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Obviously Awesome: April Dunford’s Positioning Method for Products That Sell Themselves

· 13 min read
AI Playbook author

If customers cannot place your product in a mental category, they will invent the wrong one—or ignore you. April Dunford’s Obviously Awesome treats positioning as a deliberate process: start from real alternatives, isolate unique strengths, translate them into value, pick the market context that makes that value obvious, then align messaging and sales.

Source note: This article is an original practitioner synthesis of themes from April Dunford’s Obviously Awesome. It is not a reprint. Figures are educational illustrations of the positioning flow; support the original book for workshops, examples and nuance.

Obviously Awesome cover


0. Why this book still matters

Positioning workshops often devolve into tagline theatre: brainstorm adjectives, vote on “platform vs solution,” refresh the homepage hero, wonder why win rates do not move. Dunford—veteran of multiple B2B repositioning exercises—shows that positioning is context setting, not copywriting.

When positioning is wrong, every downstream function pays tax: longer sales cycles, confused product roadmaps, mis-hired sales profiles, and SEO that attracts the wrong buyers.

Three commitments organise the work:

  1. Positioning is a business strategy choice—not a marketing paragraph.
  2. Customers compare you to alternatives—including spreadsheets and status quo.
  3. Category teaches buyers how to evaluate you—choose it deliberately.

1. Part I — What is positioning?

Obviously Awesome — Part I opener

Figure: educational illustration from Part I of Obviously Awesome (Dunford).

1.1 Positioning as context

Positioning answers: What am I? For whom? Why pick me vs alternatives?

Positioning isPositioning is not
Context that makes value obviousA tagline brainstorm
A cross-functional agreementA marketing-only exercise
Grounded in real alternativesFantasy competitive maps
Input to messaging and salesA paragraph buried in a deck

Test: Can a smart stranger understand who it is for, why it wins, and against what—in under a minute?

1.2 The five (plus one) components

ComponentQuestion
Competitive alternativesWhat would they use if you vanished?
Unique attributesWhat do you have that alternatives lack?
Value (and proof)What outcomes do attributes enable?
Target market characteristicsWho cares a lot?
Market categoryWhat frame makes value obvious?
Relevant trends (optional)What macro shift adds urgency?

Positioning process staircase — Dunford

Figure: the staircase flows alternatives → attributes → value → best-fit customer → category → trends.

1.3 Positioning baggage

Teams carry positioning baggage: old taglines, founder stories, analyst labels, legacy categories. Dunford insists you must let go of baggage that conflicts with customer reality—or you will decorate a broken frame.


2. Part II — The 10-step positioning process

Dunford’s full process includes team and vocabulary steps practitioners often skip at their peril.

Step 1 — Understand the customers who love your product

Start with happy customers, not aspirational personas. Who already gets it? Interview them before debating category.

AskWhy
Why did you buy?Real value, not assumed
What did you compare us to?True alternatives
What almost stopped you?Objections to address

Step 2 — Form a positioning team

Cross-functional: product, marketing, sales, founder/GM. Positioning fails when marketing writes it alone and sales ignores it.

Step 3 — Align positioning vocabulary and let go of baggage

Agree terms: alternative vs competitor, attribute vs feature, category vs vertical. Kill sacred cows that contradict customer interviews.

Step 4 — List your true competitive alternatives

Ask: If we didn’t exist, what would customers do?

Include:

  • Status quo / manual process
  • Spreadsheets and docs
  • Agencies and consultants
  • Hire-a-person
  • “Do nothing”
  • Internal build

Not just logo competitors on a battle card.

Step 5 — Isolate your unique attributes or features

What do you have that alternatives lack—or cannot match economically?

Attribute typeExample
TechnicalCitation-locked RAG on private corpora
DeliveryPursuit-to-value methodology with eval gates
DataProprietary benchmark for regulated CS
GTMOutcome-based pricing tied to handle time

Step 6 — Map attributes to value “themes”

Group attributes under 2–4 value themes buyers care about—not feature lists.

AttributeValue theme
Eval harness + human overrideRisk reduction
30% handle-time reduction in pilotsOperational efficiency
Audit log + policy citationsRegulatory compliance

Step 7 — Determine who cares a lot

Best-fit customer characteristics—traits of accounts where value is 10×, not 10%.

Vague ICPBest-fit characteristics
“Enterprises”Regulated mid-market, >50 agents, audited SOPs, Tier-1 volume pain
“AI teams”CISO-mandated governance, no shadow LLM policy yet

If everyone is a fit, no one is.

Step 8 — Find a market frame of reference

Choose the category that puts your strengths at the centre.

Category choiceEffect
Known categoryFaster comprehension; harder differentiation
Subsegment (big fish, small pond)Dominance in niche
New categoryHigh education cost; high reward if you win

Positioning graph 2 — Dunford

Positioning graph 3 — Dunford

Positioning metaphor — cake

Positioning metaphor — lollipop

Figures: Dunford’s visual metaphors for how context changes what customers perceive (educational illustrations from the EPUB).

Step 9 — Layer on a trend (carefully)

Trends add urgency when credible:

  • Regulatory shift (EU AI Act, model risk management)
  • Cost pressure in customer service
  • Talent shortage in niche skills

Trend-washing: Claiming “AI-first” without unique capability → commodity.

Step 10 — Capture positioning so it can be shared

One-page canvas: alternatives, attributes, value themes, best-fit, category, trends. Version it. Sales and product sign it.


3. Styles of positioning (choose deliberately)

StyleDescriptionWhen
Head-to-headWin in existing category vs leaderClear superiority on buyer criteria
Big fish, small pondOwn a subsegmentLeader ignores niche
Create new categoryTeach market a new frameStrong budget + patience
Custom hybridBorrow known category + sharp wedgeCommon in B2B AI

Rule: Category choice affects sales motion, pricing power, SEO, analyst narrative, and hiring—not just homepage copy.


4. Part III — Putting positioning into play

4.1 After positioning: what happens next

FunctionAction
ProductRoadmap prioritises attributes that deliver claimed value
MarketingMessaging hierarchy from canvas
SalesNarrative + battle cards per alternative
SuccessOnboarding matches best-fit profile
PricingAligns to value themes

4.2 Sales narrative structure

  1. Category context (teach how to think about the problem)
  2. Why alternatives fail for this buyer
  3. Unique value themes + proof
  4. Best-fit confirmation (“this is for teams like yours because…”)
  5. Next step

Pair with SPIN Selling: Problem hypotheses come from positioning; Need-payoff validates value themes.

4.3 Website and collateral

ElementSource
HeroCategory + best-fit + primary value theme
ProofStep 6 evidence
Comparison pagesStep 4 alternatives
Case studiesStep 1 lovers

5. Common traps (expanded)

TrapSymptomFix
Starting with categoryMonths debating “platform”Start Step 4
Feature dumpingBuyers lostValue themes (Step 6)
Everyone is ICPSpray and prayStep 7 exclusion
Aspirational categoryEducation burnBig fish or hybrid
Copying competitor languageSamenessAttribute → value chain
Positioning by committee fictionNo customer quotesStep 1 interviews
Quarterly repositioningSales amnesiaVersion canvas; change rarely

6. AI product example (worked)

ElementWeakStronger
Alternative“Other LLMs”Manual review + rules engines + generic chatbots
Unique attribute“We use GPT”Citation-locked answers on private policies with eval harness
Value theme“Productivity”Risk-safe efficiency in regulated Tier-1
Best fit“Enterprises”Regulated mid-market, >50 agents, audited SOPs
Category“AI platform”Agent assist for regulated customer operations
Trend“AI is hot”Supervisor scrutiny on model risk in banking

7. Consulting proposition example

Position against staff augmentation, strategy deck shops, and pure tech vendors.

ElementExample
AlternativesBig four staff aug, offshore build shop, internal COE
Unique attributesPursuit-to-value method, eval systems, industry accelerators
Value themesTime-to-production, governance-ready, measurable ROI
Best fitRegulated enterprise with board AI mandate and thin delivery bench
CategoryAI solution engineering (pursuit-to-value)

8. Half-day workshop agenda

  1. Interview synthesis review (45 min)
  2. Competitive alternatives list—include status quo (45 min)
  3. Unique attributes inventory (30 min)
  4. Attribute → value theme mapping (45 min)
  5. Best-fit customer filter—who is out (30 min)
  6. Category options scored (45 min)
  7. Optional trend layer (15 min)
  8. Draft messaging + sales openers (30 min)
  9. Roadmap implications assigned (15 min)

9. Consulting and AI pursuit translation

Pursuit artefactPositioning input
No-bid / pursueBest-fit match
Discovery guideAlternatives + problem themes
Proposal heroCategory + value theme
Demo scriptAttributes → benefits per theme
PricingValue theme anchors

Negative cases

  • Repositioning every quarter → sales cannot tell a consistent story
  • “We’re different” without attribute proof → disbelief in procurement
  • Category too broad → 18-month education cycle you cannot fund
  • Ignoring status quo alternative → lose to “do nothing”

Health check

  • Alternatives list includes status quo and internal build
  • Every claimed value traces to an attribute
  • Best-fit customer excludes someone specific
  • Category makes value obvious without a 20-minute lecture
  • Sales and product signed the same canvas version

10. Competitive alternative interview guide

Use in win/loss and customer development calls:

QuestionCaptures
What did you use before us?True alternative
What would you do if we shut down tomorrow?Status quo + build
Why did you almost not buy?Objections + frame gaps
How do you explain us to your boss?Category in customer words
What result would make this a no-brainer?Value proof threshold

Document verbatim phrases for messaging—do not marketing-sanitize.


11. Category scoring matrix

Score each candidate category 1–5:

CriterionWeightCategory ACategory B
Makes unique value obviousHigh
Buyer knows how to evaluateHigh
You can win references quicklyMedium
Education cost affordableMedium
Analyst/SEO alignmentLow
Competitive intensityMedium

Pick the frame you can win, not the frame that sounds largest.


12. Repositioning triggers

When to rerun the 10-step process:

SignalAction
Win rate drops in core segmentRevisit best-fit (Step 7)
Sales cycles lengthenCategory may be wrong (Step 8)
Product roadmap driftAttributes no longer unique (Step 5)
New alternative emerges (e.g. native AI in platform)Refresh Step 4
Merger or new product lineFull canvas

Avoid reactive repositioning after every lost deal—look for patterns.


13. Capstone — positioning canvas

Fill before any rebrand or major pursuit:

  1. Top 3 alternatives (customer words)
  2. Top 5 unique attributes
  3. 2–4 value themes + proof each
  4. Best-fit characteristics (include anti-fit)
  5. Category choice + style (head-to-head / niche / new)
  6. Trend (if any)—one sentence, factual
  7. One-sentence positioning statement
  8. Sales opener (30 seconds)

14. Step-by-step deep dive — all 10 steps

Step 1 — Customers who love you (expanded)

ActivityOutputTime box
Interview 5–10 delighted customersVerbatim quotes2 weeks
Extract “before state” strugglesProblem language
Map what they compared you toAlternatives list seed

Negative case: Interviewing only churned users first—you learn exit reasons, not positioning strength.

Step 2 — Positioning team (expanded)

RoleResponsibility
ProductAttributes truth
MarketingCategory + messaging
SalesAlternatives + objections
Founder/GMFinal category call

Step 3 — Vocabulary + baggage (expanded)

Baggage typeExampleRelease criterion
Legacy tagline“We’re a platform”Fails customer interview test
Founder vision“Change the world”No buyer comprehension
Analyst labelGartner quadrant obsessionMisaligned with wins

Step 4 — Competitive alternatives (expanded)

Alternative classInclude?
Direct vendorYes
Internal buildYes
Manual processYes
Spreadsheet + internYes
Do nothingYes

Step 5 — Unique attributes (expanded)

Attributes must be provable and differentiating vs Step 4 list—not table stakes.

Step 6 — Value themes (expanded)

ThemeProof types
EfficiencyTime/cost study
Risk reductionAudit, eval metrics
RevenuePipeline, conversion lift

Step 7 — Who cares a lot (expanded)

Define anti-fit: accounts where you will lose or deliver poorly—sales must disqualify.

Step 8 — Market frame (expanded)

See Section 3 styles; score with Section 11 matrix.

Good trend: regulatory deadline. Bad trend: “AI” with no capability link.

Step 10 — Capture + share (expanded)

Version the canvas; quarterly review; no silent drift in sales decks.


15. Messaging hierarchy from canvas

LevelContentExample
L1 CategoryFrameAgent assist for regulated CS
L2 Primary valueTheme #1Risk-safe efficiency
L3 ProofMetric30% handle-time reduction
L4 AttributesMechanismCitation-locked RAG + eval
L5 Differentiator vs alt XBattlevs generic chatbot: audit trail

16. Consulting proposition worked example

StepConsulting AI practice
AlternativesStaff aug, offshore build, strategy-only decks
AttributesPursuit-to-value, eval harness, industry accelerators
Value themesTime-to-production, governance-ready, measurable ROI
Best fitRegulated enterprise, board AI mandate, thin bench
CategoryAI solution engineering (pursuit-to-value)
TrendModel risk supervision tightening

17. AI product anti-patterns by step

StepAnti-patternSymptom
4“We compete with OpenAI”Buyer confusion
5“We use transformers”Not unique
7“All enterprises”Long cycles, losses
8“AI platform” category18-month education
9“Digital transformation wave”Trend-washing

18. Quarterly positioning review agenda

  1. Win/loss themes (30 min)
  2. Alternatives refresh (20 min)
  3. Attribute drift vs roadmap (20 min)
  4. Category still winning? (20 min)
  5. Messaging updates assigned (10 min)

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