then it’s useless. A tagline alone won’t move pipeline. A clever framework won’t make quota. Messaging only matters if it helps sales reps do their job better, faster, and with more confidence.

The core issue? Most product marketers don’t think like sales reps. They don’t fully understand how reps make decisions, how they prioritize deals, or what actually happens on a sales call. And if you don’t get that, you’re not going to build messaging and GTM strategies that actually work in the real world.

Sales is a game of incentives and priorities

Here’s what I’ve learned about sales after years of working closely with reps. It’s not a one-size-fits-all playbook, but these patterns have held true for me more often than not.

Sales isn’t just about pitching a product. It’s about constantly weighing tradeoffs.

Incentives shape prioritization

Reps are coin-operated. As Charlie Munger famously said, “Show me the incentive, and I’ll show you the outcome.” Sales compensation is usually tied to quotas, commissions, and short-term sales performance incentives. A rep’s income often depends on hitting or exceeding their target, so every deal they pursue is a calculated risk.

If a prospect looks like a long shot or has a complex buying process, the rep might deprioritize them in favor of lower-effort, higher-certainty deals. If your messaging and GTM strategy doesn’t clearly help them close more deals faster, they won’t use it. Reps don’t just chase leads; they calculate the potential commission impact of every deal, constantly evaluating pipeline conversion rates, and adjusting their focus accordingly to maximize earnings.

Not every prospect is equal. A good rep is always calculating: Is this deal worth my time? Some buyers will close fast with little effort. Others will drag on for months. Reps prioritize accordingly because time is their most valuable resource. 

Time-to-close often outweighs deal size. Depending on your ICP, a quick-win $50K deal is often more attractive than a $200K deal that takes six months to land. Every minute spent on a dead-end deal is time taken away from a more promising opportunity.

Reps don’t have the luxury of chasing bad fits. If your messaging doesn’t help them quickly qualify and disqualify leads, they won’t use it. This is why I recommend being contentious and niche: messaging should make it obvious who is and isn’t a fit.

A sales rep is going to evaluate whether a prospect is a good fit, what their budget looks like, and how long the sales cycle is expected to take. They think about how each deal will impact their commission, factoring in quota attainment and whether the effort required to close a deal is worth the potential payout. If the numbers don’t add up, they’ll deprioritize and move on.

Confidence and credibility win deals

Quota pressure shapes behavior. If end-of-quarter is near and a deal isn’t progressing fast enough, reps will pivot to lower-hanging fruit. This often means shifting focus to existing customers, leaning on discounting, or prioritizing prospects who have shown the most urgency.

Confidence is everything. If a rep doesn’t believe in a pitch, they won’t use it. They need to walk into every call knowing they can win. This belief doesn’t come from blind optimism, but from real, tangible proof that the product delivers results. If they don’t feel equipped, they’ll revert to what feels safe: sticking to familiar talking points or avoiding the pitch altogether.

Confidence is also tied to knowing how to handle objections in real-time. Sales is 30% delivering a perfect pitch and 70% about adapting under pressure to convince and persuade. A rep who feels equipped to answer tough questions, counter competitor claims, and steer the conversation toward the right outcome will sell more effectively. PMMs need to arm them with these insights. It’s not just about the product’s strengths; it’s about how to communicate them persuasively when challenged.

They care about relationships. The best reps see themselves as trusted advisors, not just deal-closers. That means they need messaging that enables valuable conversations. If they feel like their pitch is too transactional or doesn’t align with how they build trust with prospects, they won’t use it. Great messaging helps reps guide buyers, solve their problems, and position themselves as credible experts—not just people trying to hit quota.

Most PMMs don’t account for this. They focus on what to say, but not how a sales rep will actually use it—under pressure, in a live conversation where credibility, confidence, and adaptability matter just as much as the message itself.

How to build for the sales mindset

If you want your messaging to actually drive revenue, you need to build it through the lens of a sales conversation.

One of the most effective ways to do this is to mentally run sales conversations in your head. I do this constantly—predicting how a rep will position the product, anticipating objections, and thinking through how a buyer will react. If you can’t visualize how your messaging plays out in a real conversation, it’s not ready.

Sit in on sales calls. If you’re not regularly listening to how prospects respond to your messaging, you’re working off theory, not reality.

Ask reps what’s working. Forget formal surveys… have real conversations. What messaging do they naturally lean on? Where do they get stuck? Their behavior will tell you what’s useful and what’s fluff.

Build messaging that solves real sales problems. Sales doesn’t need another tagline; they need messaging that tackles real objections, positions your product against competitors, and gives them confidence in every call.

Make it frictionless to use. If your messaging requires reps to memorize a new framework or shift their entire pitch structure, they won’t adopt it. Instead, integrate it into what they already use through battlecards, talk tracks, pitch decks, and discovery call scripts.

Test and iterate. Your messaging is never “done.” Just like sales reps refine their pitch over time, your positioning should evolve based on real-world feedback.

Build like a seller

If you don’t know how a sales call plays out; if you’ve never watched a deal unfold in real time; if you don’t understand how reps think about prioritizing deals, you’re not building messaging that moves pipeline.

So before you finalize your next positioning doc, ask yourself – Would this actually help close a deal? Would a rep want to use this? If the answer isn’t a clear yes, go back and make it stronger.

Great PMMs don’t just create messaging. They engineer it to be so practical, so relevant, and so deeply tied to how sales works that reps can’t afford to ignore it.


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