The default outcome of B2B sales is not winning or losing to a competitor. It is losing to the status quo. April Dunford has worked with over 300 companies on positioning and the data is consistent: vendors lose about half their opportunities to "we just kept doing what we were already doing," and in some companies that number exceeds 80%. The status quo wins because the company's positioning failed to make a change feel necessary.
This is why positioning is one of the highest-leverage activities for any SaaS team, and why it is also the activity most teams get stuck on. April Dunford's guide on Lenny's Newsletter identifies four roadblocks that derail positioning work. This article distills the patterns and adds the operational moves to get past them.
What positioning actually is (and what it is not)
Positioning is not branding. It is not a tagline. It is not the product roadmap. It is the deliberate articulation of what your product is, who it is for, what alternatives a buyer could choose, and why your product is the best choice for that buyer given those alternatives.
A single shift in positioning can mean the difference between a product that flops and one that breaks through.
Most SaaS founders treat positioning as obvious. "We are the X for Y." That sentence is the output, not the work. The work is the cross-functional alignment on competitors, value, and target buyer that produces the sentence. Without that work, the sentence shifts every quarter and the team never builds compounding clarity.
Roadblock 1: Disagreement about what to position against
The pattern
Sales says the competitor is Vendor A. Marketing thinks it is Vendor B. Product believes the real competitor is internal IT teams building it themselves. The CEO thinks the competitor is spreadsheets. Without alignment on competitors, the value prop drifts because each function is defending against a different alternative.
The fix
The prospect's view of competitive alternatives is the only one that matters. Run 10 customer interviews specifically about what alternatives they considered. Not what you think they considered. What they actually shortlisted. The answers usually surprise the team and force a real conversation about which competitors to position against.
Roadblock 2: Pessimism about the product blinds the team
The pattern
Internal teams know the product's gaps too well. They lead with what is missing, not what is strong. "We have to sell what is on the truck," not what you wish was on the truck. Self-aware honesty is a virtue in engineering retrospectives. It is a liability in positioning.
The fix
Run a strengths-only workshop. For 60 minutes, the team can only describe what the product does better than the alternatives. No mention of gaps, no caveats, no "yes but." By the end, the team usually realizes the product has more competitive strengths than the daily internal narrative allowed.
Then move to writing the positioning. The gaps still exist. They just are not the lead.
Roadblock 3: The differentiated value is poorly defined
The pattern
The team can name what the product does. It struggles to name the differentiated value: the specific benefit a buyer gets from this product that they cannot get from the alternatives. Without sharp differentiated value, the positioning collapses into generic claims ("we are faster, easier, smarter") that every competitor also claims.
The fix
For each feature the team thinks differentiates the product, ask three questions:
- Can a buyer get this from the leading alternative? If yes, it is not differentiated.
- If they can almost get it elsewhere, what is the difference (10x better, available without contract, integrated with the rest of their stack)? Be specific.
- What outcome does this differentiated capability produce that a buyer would pay for? Connect the feature to a business outcome.
The features that survive all three questions are your real differentiated value. There are usually fewer than the team expects (2-4 for most products). That is fine. Sharp narrow differentiation beats broad generic value claims every time.
Roadblock 4: The target buyer is too broad
The pattern
The positioning targets "SMBs" or "product teams" or "marketing departments." These are not target buyers; they are segments containing many different buyers with different needs. Positioning that tries to speak to all of them ends up speaking to none of them.
The fix
Identify the best-fit customer profile based on actual conversion and retention data:
- Which customers convert fastest?
- Which retain the longest?
- Which expand?
- Which refer?
The intersection of these is your best-fit profile. Position to that profile. The other segments are bonus, not target. Teams resist this because they fear narrowing the market. The math goes the other way: sharp positioning to a best-fit segment wins faster than broad positioning to everyone.
The cross-functional alignment problem
Positioning fails not in the document but in the meetings where teams disagree about which positioning to use. Sales pitches one version. Marketing writes another. Product talks about a third. The buyer hears mixed signals and defaults to the status quo.
The fix is forcing the alignment explicitly. A positioning workshop with sales, marketing, product, and customer success in the same room. The exercise: agree on the answer to five questions, in order:
- Who is the buyer?
- What alternatives do they consider?
- What unique capabilities do we have vs those alternatives?
- What value do those capabilities produce for the buyer?
- What kind of company best benefits from this value?
The answers go on a single page. Every customer-facing function commits to using that page consistently. Revisit quarterly.
Positioning is not strategy
Positioning is not a product strategy, nor does it set the product's future direction.
This distinction matters. Strategy decides what to build. Positioning decides how to talk about what was built. The two inform each other but they are not the same conversation. Confusing them produces positioning that promises things the product does not yet do, or strategy that drifts based on whatever pitch sounds good this quarter.
The takeaway
B2B positioning fails at the same four roadblocks: competitor disagreement, internal pessimism, vague differentiated value, and overly broad target buyers. Each has a specific fix that requires cross-functional alignment, not solo work. The teams that get positioning right do not win every deal, but they stop losing to the status quo as their primary failure mode. In a market where half of all deals lose to inertia, sharpening positioning is the single highest-leverage move a SaaS founder can make.
