Why companies avoid making the positioning decision
The most common positioning failure Rob Kaminski sees at Fletch is not bad positioning. It is no positioning - the state where a company has never formally made a positioning choice and accumulates narratives organically as different stakeholders push for different framings.
"The big mistake we see is companies never actually choose to position," Rob said on Youroast Ep1. "And so they end up with six different narratives. They're operating in six different market spaces with six different sets of competitors. The differentiation gets all squishy and they start summarizing and then we lose all clarity." [Youroast Ep1, 20:30]
The mechanism is predictable. Early in the company's life, different narratives reach different buyers and some of them convert. The team concludes that multiple framings work and keeps all of them. Over time, the sales deck says one thing, the homepage says another, the product UI implies a third, and the founder's LinkedIn posts suggest a fourth. Each is technically defensible. None of them is specific enough to create the market recognition that makes positioning a competitive advantage.
The choice is uncomfortable because choosing means excluding. Choosing "we are the X for Y" implies that you are not the X for Z, even if you could plausibly serve Z. That exclusion feels like lost revenue. It is actually the thing that makes the included buyer trust the claim.
Lens one: how well do you fit existing categories?
The first lens in the Fletch framework is a category diagnostic. B2B technology products can usually fit into multiple existing categories - CRM, project management, analytics, workflow automation - and the diagnostic asks how well the product fits each one and what the competitive landscape looks like inside it.
"What categories do you fit into today? This is what's really unique about B2B technology products. They often can fit into multiple buckets," Rob said on Youroast Ep1. "The first thing we're doing is sort of this test of like how well do you fit into existing categories. Because that is basically a spotlight of where existing demand exists. Where you can go and place yourself against competitors in that space." [Youroast Ep1, 18:00]
The variables Fletch evaluates inside each category: does the product fit, is there meaningful differentiation, how strong are the existing players, how fragmented or mature is the market, and is there white space? Each variable answers a different version of the question "is there room for us to win in this category positioning?"
The output of this lens is a map of category options with an honest assessment of the competitive dynamics in each. That map is the foundation for the positioning decision - not a conclusion, but the set of options the founding team is actually choosing between.
Lens two: when existing categories do not fit
The second lens activates when the product does not fit neatly into existing categories - either because it covers only part of the jobs associated with the nearest category, or because it is doing something genuinely novel that existing categories do not describe.
"Especially since we work with startups, often they're building something very new and novel. And so we run that category diagnostic to then be like, hmm, what you're doing really doesn't fit neatly into these categories, or the one that it does, like you're only covering part of the jobs that are associated to that category. And what this really means is like they're basically building towards a new category," Rob said on Youroast Ep1. [Youroast Ep1, 19:00]
New category positioning comes with a distinct set of risks that Rob names explicitly: no pre-built demand, no existing constraints that tell buyers what to expect, no recognition of the category name or what it is for. "Those end up becoming the angles," he said - meaning the risks become the content of the positioning work, not obstacles to avoid but tradeoffs to navigate deliberately.
The founding team that chooses new category positioning must be prepared to educate the market on the category before it can position the product within it. That is a longer and more expensive go-to-market path than existing category positioning, and it requires enough conviction and resources to sustain a longer timeline to recognition.
How Fletch structures the positioning choice
The Fletch workshop process does not arrive with a recommendation. It arrives with a map and lets the founding team make the choice.
"The very first conversation in our workshop process when we sit down with these founders, we've already done that prep work," Rob said on Youroast Ep1. "And so we're sort of sitting there, kind of with this map, and we go, all right. We've looked at your space, we've looked at the product capabilities and what you guys think you're really good at. You could go into this category and here's what the argument's gonna look like and here's what's gonna suck about that. And then we walk through the next one." [Youroast Ep1, 20:00]
Each option gets explicit tradeoffs - what the positioning argument looks like, what the competitive set is, what the go-to-market motion needs to be, and what is going to be hard. The goal is for the founding team to see the full map of choices so that when they make a decision, they are making a real choice with understood consequences rather than defaulting to the most comfortable framing or the one the last investor praised.
"Once you see the angles, it's not easy, but it makes it easier to make the choice," Rob said. [Youroast Ep1, 20:40]
The knowledge gap the positioning exercise reveals
One of the uncomfortable outputs of the Fletch positioning process is that it surfaces gaps in competitive knowledge that make a positioning decision premature.
"Sometimes a positioning exercise will actually surface all these gaps of your knowledge of like, I don't know if we're better. I've never actually spoken to someone in that industry," Rob said on Youroast Ep1. "And you're like, Okay, like, well, are you ready to actually make a positioning decision or are you still in that experimental learning phase? And sometimes that's a hard truth for some of the especially early stage founders." [Youroast Ep1, 22:00]
The implication is that positioning work is also a research protocol. The gaps it reveals are research tasks that need to be completed before the positioning decision is made. A founding team that discovers it has never spoken to a buyer in the category it is considering positioning toward has a research task, not a positioning task.
What this means before you brief a homepage sprint
The Fletch positioning framework is a prerequisite for a Weroast homepage sprint, not a concurrent workstream. If the founding team has not chosen a positioning strategy - if multiple narratives are still active, if the ICP is still described differently by different people, if the category decision has not been made - the sprint will surface that indecision in every design round and double the cost.
The prerequisite checklist for a sprint maps directly to the Fletch framework: one ICP, one category positioning strategy, a hero claim the team agrees on, and competitive knowledge sufficient to make honest best-for and not-best-for claims. Read website redesign prerequisites for the full checklist, and watch Youroast Ep1: Is your positioning ruining or powering your virality strategy? for Rob's workshop approach to getting there.
