How much of established sales wisdom still applies to building go-to-market today?

Lauren Schwartz · Oct 19, 2022

The sales skill that hasn't changed is deep curiosity — there is no substitute for it, and it is what drives relentless discovery and ruthless qualification.

Scope: frames it as an instinct/skill set rather than a tactic

42:06 20 Sales: How To Structure The Interview Process for All Sales Reps, The Must-Ask Questions When Identifying Potential Sales Talent & The 3 Biggest Mistakes Founders Make When Hiring Their First Reps with Lauren Schwartz, VP of Enterprise Sales @ Fivetran

Maggie Hott · Dec 14, 2022

Curiosity, empathy and personalization are the sales tactics that have not changed in the last five years, and every step from first outreach to demo should be personalized to the buyer

Scope: personalization includes using the prospect's name, logo and branding in the demo

56:07 20 Sales: Webflow's Maggie Hott on When to Start and How to Scale the Best Outbound Sales Team, Why Founders Should Not Hire a Head of Sales First, The Must Ask Questions When Hiring Sales Reps and How To Structure the Process

Chris Degnan · Oct 10, 2025 · hedged

Go-to-market has not fundamentally changed in the AI era — a world-class sales organization plus a world-class product still wins over shouting loudest

He believes in ethical sales, sales process and outworking the competition; the 'shout loudest' view is the arrogance of AI

Scope: concedes it might be him being old school; concedes Ali Ghodsi's loud approach has worked for Databricks

54:02 20Sales: Scaling Snowflake from $0-$3BN in ARR | Snowflake vs Databricks: My Biggest Lessons | Why Customer Success is BS and What Replaces It with Chris Chris Degnan

John McMahon · Nov 28, 2025

The art of selling has not fundamentally changed, because it is about adapting your style to different personality types (analyticals, drivers, expressives, amiables)

Selling's art dimension is about dealing with people, which requires a 'rubber band' ability to stretch to different personality types — and that human dynamic hasn't changed

Scope: distinguishes the 'art' of sales from the 'science'

4:20 20Sales: John McMahon on How to Hire, Train & Retain the Best Sales Reps | How Sales Changes in a World of AI | Sales Lessons from Snowflake and MongoDB | How to Create and Drive a Sales Process with Urgency

John McMahon · Nov 28, 2025

The regimented sales playbook still holds in an AI world: reps need both the knowledge of the playbook and the skill to execute it, with individual style varying on top of a common skill set

Like a sports team, players must know the playbook and have the skill to execute the play; knowledge can be trained but execution requires discipline and skill, and the art is the personal variation in how the same play is run

5:20 20Sales: John McMahon on How to Hire, Train & Retain the Best Sales Reps | How Sales Changes in a World of AI | Sales Lessons from Snowflake and MongoDB | How to Create and Drive a Sales Process with Urgency

Winston Weinberg · Jan 19, 2026

Far more of company building is unchanged by AI than he previously believed; the core first-principles mechanics of scaling still apply

He went two years without doing basic sales capacity planning — tying net new ARR targets to AE headcount, quota and ramp time — and these 'laws of physics' of companies hold no differently in AI

Scope: a reversal of his earlier position that company building has changed a lot

63:38 20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

Patrick Forquer · May 11, 2026

The traditional SaaS fundamentals of deep preparation, understanding the customer's business, and showing up with genuine 'positive business intent' still carry over into AI sales.

Customers can feel whether you are genuinely there to help transform their business, and doing your homework is still what earns the right to speak to long-term impact.

Scope: applies to the preparatory/discovery portion of the playbook

10:39 20VC: Inside Legora: $100M ARR in 18 Months | Jude Law Generated $50M in Sales Pipeline: The Economics Broken Down | Competing Against Harvey, the 800 Pound Gorilla | Why Legora is Undervalued at $5.5BN with Patrick Forquer, CRO @ Legora

Julian Teixeira · Mar 7, 2025

Tech sales has reverted to a much harder environment resembling sales 20-30 years ago, and many people who entered during the easy decade will drop out of the profession

For the last decade companies threw money at any real solution to a real problem; many entered sales because it needed no degree and charisma plus earning potential was enough, and that isn't what the job is now

13:23 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

Ishan Mukherjee · Apr 4, 2025

The current generation of salespeople is not prepared for how hard sales is about to become

Sales had it relatively easy the past four to five years, and winning is genuinely hard work

0:20 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox

Ishan Mukherjee · Apr 4, 2025

Over the last five to seven years salespeople have come to think selling is easy, when the only way to earn credibility is to become a consultative expert in the customer's business through real research

Twenty- and thirty-year veterans selling into automotive or airlines in Europe understand this because deep research is the only way to even get a conversation, let alone move anything

Scope: drawn from Rox's work with large legacy enterprises

24:49 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox

Ishan Mukherjee · Apr 4, 2025

The current generation of salespeople is not prepared for how hard selling is about to become

When everyone was spending freely, reps became order takers — 'shooting fish in a barrel' — so they never had to develop the harder skills

Scope: applies to founders, builders and venture too, not just sales

25:36 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox

Harry Stebbings · Apr 4, 2025

Companies didn't need outlier sales reps in the prior era because buyers were spending freely and sales cycles were compressed

Free-spending buyers and short cycles meant average reps could still close

26:25 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox

Harry Stebbings · Aug 25, 2025

The way to win in AI is to enter a space, scream the loudest, raise as much money as possible to suck the air out of the VC room, and deliver on customer promises afterwards

Capital and attention capture crowd out competitors before product delivery matters

Scope: Harvey cited as an example

31:48 20VC: Do Margins Matter in AI? | Is Defensibility Gone For Good? | Is Vertical SaaS Dead in a World of AI | What SaaS Rules Are BS and No Longer Apply in a World of AI | The Future of Venture: Why Chanel vs Walmart is BS with Byron Deeter

Harry Stebbings · Sep 22, 2025

Go-to-market has fundamentally changed in AI: you can win by entering a market, screaming the loudest, gaining mindshare and delivering from there

48:34 20VC: General Catalyst CEO Hemant Taneja on The Future of Venture Capital: Chanel vs Walmart | Lessons Scaling GC to $40BN in AUM | Investing $5BN+ Into Stripe Over 14 Rounds | Investing Hundreds of Millions into Anthropic at $60BN Valuation

Brendon Cassidy · Mar 8, 2024

Most of what we previously knew about sales has no relevance anymore to how we go to market and build sales and SDR teams; the more you can unlearn old habits and assumptions, the better off you'll be

The environment is in a state of flux — 'clay, putty' — so prior assumptions no longer hold

Scope: uncomfortable for most people

6:12 20Sales: Outbound Sales is Dead Today, Why Demand Generation Will Move Back Under Marketing, "Wisdom" that Everyone Needs to Unlearn About Sales & Why You Should Never Hire Someone You Do Not Know in Your First Five Hires with Brendon Cassidy

Raaz Herzberg · Dec 12, 2025

The under-appreciated driver of Wiz's success is an ingrained willingness to do things untraditionally rather than the way they're always done

From outside Wiz looks like a by-the-book golden company, but internally decisions like Assaf resisting pressure to hire an experienced CMO and instead giving marketing to a first-timer have repeatedly changed outcomes; the founders trust their instincts

Scope: they also make a gazillion mistakes along the way

56:09 20Growth: How Wiz Built a $30BN Brand in Enterprise | What Worked vs What Was a Mega Failure: Lessons Learned | Why Marketers Make the Worst CMOs & What To Look for in Growth with Raaz Herzberg

Hemant Taneja · Sep 22, 2025

AI's fast early adoption is not explained by loudest-voice marketing but by the fact that for the first time every CEO in every industry and country is actively asking what to do with the technology

Cloud, PCs and the internet never produced that universal pull, so early AI companies found resonance without having to evangelize

48:55 Universal executive pull not loud marketing explains fast ai adoption

Christian Lanng · Sep 27, 2023

The canonical SaaS playbook — target metrics, margins, rule of 40 — did not exist 15 years ago and was invented by founders experimenting; it should not be treated as received truth

His generation of founders was making it up as they went along, nobody knew what good SaaS metrics were; today it's treated as a machine with fixed numbers to hit

14:53 The saas playbook was improvised not discovered