One company operated in a crowded global payroll market where buyers already understood the category. The other was building a new category around macroeconomic intelligence in Nigeria. Same product marketing discipline, completely different strategic playbooks.
These were RemotePass and Stears, two companies I worked with directly. The contrast between them highlights one of the most important decisions a PMM can make: do you compete within an existing category or create a new one?
Many teams get this wrong because they choose a strategy before understanding how buyers think about the problem.
The first mistake is forcing differentiation for the sake of differentiation
A company rewrites its positioning because a competitor says one thing, so it decides to say the opposite. Another changes its GTM motion because a rival found success with a new approach. Either approach creates reactive positioning that lacks substance.
And as April Dunford argues in Obviously Awesome, positioning is about defining the value you deliver to a specific customer better than anyone else. Effectively, strong differentiation comes from an advantage customers care about, not from simply taking the opposite side of an argument.
The second mistake is trying to create a category when buyers already understand the market
Instead of helping customers make a choice, the company first has to convince them to rethink how they see the problem. That adds friction to every stage of the buying journey. Sales cycles become longer, messaging becomes harder to land, and marketing spends more time educating than converting.
Both traps share the same root: teams choose their strategy before they understand where their buyers are in their awareness journey.
What counter-positioning requires
The RemotePass situation
By the time RemotePass entered the market, companies like Deel and Remote had already established themselves as category leaders. Buyers understood the problem, knew the available solutions, and had a framework for evaluating providers.
Competing head-on would have meant playing by the rules those companies helped create.
Instead, RemotePass focused on a segment whose needs were not being addressed deeply enough: companies hiring across the EMEA region. These businesses faced complex compliance requirements, varied employment regulations, and operational challenges that demanded a more localized approach.
The edge that made the strategy work
RemotePass wasn’t simply claiming to be different. It offered advantages that mattered to a specific group of buyers, including stronger regional expertise, more flexible contract management, faster payment experiences, and benefits tailored to distributed teams.
More importantly, those advantages addressed the real friction buyers were already experiencing.
Three conditions made this positioning credible:
- Buyers already understood the category and did not need to be educated on the problem.
- RemotePass could demonstrate meaningful advantages for a clearly defined segment.
- Prospects were actively evaluating alternatives and looking for a provider that fit their needs more closely.
When those conditions exist, counter-positioning becomes a powerful way to focus attention on your strengths rather than compete across every dimension.
What category creation requires
The Stears situation
Stears began as Stears Business, an economics and business publication. The challenge was that buyers naturally compared it to existing media brands such as TechCabal and Techpoint.
That comparison created a ceiling.
In the media category, Stears would have been evaluated on the same criteria as established publishers with larger audiences and longer histories. The opportunity wasn’t to become another media company. It was to define a different market altogether.
Why category creation made sense
Stears repositioned itself as a data intelligence platform serving institutions, investors, and decision-makers seeking deeper insight into African markets.
The shift mattered because the value proposition was fundamentally different from traditional business media. Here, customers were not paying for news coverage, but for decision-making infrastructure.
As Christopher Lochhead writes in Play Bigger, category leaders shape how buyers understand a problem before competitors enter the conversation. That was the challenge facing Stears. Explaining the product required explaining a new way of thinking about African market intelligence.
The conditions that justified category creation
Several signals suggested category creation was the stronger strategic choice:
- Buyers lacked a clear category for evaluating solutions like Stears.
- The use case was distinct enough that existing market labels created confusion rather than clarity.
- Positioning against media companies would have anchored the business to a market it was trying to outgrow.
Category creation requires education, patience, and a longer path to adoption. But when existing categories fail to capture the value you provide, creating a new frame can unlock opportunities that competing within an established one never will.
The Compete or Carve framework
Before any positioning decision, run these four questions. The pattern in your answers is usually more revealing than a full competitive audit.
1. Do buyers already have a category in mind when they discover you?
When RemotePass entered the market, most buyers already understood the idea of global payroll. Deel and Remote had helped define that mental frame.
With Stears’ early institutional audience, there was often no ready-made category to file it under. Buyers were still interpreting what the product even was.
That difference matters because category familiarity shapes everything that follows: messaging clarity, sales cycles, and how quickly trust forms.
2. Do you have a clear, provable advantage on dimensions buyers actually care about?
Positioning only works when it can survive a sales conversation and basic buyer diligence.
In practice, this means your advantage should show up in observable ways: product depth, performance metrics, compliance coverage, integration speed, or domain-specific capability.
For example, RemotePass can point to tangible strengths like contract workflows, payout reliability, and coverage across complex regulatory environments. Those are verifiable claims buyers can test, not just narrative positioning.
If your advantage can’t be demonstrated or independently validated, it tends to collapse under scrutiny.
3. Would naming a competitor expand or shrink your perceived market?
In some cases, referencing a competitor helps buyers place you quickly. It reduces explanation cost and signals where you sit in the landscape.
In other cases, it can unintentionally anchor you to a narrower interpretation of the category or an adjacent use case.
So the real question is: does the comparison help buyers understand your space faster, or does it compress how they see your potential?
The answer depends on how mature the category is and how differentiated your use case is.
4. Has a competitor already done the work of educating the market?
Category education is expensive and slow. When someone else has already invested in explaining the problem, you often inherit a more informed and higher-intent audience.
That’s an advantage when it exists.
When it doesn’t, you need more time, more repetition, and usually more capital before traction becomes efficient.
The deciding factor is whether you have the runway and focus to carry both education and conversion at the same time.
What this ultimately comes down to
Deel and Remote built the room. RemotePass operated inside a furnished corner of it, competing in a category that was already defined. Stears looked at existing rooms and decided none fit its audience, then built a new one entirely.
Both were correct. Both were disciplined reads of market structure, not emotional reactions to competitors.
That is the discipline this framework is asking for: before the next launch, before the next homepage rewrite, before the next positioning debate – know whether you are competing inside an existing mental space or carving a new one.
Everything else follows from that clarity.
