obviously-awesome

Note: This skill is independent analysis and commentary, not a reproduction of the original text. It synthesizes the book's core ideas with modern startup practice, surfaces where frameworks are outdated or incomplete, and integrates perspectives from adjacent disciplines. For the full argument and context, read the original book.

Obviously Awesome

"Positioning is the act of deliberately defining how you are the best at something that a defined market cares a lot about." - April Dunford (2019)

When to Use

Investigate positioning when ANY of these is true:

Dunford does not give a strict numerical threshold - one strong sign is enough to warrant a positioning audit.

The Core Insight

You probably have a positioning problem, not a marketing problem.

When prospects don't understand your product, it's not because you haven't said it loud enough. It's because the CONTEXT they're using to evaluate you is wrong.

Joshua Bell experiment: World-class violinist played 45 min in a DC subway in 2007. 1,070 people walked past. Earned $32.17. Two days earlier: sold-out Boston Symphony Hall at $100/seat. Same person, same skill. Different context = different perceived value.

Cake → Muffin: Sometimes the same product needs a different category. Almost no physical difference between cake and muffin. Big contextual difference.

The 5+1 Components

Positioning is built from 5 components, plus 1 optional layer:

Critical: Dependency chain. Get the order wrong and the whole thing collapses.

Alternatives → Attributes → Value → Target Market → Category → (Trends)

Why traditional "For X who Y, our product is a Z that does W unlike V" template fails: assumes you already know category and competitors. For novel products, those are exactly what you're trying to figure out.

Detailed component definitions: see frameworks.md.

The 10-Step Process (High Level)

Step-by-step detail with team formation, baggage handling, value-theme clustering, segmentation: see frameworks.md.

The Circular Dependency (Why Step 1 Matters)

You can't position for your target market until you know who loves you. You can't know who loves you without selling first. You can't sell without some positioning.

Break the cycle: Cast wide early ("fishing-net analogy"). Don't position narrowly until you have signal from real users. Then narrow to best-fit.

If you don't have happy customers yet → you don't have positioning yet, you have hypotheses. Use Mom Test for problem validation FIRST. Don't position what you haven't built.

The Three Positioning Styles (Step 8 - The Core Step)

Market category is the context customers use to evaluate you. Three styles:

Style 1: Head to Head (Existing Category)

Compete in an existing category by being better at one specific dimension.

When to use: Established category exists, you have a clear advantage on something customers care about, you can be top-3. When NOT: Category leader is too entrenched, your advantage isn't category-level important.

Style 2: Big Fish, Small Pond (Subsegment)

Find a subsegment where YOUR strengths are most valuable.

When to use: A subset of customers has needs the leader doesn't address well, your strengths align, the subsegment is big enough.

This is often the best fit for startups - you can't out-spend the leader on the broad category, but you can dominate a slice.

Example: Janna Systems failing at "CRM for everyone." Repositioned as "CRM for investment banks": $2M → $70M revenue → $1.7B Siebel acquisition.

Style 3: Create a New Game (New Category)

Define a new category you can lead.

When to use: Existing categories don't fit, you can clearly explain the new category in customer terms, you have resources to educate the market (expensive). When NOT (most cases): You think your product is "unique" (everyone thinks that), no budget to educate, existing categories work "well enough."

Example: Eloqua coined "marketing automation": $12M → $96M → $870M Oracle acquisition.

Mark Organ (Eloqua founder) found that successful category creation comes from deeply understanding a narrow set of extreme early customers, not from executives brainstorming acronyms at offsites. The category emerges from observed behavior, not invented positioning.

When both a new market boundary AND new evaluation criteria are needed, consider creating a new category. With only one needed, stay within existing category structure. Treat as a heuristic.

Decision Tree

Does an existing category fit?
├─ YES → Are you the leader or can become one?
│        ├─ YES → HEAD TO HEAD
│        └─ NO → Is there a subsegment where you'd be leader?
│                ├─ YES → BIG FISH, SMALL POND ← often the answer
│                └─ NO → Reconsider product, or move to Style 3
└─ NO → Can you afford to educate the market?
         ├─ YES → CREATE NEW GAME (rare and risky)
         └─ NO → Force-fit Style 1 or 2

Failure Examples

• Bic for Her - Tried to create "pens for women." Pens are pens. Customers ridiculed. Failed.
• "Sharing economy for pets" / "Uber for cats" - Trend layered on product without share-economy mechanics. Disaster.
• Long Island Iced Tea → Long Blockchain - Renamed for crypto trend. Got delisted from Nasdaq.

Big Fish / Small Pond Illustrative Example: "Coke for Dogs"

Dunford's hypothetical: take Coke and reposition for the pet-treat subsegment ("tastes like bones"). Different competitors, different value, different category - same product. Sometimes a subsegment IS available; you just have to look creatively.

Wattpad case (often omitted): repositioned a writing-platform product after finding a subset of users using it differently. See cases.md.

Decision Trees

Do I have a positioning problem?

Are any of these true?
├─ Confused prospects (compare you to wrong things)
├─ Long sales cycles (always explaining)
├─ High churn (buyers don't get expected value)
├─ Price pressure (can't command premium)
└─ If multiple signs apply → likely positioning problem

Should I reposition?

Major trigger occurred?
├─ New competitor changes landscape
├─ Regulations change
├─ Economic climate shift
├─ New technology disrupts category
├─ Customer attitude shifts
└─ YES to any → Run the 4 weak-positioning signs check
                ├─ Multiple failing → Start at Step 4 (re-check alternatives)
                └─ All clear → Stay course

Dunford recommends "checking in" on positioning every six months OR when there's a major event - not mandatory periodic repositioning. Reposition when triggers occur, not on schedule. Adding a large competitor doesn't necessarily mean positioning should change.

Critical Caveats and Soft Heuristics

• "Big Fish / Small Pond is often the best fit for startups" - heuristic. Selection bias is severe in any consultant's dataset (clients tend to be companies that already need help, often because they're not category leaders). Don't read as a measured rule.
• Two-dimensional stretch (new boundary + new criteria → new category) - heuristic, not law. Use as guidance.
• "Check in every six months" - Dunford's actual phrasing is "checking in on your positioning every six months OR when there has been a major event." It's a check, not a mandatory reposition.
• No "2+/4 weak signs" threshold - the source doesn't quantify how many signs trigger a positioning problem. Use judgment.

Customer Sales Story (After Positioning Locked)

Once positioning is locked, build a sales story in 6 stages:

Sales story comes BEFORE messaging. Story drives messaging, not vice versa. Then write a master messaging document to prevent message creep.

Customers vs investors warning: Don't say "disruption" to customers. Investor language alienates buyers. Save category-creation language for fundraising.

Positioning ≠ Messaging ≠ Branding

These three terms are used interchangeably and shouldn't be.

• Positioning = internal strategic document. Defines your competitive context, unique attributes, and target market. Not customer-facing. This is what this skill covers.
• Messaging = customer-facing translation of positioning. The words on your website, in your pitch deck, in your ads. Positioning makes messaging obvious; without positioning, messaging is guesswork.
• Branding = the emotional associations customers have with your company over time. Builds slowly through repeated, consistent exposure. Can't be written in a workshop.

Key Dunford point: Most teams skip positioning and jump straight to messaging. The messaging then changes weekly because there's no foundation underneath it - every new opinion reshapes the copy. Fix the positioning first; the messaging becomes obvious.

Critical Numbers

When NOT to Use This Skill

Pre-product, validating problem? → Mom Test instead. Don't position what you haven't built.
Pure consumer (TikTok-style)? → Brand and content matter more than positioning
Commodity goods? → Price is the only differentiator
Internal tools? → No customer-facing positioning needed
Genuine 10x product / strong network effects / PLG with self-explaining UX? → Positioning matters but doesn't WIN the game

Where Positioning Is Less Critical

Modern counter-examples to "positioning is foundational":

Pattern: When product is genuinely 10x better, OR strong network effects, OR product-led, positioning matters but doesn't win.

The Big Idea

"Context is everything. Without context, no one can know if your product is good, bad, or even relevant to them."

Positioning isn't marketing, branding, or messaging. It's choosing the context customers use to evaluate you.

The frame determines: who shows up as a customer, who shows up as a competitor, what "value" means, what "expensive" means, what "good" means.

Most companies let positioning happen accidentally. Dunford's contribution: positioning is a deliberate choice, not a default.

Supporting Files

• [frameworks.md](frameworks.md) - 10-step process detail (team formation, baggage, attributes/value mapping, segmentation), positioning canvas, traditional template critique
• [cases.md](cases.md) - Janna Systems, Eloqua, Wave, Arm & Hammer, Wattpad, Redgate, Bic for Her, Long Blockchain
• [examples.md](examples.md) - Worked positioning canvases, sales-story templates, value-theme clustering examples, "so what?" tests
• [integration.md](integration.md) - Integration and conflicts with Mom Test, Crossing the Chasm, Blue Ocean Strategy, Monetizing Innovation, $100M Offers, $100M Money Models, $100M Leads, SPIN Selling, Influence