Andy Raskin
Strategic narrative advisor to CEOs (clients include Gong, Dropbox, Uber, Salesforce, Square, IBM)
Where to hear and read about Andy Raskin1 episode or test
Andy Raskin is a strategic narrative advisor who helps CEOs (clients include Gong, Dropbox, Uber, Salesforce, Square and IBM) tell one story about a shift from an old game to a new game. The lesson most worth taking: pitch a change in the world that makes the buyer the hero, not a product that beats rivals.
this structure really is about defining a movement and that's very different from hey I'm going to solve your problem
The power of strategic narrative | Andy Raskin
Andy Raskin: the story and the lessons
1How Andy Raskin found the structure of a business story
A failed investor pitch sent Raskin to screenwriting books. In 1998, as a computer science major, he coded a Windows app prototype with a friend and wrote the investor pitch himself. One VC scored it a 1 out of 10 and wrote "worst" in parentheses.
The same VC wrote "not a compelling story" lower down on the mailed hard copy. A Barnes and Noble window sign about telling a compelling story pointed him to the screenwriting shelf.
Restructuring the pitch like a movie won investor interest. A term sheet arrived a few months after the rewritten pitch went out. The product did not change; only the way the company was talked about did.
His view is that a movie is a pitch for a worldview: Star Wars pitches being good and trusting the Force. He then held back 10 to 15 years from consulting on this, sure no CEO would budget a line item for story.
One post on Zuora's sales pitch proved CEOs would pay for story work. The post drew about two million views and inquiries from teams worldwide, which convinced him CEOs would budget for this.
He says it was not really about a sales deck. It was about the story the CEO tells everywhere, which then shapes the deck.
2How Raskin built his career by writing online
Raskin wrote steadily for years before anything broke out. The Zuora post was roughly his 30th or 40th piece. A teardown of Elon Musk's Powerwall pitch got a few hundred thousand views, and the next piece got a "paltry number".
He had written on Medium for a couple of years first. He describes a long stretch where "you're writing and it feels like you're talking to nobody and then sort of gradually it grows".
Open platforms let him reach readers without an editor. Medium and LinkedIn appeared around 2013 and 2014, when he started writing. He says his current work would not exist without them.
He had a small career as a freelance journalist and loved pitching articles, but even a great editor is an intermediary.
3Raskin's five-step strategic narrative
Raskin rejects the arrogant doctor pitch. The business-school pitch states a pain, offers a treatment and argues it beats other treatments. He says it sets you up to brag and invites feature comparison.
Salesforce pitching this way would have compared setup speed and features against Siebel, the giant of the space, instead of leading with the cloud.
He opens with a shift from an old game to a new game. Benioff said software was over and a new world called the cloud had new rules, and told buyers to go buy Siebel if they wanted the old game.
The pitch ends in a choice: are you in or not. The buyer, not the company, becomes the hero who must pick a side.
Step one: name the old game in a few words. Good names are short: software to cloud, transactions to subscriptions, opinions to reality. A bullet list of how the world is changing does not stick.
Short names give up completeness and overstate the case, but nobody objects. Teams that copy the Zuora deck and swap in their logo fail.
Step two: make the stakes real with winners already in the new game. Zuora's 2015 deck pointed to Airbnb and Box as winners on subscriptions and added a chart of shrinking Fortune 500 lifespans. Raskin calls that statistic "a little disingenuous" but says it makes the case.
Like Luke, who only joins Obi-Wan after his aunt and uncle are killed, the buyer must see a very bad or a very good future, not an okay one. Teams ask if they must kill the prospect's aunt and uncle, and he says yes, figuratively.
Step three: state the object of the new game as a rallying cry. Zuora's was "turn customers into subscribers"; Airbnb's was "belong anywhere", later "live there". It often doubles as the company mission.
He now phrases it as a question, such as "What would it take to turn every customer into a subscriber?", so the buyer joins as a co-adventurer. He dropped the old "promised land" label because it got too grand for a website.
Step four: recast your solved problems as obstacles. Zuora's obstacles were how to measure lifetime value with always-on customers and how to track shifting preferences. They are the usual problems, framed as barriers to a goal the buyer already cares about.
If Luke could simply destroy the Death Star there would be no movie. Because the goal is framed as life and death, ordinary problems take on emotional meaning.
Step five: the product arrives last, as the hero's magic gift. Only at this step does the pitch turn to the product, success stories and the rest of the material.
The gifts serve the hero's win, not the other way round. Raskin uses the hero's journey as background only; he found Campbell's framework too abstract and people glazed over.
4The narrative at Zuora, Gong, Drift and 360Learning
Zuora swapped owning things for the benefits of things. CEO Tien Tzuo was employee number 11 at Salesforce and learned the move from Benioff. Zuora's story was transactions giving way to the subscription economy, backed by winners already moving to it.
Pitching Ford, the story leads to a subscription for car service, which differs from a lease.
Gong moved from "our insights beat Salesforce's" to opinions versus reality. Around 2018, at about Series B, Gong's CEO wanted the narrative to multiply growth. The story shifted Gong from a sales operations tool to a tool for sales leadership.
Gong records sales calls and adds AI to surface insights. Its earlier pitch was "we record calls, and our insights beat Salesforce's".
Drift, maybe the 30th website chatbot, never argued its bot was best. It started from the world of forms, where a buyer filled in a web form and waited days, versus an always-on buyer who expects an instant reply. It called this conversational marketing.
Founders David Cancel and Dave Gerhardt framed it this way from the start, with imagery of a woman asleep with her phone.
360Learning kept "collaborative learning" and gave it a story. CEO Nick Hernandez was pitching a descriptor that fell flat. The new story: old game, a learning guru pushes courses top-down; new game, companies turn internal experts into educators.
Winners included Google's public page connecting people with its internal AI experts, and a McDonald's recruiting poster in France that Hernandez spotted. Prospects stopped asking how it differs from other learning platforms.
5What a strategic narrative does inside a company
Raskin's story becomes the bar for which features to build. Sales and customer success send constant feature requests, and teams had no way to choose. At 360Learning the test is whether a feature helps people upskill from within.
Gong's Amit Bendov told him they decline requests about recording opinions, because those belong to the old game.
Marketing content shifts from product talk to the movement. When Zuora started, roughly 80 percent of its content was trend pieces, such as how music and luxury companies embrace subscriptions.
This gives marketing near-unlimited material and feels less salesy. In Raskin's words, "your product is like a prop for making the story come true."
Raskin favors building a movement over naming a category. Other companies used "revenue intelligence" before Gong, but it became a thing because of Gong's opinions-to-reality story.
Bendov said in hindsight they could have called it "strawberry intelligence". HubSpot's inbound movement stayed constant as it went from marketing automation to CRM.
The payoff is real but hard to measure. Nobody can say if Gong grew 3x instead of 2x because of the story. CEOs report they now pitch a movement instead of features.
Raskin says pitching a movement is a better place to be than pitching product out of context.
6How Raskin runs a narrative engagement
Raskin insists the CEO lead the drafts. Looking back, the engagements where the narrative became a true north star were all CEO-led, with the CEO working on the drafts. He first accepted any sponsor, then changed.
A Zuora sales leader said the CEO's story gave him air cover while he knocked down deals on the ground. Even a product leader needs that backing so the story is not told only within product.
He builds a small team and interviews customers before drafting. The CEO forms a team of up to four, usually the leads of marketing, sales and similar functions. A kickoff fills boards with ideas, then the team interviews customers about the shift.
Customers sometimes give the team the exact words, which helps align differing internal views.
He warns that the second working session is the low point. The CEO and Raskin throw out almost every idea from the first session to make a clean first draft, and the team's reaction is painful. He says a draft is "a million times more valuable" than a pile of great ideas.
A CFO said he should have drilled home how bad it would be, so he now shows her quote on a slide to future teams. He follows Anne Lamott's "shitty first draft" idea.
Founders call him at three moments: scaling, outgrowing the story, pivoting. Around Series B, founders can no longer sit in every sales call and want their direction remembered without them. After acquisitions or new products the old story is too small, and a pivot needs a new one.
OneTrust began with data privacy, then bought other companies and needed a bigger story.
He works mainly with B2B enterprise tech and usually turns down consumer. Enterprise deals have a group buyer that needs a uniting story, and the software changes so fast that feature-by-feature comparison makes little sense.
The arrogant doctor pitch comes from an age of static products like soup cans and cars. Spec comparison still happens for something like a Fitbit.
He teaches principles and refuses to sell a template. Teams that copied Zuora's deck found it did not work. Some lay out the shift in one slide and some use none. Presentation companies offered revenue share for a template and he refused.
His closest thing is his post on the greatest sales deck he has seen.
He has teams test the story in a few sales calls first. He does not roll it out to the whole sales team at once. A good sign is buyers saying "let me tell you how that's playing out for us".
He trains salespeople to ask, "Am I crazy or are you seeing this?"
Raskin tells founders to make every slide title a takeaway. A label like "The team" becomes a claim, such as the team being veterans of the industry.
The viewer should do zero work to see the point, and the whole deck flows better.
The power of strategic narrative | Andy Raskin
A five-step story structure replaces the problem-and-solution pitch with a pitch about a shift in the world, and the CEO uses that one story across sales, marketing, product, fundraising and recruiting. Examples from Salesforce, Zuora, Gong, Drift and 360Learning show it lifting teams out of feature comparisons.
A failed investor pitch sent Raskin to screenwriting books. In 1998, as a computer science major, he coded a Windows app prototype with a friend and wrote the investor pitch himself. One VC scored it a 1 out of 10 and wrote "worst" in parentheses.
The same VC wrote "not a compelling story" lower down on the mailed hard copy. A Barnes and Noble window sign about telling a compelling story pointed him to the screenwriting shelf.
Restructuring the pitch like a movie won investor interest. A term sheet arrived a few months after the rewritten pitch went out. The product did not change; only the way the company was talked about did.
His view is that a movie is a pitch for a worldview: Star Wars pitches being good and trusting the Force. He then held back 10 to 15 years from consulting on this, sure no CEO would budget a line item for story.
One post on Zuora's sales pitch proved CEOs would pay for story work. The post drew about two million views and inquiries from teams worldwide, which convinced him CEOs would budget for this.
He says it was not really about a sales deck. It was about the story the CEO tells everywhere, which then shapes the deck.
Raskin wrote steadily for years before anything broke out. The Zuora post was roughly his 30th or 40th piece. A teardown of Elon Musk's Powerwall pitch got a few hundred thousand views, and the next piece got a "paltry number".
He had written on Medium for a couple of years first. He describes a long stretch where "you're writing and it feels like you're talking to nobody and then sort of gradually it grows".
Open platforms let him reach readers without an editor. Medium and LinkedIn appeared around 2013 and 2014, when he started writing. He says his current work would not exist without them.
He had a small career as a freelance journalist and loved pitching articles, but even a great editor is an intermediary.
Raskin rejects the arrogant doctor pitch. The business-school pitch states a pain, offers a treatment and argues it beats other treatments. He says it sets you up to brag and invites feature comparison.
Salesforce pitching this way would have compared setup speed and features against Siebel, the giant of the space, instead of leading with the cloud.
He opens with a shift from an old game to a new game. Benioff said software was over and a new world called the cloud had new rules, and told buyers to go buy Siebel if they wanted the old game.
The pitch ends in a choice: are you in or not. The buyer, not the company, becomes the hero who must pick a side.
Step one: name the old game in a few words. Good names are short: software to cloud, transactions to subscriptions, opinions to reality. A bullet list of how the world is changing does not stick.
Short names give up completeness and overstate the case, but nobody objects. Teams that copy the Zuora deck and swap in their logo fail.
Step two: make the stakes real with winners already in the new game. Zuora's 2015 deck pointed to Airbnb and Box as winners on subscriptions and added a chart of shrinking Fortune 500 lifespans. Raskin calls that statistic "a little disingenuous" but says it makes the case.
Like Luke, who only joins Obi-Wan after his aunt and uncle are killed, the buyer must see a very bad or a very good future, not an okay one. Teams ask if they must kill the prospect's aunt and uncle, and he says yes, figuratively.
Step three: state the object of the new game as a rallying cry. Zuora's was "turn customers into subscribers"; Airbnb's was "belong anywhere", later "live there". It often doubles as the company mission.
He now phrases it as a question, such as "What would it take to turn every customer into a subscriber?", so the buyer joins as a co-adventurer. He dropped the old "promised land" label because it got too grand for a website.
Step four: recast your solved problems as obstacles. Zuora's obstacles were how to measure lifetime value with always-on customers and how to track shifting preferences. They are the usual problems, framed as barriers to a goal the buyer already cares about.
If Luke could simply destroy the Death Star there would be no movie. Because the goal is framed as life and death, ordinary problems take on emotional meaning.
Step five: the product arrives last, as the hero's magic gift. Only at this step does the pitch turn to the product, success stories and the rest of the material.
The gifts serve the hero's win, not the other way round. Raskin uses the hero's journey as background only; he found Campbell's framework too abstract and people glazed over.
Zuora swapped owning things for the benefits of things. CEO Tien Tzuo was employee number 11 at Salesforce and learned the move from Benioff. Zuora's story was transactions giving way to the subscription economy, backed by winners already moving to it.
Pitching Ford, the story leads to a subscription for car service, which differs from a lease.
Gong moved from "our insights beat Salesforce's" to opinions versus reality. Around 2018, at about Series B, Gong's CEO wanted the narrative to multiply growth. The story shifted Gong from a sales operations tool to a tool for sales leadership.
Gong records sales calls and adds AI to surface insights. Its earlier pitch was "we record calls, and our insights beat Salesforce's".
Drift, maybe the 30th website chatbot, never argued its bot was best. It started from the world of forms, where a buyer filled in a web form and waited days, versus an always-on buyer who expects an instant reply. It called this conversational marketing.
Founders David Cancel and Dave Gerhardt framed it this way from the start, with imagery of a woman asleep with her phone.
360Learning kept "collaborative learning" and gave it a story. CEO Nick Hernandez was pitching a descriptor that fell flat. The new story: old game, a learning guru pushes courses top-down; new game, companies turn internal experts into educators.
Winners included Google's public page connecting people with its internal AI experts, and a McDonald's recruiting poster in France that Hernandez spotted. Prospects stopped asking how it differs from other learning platforms.
Raskin's story becomes the bar for which features to build. Sales and customer success send constant feature requests, and teams had no way to choose. At 360Learning the test is whether a feature helps people upskill from within.
Gong's Amit Bendov told him they decline requests about recording opinions, because those belong to the old game.
Marketing content shifts from product talk to the movement. When Zuora started, roughly 80 percent of its content was trend pieces, such as how music and luxury companies embrace subscriptions.
This gives marketing near-unlimited material and feels less salesy. In Raskin's words, "your product is like a prop for making the story come true."
Raskin favors building a movement over naming a category. Other companies used "revenue intelligence" before Gong, but it became a thing because of Gong's opinions-to-reality story.
Bendov said in hindsight they could have called it "strawberry intelligence". HubSpot's inbound movement stayed constant as it went from marketing automation to CRM.
The payoff is real but hard to measure. Nobody can say if Gong grew 3x instead of 2x because of the story. CEOs report they now pitch a movement instead of features.
Raskin says pitching a movement is a better place to be than pitching product out of context.
Raskin insists the CEO lead the drafts. Looking back, the engagements where the narrative became a true north star were all CEO-led, with the CEO working on the drafts. He first accepted any sponsor, then changed.
A Zuora sales leader said the CEO's story gave him air cover while he knocked down deals on the ground. Even a product leader needs that backing so the story is not told only within product.
He builds a small team and interviews customers before drafting. The CEO forms a team of up to four, usually the leads of marketing, sales and similar functions. A kickoff fills boards with ideas, then the team interviews customers about the shift.
Customers sometimes give the team the exact words, which helps align differing internal views.
He warns that the second working session is the low point. The CEO and Raskin throw out almost every idea from the first session to make a clean first draft, and the team's reaction is painful. He says a draft is "a million times more valuable" than a pile of great ideas.
A CFO said he should have drilled home how bad it would be, so he now shows her quote on a slide to future teams. He follows Anne Lamott's "shitty first draft" idea.
Founders call him at three moments: scaling, outgrowing the story, pivoting. Around Series B, founders can no longer sit in every sales call and want their direction remembered without them. After acquisitions or new products the old story is too small, and a pivot needs a new one.
OneTrust began with data privacy, then bought other companies and needed a bigger story.
He works mainly with B2B enterprise tech and usually turns down consumer. Enterprise deals have a group buyer that needs a uniting story, and the software changes so fast that feature-by-feature comparison makes little sense.
The arrogant doctor pitch comes from an age of static products like soup cans and cars. Spec comparison still happens for something like a Fitbit.
He teaches principles and refuses to sell a template. Teams that copied Zuora's deck found it did not work. Some lay out the shift in one slide and some use none. Presentation companies offered revenue share for a template and he refused.
His closest thing is his post on the greatest sales deck he has seen.
He has teams test the story in a few sales calls first. He does not roll it out to the whole sales team at once. A good sign is buyers saying "let me tell you how that's playing out for us".
He trains salespeople to ask, "Am I crazy or are you seeing this?"
Raskin tells founders to make every slide title a takeaway. A label like "The team" becomes a claim, such as the team being veterans of the industry.
The viewer should do zero work to see the point, and the whole deck flows better.