April Dunford (author of Obviously Awesome and Sales Pitch)22 October 2023

A step-by-step guide to crafting a sales pitch that wins

6Frameworks

15Insights

Episode overview

April Dunford explains a sales-pitch structure that translates positioning into a market setup followed by differentiated value, proof, objection handling, and a clear ask. Using Help Scout and LevelJump as examples, she shows how vendors can teach overwhelmed B2B customers how to evaluate alternatives and buy confidently. She also argues that customer indecision is often a larger obstacle than the status quo, so sellers should reduce perceived risk instead of intensifying fear of missing out.

Key ideas

Structure the pitch in two parts: a brief market setup and a longer follow-through focused on differentiated value.
Build the setup from a market insight, the strengths and weaknesses of alternatives, and agreement on the characteristics of a perfect solution.
Demonstrate each differentiated value claim through the capabilities that produce it, then add proof, handle likely objections, and make a specific ask.
Treat the first substantive sales call as collaborative discovery; disqualify prospects whose worldview or needs do not fit the product.
Help buyers understand the market and purchase criteria because uncertainty often causes B2B buying processes to end without a decision.
Reduce buyer risk with smaller commitments, guarantees, services, support, and materials that help the champion win stakeholder approval.
Develop positioning and the pitch cross-functionally with product, marketing, and sales, then pilot it with a strong sales representative and qualified prospects.
Early companies can often gain traction by dominating an underserved niche and expanding into adjacent segments rather than immediately creating a new category.

Transcript available · source text is retained privately and is not published

Frameworks in this episode

Sales3 steps

Arming the Champion

Win the champion first, then pre-load them to defeat every other stakeholder's objection

Read →

Strategy4 steps

Bowling Pin Market Entry

Dominate one underserved niche, then knock over adjacent segments until you can challenge the leader

Read →

Sales4 steps

Teaching the Customer How to Buy

Beat indecision by de-risking the buyer's decision, not by piling on FOMO

Read →

Sales5 steps

The Best-Rep Pitch Pilot

Roll out a new sales pitch by piloting it with your best rep, then let sales sell sales

Read →

Sales5 steps

The Setup-and-Follow-Through Sales Pitch

Structure a sales pitch as market setup then differentiated value, not a feature walk-through

Read →

Marketing4 steps

The 'So What?' Ladder to Differentiated Value

Ladder a differentiated feature up through repeated 'so what?' until you reach value rivals can't match

Read →

People & resources mentioned

Attributed to the moment in the episode. Timestamps are approximate.

People · 10

April DunfordMentionsApril Dunford was on this podcast and she has this book that she put out recently called the sales pitch
“April is the world's foremost authority on product positioning.”
▶ Watch at ~0:30approx.
Lenny RachitskyMentionstoday we've got another very special compilation episode something I've been pulling on more and more with the podcast and the newsletter
“Today, my guest is April Dunford.”
▶ Watch at ~0:30approx.
Matt DixonCoinedMatt is one of the world's foremost experts in sales known for his groundbreaking Research into what makes the best sales people different
“Matt Dixon wrote this book called The JOLT Effect.”
▶ Watch at ~26:00approx.
Bob MoestaMentionsBob is the co-creator of the job is to beone framework and worked alongside Klay Christensen for many years
“I was having this conversation with, um, Bob Mesta, you know, he's the Jobs to Be Done”
▶ Watch at ~28:30approx.
Geoffrey MooreCoinedJeffrey is the author of maybe the most influential and important book on go to market ever written crossing the chasm
“It's what Geoffrey Moore called bowling pin strategy.”
▶ Watch at ~53:00approx.
Andy RaskinMentionsA previous guest whose sales-story framework begins with a shift in the world.
“a previous guest Andy Raskin has a different framework.”
▶ Watch at ~1:10:30approx.
Al RiesCoinedCo-author of Positioning: The Battle for Your Mind.
“the book by Ries and Trout Positioning: The Battle for Your Mind.”
▶ Watch at ~1:16:30approx.
Jack TroutCoinedCo-author of Positioning: The Battle for Your Mind.
“the book by Ries and Trout Positioning: The Battle for Your Mind.”
▶ Watch at ~1:16:30approx.
Bong Joon-hoCoinedFilmmaker identified with Parasite and Snowpiercer.
“You know Bong Joon-ho this the the guy that did the movie Parasite?”
▶ Watch at ~1:17:30approx.
Arnold SchwarzeneggerCoinedAuthor of Be Useful.
“Arnold Schwarzenegger's new book is called Be Useful”
▶ Watch at ~1:29:00approx.

Resources · 29

Obviously AwesomeRecommendsbook · April Dunford
“She's the author of the best-selling book Obviously Awesome, which is my favorite book on positioning”
▶ Watch at ~0:30approx.
ComposerMentionssoftware · Cursor
“This episode is brought to you by Composer, the AI-powered trading platform now with retirement accounts.”
▶ Watch at ~1:30approx.
EppoMentionssoftware · Eppo
“This episode is brought to you by Eppo. Eppo is a next-generation AB testing platform built by Airbnb alums”
▶ Watch at ~2:30approx.
Sales PitchCoinedbook · April Dunford
“The book is called Sales Pitch: How to Craft a Story to Stand Out and Win.”
▶ Watch at ~4:30approx.
ZendeskMentionssoftware · Zendesk
“So, think Zendesk or, you know, whatever. They're in that space.”
▶ Watch at ~7:00approx.
Help ScoutUsescompany
“So, I work with these folks, Help Scout.”
▶ Watch at ~7:00approx.
G2Useswebsite · G2
“I'm on G2 Crowd and there's 24 CRMs in the top right corner.”
▶ Watch at ~20:30approx.
GartnerUsescompany
“And I'm looking at Gartner Group.”
▶ Watch at ~20:30approx.
GongUsessoftware · Gong
“they studied 2 and 1/2 million sales calls that were recorded on Gong and they studied it with AI.”
▶ Watch at ~26:30approx.
LevelJumpUsescompany
“a company I worked with a few years back, they recently been acquired by Salesforce called Level Jump.”
▶ Watch at ~41:00approx.
SalesforceMentionscompany · Salesforce
“they're the only one that's built on top of Salesforce.”
▶ Watch at ~41:30approx.
LinkedInMentionswebsite · LinkedIn
“If you're a B2B business, that place exists, and it's called LinkedIn.”
▶ Watch at ~47:00approx.
The JOLT EffectRecommendsbook · Matt Dixon and Ted McKenna
“Matt Dixon's new book called The Jolt Effect is really great”
▶ Watch at ~1:16:00approx.
Positioning: The Battle for Your MindRecommendsbook · Al Ries and Jack Trout
“The other one that I always recommend is like the original book on positioning”
▶ Watch at ~1:16:30approx.
The Challenger SaleRecommendsbook · Matthew Dixon and Brent Adamson
“His previous book The Challenger Sale and there was a companion book to that called The Challenger Customer. Those were also excellent”
▶ Watch at ~1:16:30approx.
The Challenger CustomerRecommendsbook · Brent Adamson, Matt Dixon, Pat Spenner and Nick Toman
“there was a companion book to that called The Challenger Customer. Those were also excellent and based on a deep set of research”
▶ Watch at ~1:16:30approx.
ParasiteMentionsfilm · Bong Joon-ho
“You know Bong Joon-ho this the the guy that did the movie Parasite?”
▶ Watch at ~1:17:30approx.
SnowpiercerRecommendsfilm · Bong Joon-ho
“Oh man you got to see this movie Snowpiercer.”
▶ Watch at ~1:18:00approx.
LamyRecommendscompany
“there's this company Lamy, they're based in Germany and they make the world's greatest fountain pens.”
▶ Watch at ~1:21:30approx.
Lamy AL-starRecommendsproduct · Lamy
“Lamy All-Star, that's my that's my that's my great product lately.”
▶ Watch at ~1:21:30approx.
Muji pensUsesproduct · Muji
“I use Muji pens.”
▶ Watch at ~1:22:00approx.
ParisRecommendsplace
“but I love Paris. Like I just love it.”
▶ Watch at ~1:25:30approx.
ThigaCoinedcompany
“run by these folks at Tiga. Shout out to Tiga.”
▶ Watch at ~1:26:30approx.
La Product ConferenceRecommendsevent · Thiga
“There's a great product management conference there called La Product Conference.”
▶ Watch at ~1:26:30approx.
PositioningCoinednewsletter · April Dunford
“I got a newsletter. That's also called Positioning.”
▶ Watch at ~1:28:00approx.
SubstackUseswebsite · Substack Inc.
“it's on Substack. So you can find it there.”
▶ Watch at ~1:28:00approx.
Positioning with April DunfordCoinedpodcast · April Dunford
“I got a podcast. It's called Positioning with April Dunford.”
▶ Watch at ~1:28:00approx.
Be UsefulMentionsbook · Arnold Schwarzenegger
“Arnold Schwarzenegger's new book is called Be Useful”
▶ Watch at ~1:29:00approx.
Lenny's PodcastMentionspodcast · Lenny Rachitsky
“You can find all past episodes or learn more about the show at lennyspodcast.com.”
▶ Watch at ~1:30:30approx.

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Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Myth Buster· 3

Myth Buster00:00

Most B2B Deals Die to Indecision, Not the Status Quo

The common read on lost B2B deals is that the buyer decided their old solution was good enough. April Dunford says that's mostly wrong: 40-60% of B2B purchase processes end in no decision, and when you dig into that data, the majority couldn't figure out how to choose confidently. So the buyer tells their boss 'now's not a good time' and delays, because delaying is the safe, risk-free move.

40 to 60% of B2B purchase processes end in no decision at all
The majority are NOT choosing the old solution over the new one
They simply couldn't figure out how to make a confident choice
Delaying to 'next year' is the risk-free move for the person on the hook

“40 to 60% of B2B purchase processes end in no decision.”
April Dunford · 00:00

“In fact, the majority of those is they couldn't figure out how to make a choice confidently.”
April Dunford · 00:00

#b2b sales#buyer psychology#indecision

Myth Buster26:00

FOMO Backfires on Indecisive Buyers

The instinct with a stalling customer is to lean into fear of missing out. Dunford cites Matt Dixon's The JOLT Effect, which studied 2.5 million recorded sales calls with AI: when a customer is already indecisive, adding FOMO makes them less likely to close. The extra pressure just paralyzes them further, so they put their head in the sand and do nothing.

The JOLT Effect analyzed 2.5 million Gong-recorded sales calls with AI
For indecisive customers, FOMO makes closing less likely, not more
Piling on pressure paralyzes an already-stressed buyer
Assumption that companies are highly motivated by FOMO is often false

“they they studied 2 and 1/2 million sales calls that were recorded on Gong and they studied it with AI.”
April Dunford · 26:30

“what his data showed is if a customer is indecisive, throwing FOMO into the mix makes it worse.”
April Dunford · 26:30

#sales tactics#jolt effect#fomo#myth

Myth Buster48:30

Category Creation Is Not the Only Way to Win

Dunford pushes back on the claim that creating a category is the only path to a legendary business. Google didn't create search, Facebook didn't create social. Most legendary companies did not create their category, and most category creators actually get overtaken by fast followers, MySpace, Ask Jeeves, Siebel. Even famed category creators like Qualtrics and Snowflake started as a niche in an existing category.

The vast majority of legendary businesses did not create their category
Most category creators get overtaken by fast followers (MySpace, Ask Jeeves, Siebel)
Existing categories answer 'what is this thing?' so early traction is easier
Qualtrics (survey software) and Snowflake (data warehousing) started in existing categories

“the vast majority of legendary businesses did not create the categories that they're in.”
April Dunford · 49:00

“In fact, most category creators lose the market.”
April Dunford · 50:30

#category creation#positioning#myth#startups

Hot Take· 3

Hot Take23:30

Buying Software Is Harder Than Selling It

Salespeople are trained and skilled; buyers usually have never purchased software like yours before and their job may be on the line if they choose wrong. Dunford argues the buyer's real fear is making a bad choice, and the 'buyer is 80% through their journey before they talk to sales' stat can just mean they're 80% of the way to buying nothing.

Most B2B buyers have never purchased software like yours before
Their real anxiety is 'what if I make a bad choice and look stupid?'
Being 80% through the buying journey can mean 80% toward buying nothing
You combat it by being helpful, not by talking more about yourself

“And what they're really worried about is, what if I make a bad choice here?”
April Dunford · 22:00

“But, they might be 80% of the way to saying, "Nope, I'm not buying nothing."”
April Dunford · 24:00

#buyer psychology#b2b sales#hot take

Hot Take30:00

Nobody Gets Fired for Buying the Market Leader

The lowest-risk decision besides doing nothing is to pick the market leader, because nobody gets in trouble for that safe choice. Dunford notes the classic line has moved from IBM to Microsoft to Salesforce. If you're the number two or three challenger, you have to overcome that inertia and the buyer's default tilt toward the safe pick.

Defaulting to the market leader is the safest choice after doing nothing
The 'nobody gets fired' brand has shifted: IBM to Microsoft to Salesforce
Challengers must overcome inertia toward the status quo and the leader
Ease of the safe pick is a real competitive disadvantage for challengers

“Who's going to Who's going to get me in trouble for picking Salesforce?”
April Dunford · 30:00

“the classic phrase was no one gets fired for buying Microsoft.”
Lenny Rachitsky · 30:30

#market leader#challenger brand#buyer psychology

Hot Take1:10:30

Why Starting a Pitch With a Trend Falls Flat

Asked about Andy Raskin's trend-first framework, Dunford critiques it for a sales context. It has no concept of differentiated value, which she calls a giant miss, and it assumes new is inherently good and old is bad, which is lazy since indecisive buyers actually find old safe. A trend is also visible to every competitor, so any of them could open the same way. That structure fits an investor pitch, not a sales pitch.

Trend-first pitches lack any concept of differentiated value
Assuming 'new is better' is lazy; buyers see old as safe and low-risk
A trend isn't unique to you, so competitors can open the same way
Trend-and-disruption framing fits investor pitches, not right-now sales pitches

“there's actually no concept of differentiated value in that pitch which for me is a giant miss.”
April Dunford · 1:11:00

“it's it's lazy to say buy this because it's new and new is better.”
April Dunford · 1:12:00

#sales pitch#andy raskin#trends#hot take

Explainer· 3

Explainer31:00

Arm the Champion to Handle the Buying Committee

A typical B2B deal involves five to seven people. Only the champion can make the deal happen, but everyone else can kill it. Your pitch has to win the champion first, then you arm them to handle every other group's objections, IT wants security and integrations, the boss wants ROI, so they can build internal consensus. You're not pitching value to those groups, just handling objections.

Typical B2B purchase has five to seven people involved
Only the champion moves a deal; the others can kill it a thousand ways
Win the champion first or you never get near the rest
IT cares about security and integration, not your value; that's objection handling
You already know the objections because you've done many deals

“Now, the other people can't make a deal happen, but they can kill it a thousand ways.”
April Dunford · 31:30

“what we're really trying to do is just cook the champion, get the champion”
April Dunford · 32:30

#buying committee#champion#b2b sales#objections

Explainer40:30

Find Your Differentiated Value With the 'So What?' Ladder

To surface differentiated value, list what you have that competitors don't, then keep asking 'so what?' until you reach value only you can deliver. Dunford illustrates with Level Jump, a sales enablement tool built on Salesforce: built on Salesforce, so what? Enablement data integrates with sales data, so what? You can measure whether enablement improves ramp time and revenue. That insight then becomes the pitch's opening.

List differentiated capabilities, then ask 'so what?' repeatedly
The answer to 'so what?' is your value, and rivals can't match it
Level Jump's edge: built on Salesforce, so enablement data ties to sales data
Differentiated value can be reversed into your market insight

“And then what we do is we go down that list of features, and we say, "So what?"”
April Dunford · 40:00

“the the insight is basically the context that makes your differentiated value important.”
April Dunford · 42:30

#differentiated value#positioning#level jump

Explainer53:00

The Bowling Pin Strategy for Taking a Market

Citing Geoffrey Moore, Dunford explains that the easiest way to take a huge market is to define an underserved segment the leader ignores, knock over that lead pin, then use it to reach the adjacent pins. She recounts her own early career: her company positioned as CRM for investment banks, then planned to expand to retail banking, financial services, and eventually challenge the enterprise leader Siebel, which ultimately acquired them.

Define an underserved segment the market leader doesn't care about
Knock over the lead pin, then expand to the three pins beside it
Establish a beachhead, grow, then challenge the market leader
Her firm went CRM for investment banks then outward; Siebel acquired them

“The easiest way to take over a great big market is to define a segment of the market that is underserved by the market leader.”
April Dunford · 53:30

“Lead pin is CRM for investment banks.”
April Dunford · 54:30

#bowling pin strategy#geoffrey moore#go to market#segmentation

Story· 1

Story07:00

The Help Scout Before-and-After Pitch

Dunford walks through a real client, Help Scout, to contrast a typical SaaS pitch with a positioned one. The typical pitch is a glorified product walk-through that leaves the buyer unsure how it differs from a shared inbox or help desk software. The positioned pitch first sets up how digital businesses see customer service differently, gets agreement on what a good solution needs, then demos features inside that differentiated context.

Most SaaS pitches are a product exposition: feature, feature, feature
That pitch never answers 'why pick us over the other guys?'
The positioned pitch opens with a point of view on the market, not the product
Features are then shown as the value they deliver, inside the differentiated frame

“The sales pitch was essentially a product exposition.”
April Dunford · 06:00

“Like that pitch is designed to answer the question, why pick us over the other folks?”
April Dunford · 12:00

#positioning#sales pitch#help scout#saas

Tool· 2

Tool1:15:30

April Dunford's Book Recommendations

In the lightning round, Dunford recommends Matt Dixon's The JOLT Effect for its data-driven findings that upend accepted sales wisdom, along with his earlier The Challenger Sale and The Challenger Customer. For positioning, she points to the original, Positioning: The Battle for Your Mind by Ries and Trout, which she's read dozens of times.

The JOLT Effect by Matt Dixon, packed with counterintuitive data
The Challenger Sale and The Challenger Customer still hold up a decade on
Positioning: The Battle for Your Mind by Ries and Trout is the foundational text
Her own Obviously Awesome is the how-to; Ries and Trout is the 'what is it' book

“Matt Dixon's new book called The Jolt Effect is really great”
April Dunford · 1:16:00

“the original book on positioning which is the book by Ries and Trout Positioning: The Battle for Your Mind.”
April Dunford · 1:16:30

#books#recommendations#sales#positioning

Tool1:21:00

The Lamy All-Star Fountain Pen

For a favorite recent product, Dunford picks the Lamy All-Star fountain pen. Lamy is a German maker of what she calls the world's greatest fountain pens; the All-Star is around 20 to 30 dollars, affordable enough not to hurt if you lose it. She says writing with a fountain pen takes a minute to get used to but then feels great, and you refill it with a cartridge rather than dipping in ink.

Lamy is a German maker of premium fountain pens
The All-Star is an affordable entry, roughly 20 to 30 dollars
Fountain pens take a moment to adjust to but feel far better than ballpoints
Refilled via cartridge (including a refillable option), not dipped in ink

“there's this company Lamy, they're based in Germany and they make the world's greatest fountain pens.”
April Dunford · 1:21:30

“Lamy All-Star, that's my that's my that's my great product lately.”
April Dunford · 1:21:30

#product recommendation#fountain pen#lamy

Takeaway· 3

Takeaway27:30

Teach Them How to Buy, and Take Risk Off the Table

What actually works with a paralyzed buyer is giving them the tools to decide: paint the picture of the market and teach them how to buy. Beyond that, de-risk the decision, split a big deal into smaller pieces, offer a money-back guarantee, or provide services and support that cover them if things go wrong. The buyer's secondary job is deciding without getting fired.

Teaching a customer how to buy lowers their stress
Split big deals into smaller pieces to reduce risk
Offer money-back guarantees and support to de-risk
The champion's hidden job: make a decision without getting fired

“this idea of teaching a customer how to buy is one way to take that stress down.”
April Dunford · 28:00

“this idea of being able to take risk off the table is a really serious one”
April Dunford · 28:00

#sales technique#de-risking#buyer enablement

Takeaway44:30

Calm Confidence: Be Honest About Your Competitors

Dunford's recommended sales posture is 'calm confidence', which comes from deeply understanding why the right customers should pick you and who is a good fit. That lets you be genuinely honest, give competitors credit where their approach fits better, fight hard for business you should win, and walk away from business where you're not the best fit.

Calm confidence comes from knowing exactly who you're right for
Give honest credit to competitors who fit other customers better
Act as a guide: these folks are good for this, we're good for that
Fight for your ideal business; walk away from poor-fit deals

“the posture we should have is calm confidence.”
April Dunford · 44:30

“we should be unafraid to fight for that business. But we should totally walk away from business where we're not the best fit.”
April Dunford · 46:00

#sales posture#honesty#competition#positioning

Takeaway1:04:30

Tightening the Pitch Can Double Deals in Weeks

Dunford frames sharpening positioning and the sales pitch as low-hanging fruit, especially when budgets are tight. Because most pitches are so bad, even a small improvement lifts how much survives the pipeline. She's seen companies double the deals moving from first call to opportunity, and one where she was VP marketing doubled revenue in two quarters. It can ship in as little as two weeks, typically about a month.

Positioning work itself can be done in about a week
Fastest full rollout of a new pitch: about two weeks; most take a month
Some companies doubled first-call-to-opportunity conversion
One company doubled revenue in two quarters by tightening the pitch

“new pitch out the door and people using it in 2 weeks.”
April Dunford · 1:06:30

“doubled the number of deals that they're bringing from first sales call to opportunity just by tightening up the pitch and getting that going.”
April Dunford · 1:09:30

#positioning#revenue#sales pitch#roi

Key ideas

Frameworks in this episode

Arming the Champion

Bowling Pin Market Entry

Teaching the Customer How to Buy

The Best-Rep Pitch Pilot

The Setup-and-Follow-Through Sales Pitch

The 'So What?' Ladder to Differentiated Value

People & resources mentioned

People · 10

Resources · 29

Insights & moments

⚡Myth Buster· 3

Most B2B Deals Die to Indecision, Not the Status Quo

FOMO Backfires on Indecisive Buyers

Category Creation Is Not the Only Way to Win

◆Hot Take· 3

Buying Software Is Harder Than Selling It

Nobody Gets Fired for Buying the Market Leader

Why Starting a Pitch With a Trend Falls Flat

✶Explainer· 3

Arm the Champion to Handle the Buying Committee

Find Your Differentiated Value With the 'So What?' Ladder

The Bowling Pin Strategy for Taking a Market

❝Story· 1

The Help Scout Before-and-After Pitch

✦Tool· 2

April Dunford's Book Recommendations

The Lamy All-Star Fountain Pen

▲Takeaway· 3

Teach Them How to Buy, and Take Risk Off the Table

Calm Confidence: Be Honest About Your Competitors

Tightening the Pitch Can Double Deals in Weeks

Myth Buster· 3

Hot Take· 3

Explainer· 3

Story· 1

Tool· 2

Takeaway· 3