Position

position: lead guest team

Turn a fuzzy product description into a defensible positioning canvas and a pitch narrative your whole team can tell the same way. Built from 138 insights from 43 Lenny's Podcast guests. Lead team: April Dunford, Andy Raskin, Arielle Jackson.

When to use

• Prospects say 'say that again', mislabel you ('you're just like X'), or say 'I can do that in a spreadsheet'
• Founder pitches brilliantly but new sales/marketing hires tell a different story
• The market shifted and you are positioned for what it used to be
• You are about to write homepage copy, name something, brief a designer or launch (positioning comes first)
• Series B-ish: founders can no longer attend every call and the story must travel
• You are debating whether to create a new category or join an existing one
• You have a deck, landing page, PRD intro or one-liner and want it graded

Step 1 — Diagnose (ask before answering)

If the user attached a deck, homepage copy, pitch script, call transcript or customer list, read it first and infer answers. Then ask at most 4:

1. B2B or consumer? Who buys (one person or a group)? B2B/group buyers route to Dunford + Raskin; consumer routes to Jackson's benefit/Bar Test and narrow-audience plays.
2. Stage: pre-launch / few customers / growth-stage with a sales team? Pre-launch gets a thesis and loose net; growth-stage gets tight best-fit and alignment work.
3. What do prospects do today instead of buying you, and who is on the shortlist? This is the input to everything; if the user cannot answer, ask sales to list it.
4. What is wrong right now? (confusing pitch / lost to no decision / team tells different stories / crowded lookalike category / need a category call). Routes the play.

Step 2 — Pick the play

If… (situation)	Use	From	Why
Any B2B product, no clear positioning	Five-step canvas: alternatives, capabilities, value themes, best-fit customer, category	April Dunford	Category last; the order is the method
Team/customers describe you in different ways	Ten-person test, then word-for-word alignment	Arielle Jackson, Claire Butler	Most weak positioning is misalignment
Complex B2B, group buyers, buyers inert ('no budget this quarter')	Strategic narrative: old game to new game	Andy Raskin	Sells a movement, not a feature comparison
Lookalike competitors keep getting compared to you	Narrative shift or force-a-choice differentiator	Raskin, Mike Maples Jr.	Stop arguing you are better; be different
Pre-launch or first handful of customers	Positioning thesis + loose fishing net	April Dunford	Thesis is partially wrong essentially always
Consumer or startup copy sounds like jargon	Bar Test + benefit-as-H1 + swappable one-liner test	Arielle Jackson, Meltem Kuran Berkowitz	Copy must be language people actually say
Considering a new category	Category readiness test (budget, words, competition, scope)	Barbra Gago	Most B2B teams should join an existing category
Efficiency/cost-saving product, weak pull	Reframe savings as growth	Jason Cohen	Buyers pay a fraction of savings, full value of growth
Enterprise buyer, premium product, no reason to pay more	Challenger insight (hidden business problem first)	Matt Dixon, Jeanne Grosser	About 80% buy to avoid pain or reduce risk

Step 3 — Run it

Play A: The five-step canvas (April Dunford)

1. Competitive alternatives. Ask sales one question: if we did not exist, what would the customer do? Write two lists: the status quo (spreadsheet, pen and paper, intern, doing nothing) and the shortlist (named vendors). B2B loses about 40% of deals to no decision, so you must beat both plus indecision. Do not start from 'why does everybody love us'; that yields untestable opinions.
2. Differentiated capabilities. List everything you have that the alternatives do not (features, pricing model, support, portfolio, integrations). If a capability is shared, it is not differentiation.
3. Value themes via so-what ladder. For each capability ask so what, why does anyone care? until you reach value others cannot deliver. Cluster into 2-3 themes. Example ladder (LevelJump): built on Salesforce, so enablement data is integrated with sales data, so you can measure ramp time and quota impact, so faster ramp means revenue sooner. If you have happy retained customers, the value already exists; you are uncovering it.
4. Best-fit customer. Ask what characteristics make a target account care a lot about that value. Express them as queryable company attributes (team size, budget, tools in use, situation), not demographic personas. Early on, find who actually loves you and pays more, not who you wish did (Camille Ricketts).
5. Market category, last. Pick the context that makes the value obvious to those buyers. Test 2-3 candidate categories against the value themes. Default: a niche play inside an existing category buyers already understand, then expand later.
6. Positioning statement. Write: We are the best in the world at [value] for [best-fit customer], unlike [alternatives], because [capabilities], in the [category] context.

Done when: a qualified prospect leans in when you tell it, and sales, product, CS and the CEO all agree. Run it as a team sport (marketing, product, sales, CS, CEO in one room; a few days in-house, up to a week with prep and follow-up).

Play B: Strategic narrative (Andy Raskin) — B2B only

1. Name the shift in two or three words (software to cloud, transactions to subscriptions, opinions to reality). It will overstate; that is fine. Never copy another company's deck and swap the logo.
2. Name the stakes. Show winners already playing the new game and losers dying. The buyer must see the future as a fork between very bad and very good, not sort of okay. Avoid overstated stats that feel disingenuous.
3. Name the object of the new game as a rallying-cry question (for example: how do you turn your experts into champions of learning?).
4. Name the obstacles that make winning hard. Your problems-you-solve become obstacles to a goal you already made life-and-death.
5. Show how you help overcome each obstacle with product and customer success stories.
6. Make this one story the north star for marketing, sales, roadmap, fundraising and recruiting. Treat it as principles, not a slide template.

Play C: From positioning to pitch (Dunford)

1. Write the insight: your point of view on the market, the problem inside the problem, phrased so the target customer nods. If you have none, reverse-engineer it: what must the buyer know to understand why your differentiated value matters?
2. Storyboard: insight with stats, how alternatives handle it (worse for this customer), your differentiated value in that context.
3. Marketing and sales turn it into deck/demo/script; test with qualified prospects. If sales cannot tell the story they will make things up.
4. Arm the champion with talking points for IT, purchasing, legal, end users and the economic buyer.

Play D: Copy tests (Arielle Jackson)

1. Define the target. Role-play two of them at a bar: I just started using [product], it's a [category] that [benefit]. Peer says tell me more; say the differentiator aloud.
2. Anything that sounds unnatural (leverages, empowers) gets rewritten. Benefit = the line a customer would repeat to a peer, ideally the homepage H1 (Square Stand: turn your iPad into a point of sale).
3. Swappable test: paste your one-liner onto a competitor site; if it still works, rewrite (Meltem Kuran Berkowitz).
4. Rank messaging by counting what about 100 survey respondents value first, second, third, in their words (Georgiana Laudi).

Play E: Category call (Barbra Gago, Todd Jackson, Zoelle Egner)

Check four factors: do buyers have a budget line, what words do they use for the pain, who competes, how big is the scope you want. If budget and vocabulary already map to an existing category, join it and position as a much better version (Ironclad and CLM; Greenhouse stayed ATS). Check how G2 or Software Advice groups you. If you truly span many labels, run dual track: sell in the existing category, educate on the umbrella (Miro, visual collaboration). Try new language fast and abandon it if buyers do not adopt it.

Where the experts disagree

1. Create a category vs join one. Camp A: Christopher Lochhead (positioning against competitors is fighting for scraps; design a category), Andy Raskin (movement over naming). Camp B: April Dunford, Todd Jackson, Barbra Gago, Zoelle Egner, Emilie Gerber (most legendary companies did not create their category; buyers shop where budget exists; press wants an incumbent frame). Use A when there is a real inflection point and nobody is shopping for what you do. Use B when buyers already have budget and words for the problem. Default: B, with Raskin's narrative as the story on top.
2. Tight vs loose early positioning. Camp A: Lulu Cheng Meservey, Ryan Hoover, Jackson (narrow audience, win about 10 diehards, expand). Camp B: April Dunford (document a thesis, keep external language loose, tighten once a pattern emerges). Use A when you already know who loves you; B when you have a handful of customers and no pattern. Default: thesis internally, loose net outside, tighten at the first shared attribute among lovers.
3. Sell vision vs sell avoided pain. Camp A: Raskin's new-game story with a rallying question. Camp B: Jeanne Grosser (about 80% buy to avoid pain or reduce risk), Matt Dixon (insight about a hidden business problem). Use A for founder-to-founder or innovator audiences; B for enterprise buyers with targets to hit. Default: frame the stakes as risk of falling behind, then the new game.
4. Positioning vs experience-first brand. David Placek argues to start from behavior and experience rather than positioning statements; April Dunford treats positioning as the input to messaging and brand. Default: positioning first for B2B; for consumer, validate with the Bar Test.

Deliverable

# Positioning Canvas: [Product]  (date, owner, workshop attendees)
## 1. Diagnosis
Symptoms observed: [confusion signals / no-decision rate / inconsistent stories]
## 2. Competitive alternatives
Status quo: [..]   Shortlist: [..]
## 3. Differentiated capabilities -> value themes (so-what ladder)
| Capability | So what | Value theme |
## 4. Best-fit customer (queryable attributes)
[company size, situation, tools, budget; who loves us and why]
## 5. Market category
Chosen: [..]  Rejected: [..] and why  Dual track? [y/n]
## 6. Positioning statement + one-liner (passes Bar Test and swappable test: y/n)
## 7. Strategic narrative
Old game -> new game: [..]  Stakes: [..]  Rallying question: [..]
Obstacles: [..]  How we help: [..]  Proof: [..]
## 8. Pitch storyboard (insight / alternatives / differentiated value / proof / champion kit)
## 9. Thesis status (pre-PMF only)
Assumptions to validate: [..]  Tighten trigger: [shared attribute among lovers]
## Next 3 actions
1. [Test the narrative with 5 qualified prospects; log lean-in vs confusion]
2. [Run the ten-person test across execs, sales, CS and customers]
3. [Schedule a positioning review in 6 months, or on market or product change]

Grade existing work

Score each 1-5 (1 / 3 / 5), total /40.

Criterion	1	3	5
Alternatives	Only lookalike vendors	Shortlist but no status quo	Status quo plus shortlist, from sales
Differentiation	Generic benefits any rival could claim	Features differ, value unclear	So-what ladder to value only you deliver
Value themes	Long feature list	5+ themes	2-3 customer-worded themes
Best-fit customer	Demographic persona	Segment with some attributes	Queryable company attributes, evidence from lovers
Category	Chosen first or invented without budget evidence	Reasonable but untested	Chosen last, makes value obvious
Language	Jargon, swappable one-liner	Clear but flat	Passes Bar Test; benefit is the H1
Narrative	Problem, solution, better than rivals	Insight present, no stakes	New game, stakes, obstacles, proof
Alignment and testing	One person's doc	Team saw it	Team agreed; sales can tell it; qualified prospects lean in

Output: score per criterion, total, then top 3 fixes, each naming its guest or framework (for example: fix 1, add the status quo to alternatives, April Dunford).

Red flags

• Starting from market category or brand values instead of alternatives (April Dunford).
• Marketing or PM cooking positioning alone, then throwing it over the wall (Dunford).
• Stopping at a positioning doc; sales cannot pitch it (Dunford).
• Pitching 'we're better' without saying better at what, for whom (Jen Abel, Dunford).
• The arrogant doctor pitch: problem, my solution, better than the other treatments (Raskin).
• Writing in a way people do not talk; internal acronyms where buyers Google plain words (Arielle Jackson, Raaz Herzberg).
• Tight external positioning before you have data on who pulls (Dunford).
• Cool technology with no so-what; refusing to position at a micro level (Dunford on Magic Leap, Segway).
• Trying to convince people committed to the opposing belief or appease everyone (Laura Modi, Lulu Cheng Meservey).
• Judging B2B positioning by whether laypeople understand the homepage rather than qualified buyers (Dunford).
• Treating positioning as done; it decays as product and market change (Dunford).

Receipts

"And so if we didn't exist in the market, what would a customer do?" — April Dunford, Lenny's Podcast (00:39:20)

"the best market category is the context I position my product in such that this value is obvious to these people." — April Dunford, Lenny's Podcast (00:24:35)

"if sales can't tell the story, they can't pitch it, if they can't pitch it, they're going to make shit up." — April Dunford, Lenny's Podcast (00:31:12)

"This is for me the definition, is that the prospect doesn't see the future as sort of okay. They see it as split between a very negative outcome and a potentially very positive outcome." — Andy Raskin, Lenny's Podcast (00:22:55)

"one of the really big pitfalls I see, especially for B2B companies, but really for everyone is they write in a way that people don't talk." — Arielle Jackson, Lenny's Podcast (00:59:28)

"And I think that's valuable because a job is an identity and people will fight for an identity. A category of software is a line item on your budget." — Zoelle Egner, Lenny's Podcast (00:55:47)

Go deeper

• references/frameworks.md — every framework in this skill, how to run it
• references/quotes.md — verified quotes with timestamps
• Related skills:
  • strategy — when positioning exposes a moat or where-to-play question
  • launch — to turn the narrative into a launch plan, story and press
  • b2b-sales — to build the founder-led pitch, ICP and pipeline on this canvas
  • price — to align packaging and willingness-to-pay with the value themes