Forabilis CEO Natan Chosnek writes about real GTM situations on his Substack, The Bold Guy, stories from the field that shape how we think about growth. His latest is about a trap we see constantly in B2B tech: companies with strong products that keep losing deals not because of what they built, but because of how they positioned it. We call it the Checkbox Category Trap. Read the story first, then come back here for the GTM breakdown.
Here’s how it happens. A company enters a market, studies the category, and builds messaging that checks all the right boxes: secure, scalable, easy to integrate, enterprise-ready. It sounds credible. It looks professional. And it sounds exactly like every other player in the space.
The trap isn’t bad writing. It’s a positioning mistake. When you build your message around what the category expects, you become a comparison, not a decision. Buyers use checkboxes to shortlist. They don’t use them to choose.
The result: you make the final three, and then you lose. Or worse, you get a “we’ll revisit this next quarter” that never comes back.
What makes this trap so persistent is that it feels like the right move. You studied the market. You matched the language buyers use. You covered all the bases. But matching the category is exactly what keeps you from owning it. When every vendor speaks the same language, the buyer defaults to price, familiarity, or inertia — none of which favor the challenger.
When pipeline stalls, the instinct is to look at the product: missing features, pricing gaps, competitive disadvantages. But more often than we’d like to admit, the product is fine. The message is the problem.
Three signals you’re in the trap:
1. Prospects go quiet after a strong demo. They liked it. They just couldn’t explain to their team why *you* over the others.
2. Sales cycles drag without clear objections. No one is saying no, but no one is moving forward either.
3. Your message could belong to a competitor. Swap your logo for theirs. Does it still work? If yes, you don’t have positioning. You have a description.
The downstream cost is real: weakened sales enablement, longer cycles, commoditized perception, and a team that works harder for results that should come easier. And because the symptoms look like a sales problem or a product problem, the root cause often goes unaddressed for longer than it should.
The move isn’t complicated, but it requires discipline. Stop positioning around what you do. Start positioning around what changes for the buyer when they choose you.
Not “we’re a leading data integration platform” but “your data team ships pipelines in hours, not weeks.” Buyers don’t buy categories. They buy outcomes. When your message speaks directly to the result they’re trying to achieve, it bypasses the checkbox entirely and speaks to the decision maker’s actual agenda.
Don’t match the competition. Make the choice obvious. If a buyer has to work to understand why you’re different, the positioning isn’t done yet.
Specificity wins. Breadth blurs.
The tighter your ICP, the sharper this gets. When you’re clear on exactly who you’re building for and what’s at stake for them, the message writes itself, and sales stops having to work around it. Broad positioning tries to appeal to everyone and ends up resonating with no one. Specific positioning feels like it was written for exactly the right person — because it was.
The Bold Guy doesn’t just cover startups. The most interesting go-to-market challenges happen across company stages:
Each stage has different challenges, different resources, and different definitions of success. The Bold Guy explores all of them.
We worked with the Seemore Data founders to reposition in a crowded analytics market. The product was strong. The messaging sounded like everyone else. Together, we shifted the positioning away from data capabilities and toward a specific, consequential outcome for a specific buyer. The result was messaging that stood out precisely because it didn’t try to cover everything.
With the Upsolver (acquired by Qlik) team, the challenge was different: breaking out of one category entirely and claiming space in another. The product hadn’t changed. The positioning had. The new message gave buyers a reason to see Upsolver not as another tool in the stack, but as the foundation of a modern data infrastructure. New customers followed. So did funding momentum.
With Panaya, the opportunity was hidden inside an existing customer base. The product was being sold as a patch automation solution, a useful but tactical category that kept conversations at the operational level. Working together, we reframed the positioning around security readiness, elevating the conversation to the executive agenda and reactivating a renewal motion that had stalled. Renewals grew from 7% to 40%.
Before your next campaign, next sales deck, or next website refresh, answer these honestly:
For GTM leaders, this is one of the most leveraged investments you can make. Fix the positioning and you don’t just improve marketing — you improve every conversation your sales team has, every piece of content you produce, and every campaign you run. It’s the difference between a growth engine that needs constant pushing and one that builds momentum on its own.
Positioning isn’t a brand exercise you do once and file away. It’s the foundation of your sales motion, your content, your campaigns, and your conversion. When it’s sharp, everything downstream gets easier. When it’s not, you feel it everywhere: in pipeline, in cycle length, in win rates.
The companies that win their category don’t just fit into it. They reframe what the buyer is actually trying to solve and make the decision obvious.
If this resonates, go read Natan’s original story on The Bold Guy. It puts a face on exactly this dynamic, and you’ll probably recognize someone you know in it.
And if your pipeline is moving but deals aren’t closing, let’s talk about your positioning.
The Bold Guy launches with stories that will change how you think about go-to-market strategy. From the startup that discovered their real competition wasn’t other products but spreadsheets and manual processes, to the enterprise company that successfully launched a new product by treating it like a startup within the larger organization.
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