Should startups target buyers who already recognize the problem, or educate buyers and create the market?

Chris Degnan · Nov 10, 2023

The right early ICP was digital-native customers already in the cloud who had pain with Redshift, rather than customers who had to be convinced to move to the cloud at all

Amazon Redshift signed a thousand customers in nine months and created the market despite being a weak product, and the cloud vendors themselves were already doing the work of convincing companies to move to the cloud

Scope: about Snowflake's early days from 2013

11:15 20Sales: Five Lessons Scaling Snowflake to $1BN ARR, Why Customer Success is BS and Should Be Removed, Why All Sales Reps Should Do Eight Calls Per Week & Why You Should Hire a Head of Sales Sooner Than You Think with Chris Degnan, CRO @ Snowflake

Harry Stebbings · Nov 10, 2023 · hedged

If you have to educate the customer that they have a problem, the deal is too hard; they must already know they need it and be in market

Scope: Harry raises that this may sacrifice category creation

12:56 20Sales: Five Lessons Scaling Snowflake to $1BN ARR, Why Customer Success is BS and Should Be Removed, Why All Sales Reps Should Do Eight Calls Per Week & Why You Should Hire a Head of Sales Sooner Than You Think with Chris Degnan, CRO @ Snowflake

Chris Degnan · Nov 10, 2023

Selling into a large existing market where buyers already know they have the problem is far better than educating them, because convincing people they have a problem creates eighteen-to-twenty-four-month sales cycles

Customers already bought expensive data warehousing, so the pain and budget existed and the sales cycle was short

Scope: from a sales perspective

13:10 20Sales: Five Lessons Scaling Snowflake to $1BN ARR, Why Customer Success is BS and Should Be Removed, Why All Sales Reps Should Do Eight Calls Per Week & Why You Should Hire a Head of Sales Sooner Than You Think with Chris Degnan, CRO @ Snowflake

Matt Plank · Dec 20, 2024

It is much easier to sell a product that replaces an existing budget line than one that creates a new category

With a replacement you know a deal exists and just need to beat competitors; creating budget for something that doesn't exist means prospects can end an evaluation by choosing to keep doing it on paper

Scope: based on his own experience at EchoSign vs Rippling

7:38 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank

Harry Stebbings · Mar 7, 2025

If you have to educate a customer that the category itself matters, don't bother — the sale will be too hard

It's like fundraising: persuading a VC to believe in the category itself is a losing effort; competing on options within an accepted category is fine

29:53 20Sales: Everything You Know About Sales Playbooks is Wrong | How to Hire and Train Your First Sales Hires | How to Crush Pipeline and Deal Reviews as a Team | How to Structure Sales Teams and Sales Comp Plans with Julian Teixeira, CRO @ 1Password

Julian Teixeira · Mar 7, 2025

With buyers who don't care about your problem, the job is to tap into priorities they already hold rather than create a new set of priorities for them

Security practitioners juggle many priorities, so you contextualize what not solving the problem costs them and connect it to what they already care about, like keeping employees safe

31:31 20Sales: Everything You Know About Sales Playbooks is Wrong | How to Hire and Train Your First Sales Hires | How to Crush Pipeline and Deal Reviews as a Team | How to Structure Sales Teams and Sales Comp Plans with Julian Teixeira, CRO @ 1Password

Harry Stebbings · Aug 4, 2025

You don't want to have to educate customers on the problem, because that makes selling a two-step convince rather than one

With LPs he'd have to convince them venture is worth investing in and then that he is the right manager — two steps instead of one

Scope: stated as his own approach to fundraising, offered as an analogy

26:21 20Sales: $0-$3.7BN: The Databricks CRO's Playbook to Build the Fastest GTM Engine in SaaS History | How Databricks Beat Snowflake | How To Build a Sales Org of 5,000 and Close $190M Deals with Ron Gabrisko

Sean Murray · Jan 24, 2024

The best sellers are adapting by revisiting their ICP and target accounts, adjusting messaging, and teaching buyers about non-obvious problems rather than the obvious one

Average sellers pitch against 'the monster under the bed' the buyer already knows about; better sellers reveal the hidden problem the buyer isn't thinking about

13:08 20Sales: How to Scale Into Enterprise Effectively and the Biggest Mistakes Made When Making the Move From PLG to Enterprise, Why Discovery Today is F***** & The Biggest Lessons on How to Do Sales Team Compensation with Sean Murray, CRO @ Greenhouse

Imran Khan · Aug 26, 2024

A company must actively educate the market about how its product works, because if you don't tell your story someone else will and misinformation fills the gap

Most advertisers didn't understand how Snap worked — they only saw their children using it — so a sales team had to go educate the world

52:39 20VC: Why the IPO Market is not Closed | Why Revenue Multiples are BS and Founders Need to Change | Advice From Jack Ma, Jamie Dimon and Evan Spiegel | Lessons from Taking Snap & Alibaba Public with Imran Khan

Julian Teixeira · Mar 7, 2025

Sellers should anchor to the problem rather than the product; if the buyer doesn't recognize the problem you have an uphill battle, but educating them on the problem is the job

Once the buyer clearly understands the problem they lean in, and the product then just serves as proof the solution is real; nobody disputes that weak or reused credentials are a problem, the debate is only about how to solve it

Scope: agrees the battle is uphill if the buyer rejects the problem

30:18 20Sales: Everything You Know About Sales Playbooks is Wrong | How to Hire and Train Your First Sales Hires | How to Crush Pipeline and Deal Reviews as a Team | How to Structure Sales Teams and Sales Comp Plans with Julian Teixeira, CRO @ 1Password

Harry Stebbings · Jan 24, 2024

Having to educate your customer makes selling much harder

Analogy to fundraising: pitching a VC who knows nothing about your space is far harder

13:59 Educating uninformed buyers significantly raises sales difficulty

Matt Swulinski · Aug 15, 2026

Products that are hard to explain need longer-form 30-second to one-minute video ads to educate the market before other placements convert

The average person doesn't understand dictation-into-any-text-box, so YouTube education video at hundreds of millions of impressions fed non-branded search, PMAX and display where people eventually converted

35:11 Long form paid video must educate the category first