How scarce is the pool of sales talent qualified for early-stage startups?

Chad Peets · Aug 23, 2024

Being an early-stage sales leader is the worst job in software, and almost no one who has taken a company from zero to scale is willing to go back and do it again

The zero-to-one grind is so punishing that operators who have completed it, like those at Snowflake, would refuse to repeat it

Scope: specific to early-stage / pre-product-market-fit sales leadership

11:25 20Sales: How Snowflake Built a Sales Machine | Why You Have to Hire a CRO Pre-Product | Why Most Sales Reps Do Not Perform | Why Hiring Panels are BS in Interviews | Why Remote Sales Reps Do Not Care About Their Development with Chad Peets

Harry Stebbings · Sep 27, 2024

You will never get a truly great second-time sales leader to build again, because they know how hard it is

Having done it once, they won't go into another company at $1M ARR and go through it again

49:24 20Sales: Scaling Hubspot from $3M to $1BN in ARR | How to Hire and Ramp Sales Teams | How to Scale Customer Success Successfully | How and When to Go International and Crush It with Jeetu Mahtani

Harry Stebbings · Nov 22, 2024

You will never get a great sales leader willing to take a company from near-zero twice, because the early days are so hard — you only get that from someone at the start of their career who lacks options

The early-stage job is brutally hard and once someone has taken a company to $100M they won't go back

34:16 20Sales: What I Learned Scaling Datadog from $60M to $1BN in ARR | How to do Outbound in 2024 | Why Discounting is Dangerous and Contract Sizes are Misleading with Dan Fougere

Matt Plank · Dec 20, 2024

You will not get the proven all-star VP of sales to join your very early company; founders should instead recruit from the tier directly beneath that person

People who have already done the zero-to-one grind won't do it again — Parker Conrad wanted Sam Blond first at Rippling, Sam declined, so Parker went one level down the tree

58:07 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

Ron Gabrisko · Aug 4, 2025

The next generation of sellers has to be taught to outwork everyone, and a culture that tolerates dialing it in won't survive on his team

Selling is going to get even more competitive

Scope: accepts some people will self-select out to startups

39:03 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

Chris Degnan · May 23, 2026

The entitlement culture among reps that COVID accelerated is now reversing, because hungry young graduates who can't find jobs will take the entitled reps' lunch

College grads are struggling to get jobs, which changes their mindset and makes them desperate to work

51:24 20Sales: The $100M CRO Bubble: Why Anthropic Are Causing a Comp Crisis | Why You Should Never Hire From Salesforce or Service Now | How to Hire, Train and Forecase in a World of AI with Chad Peets and Chris Degnan

Chad Peets · May 23, 2026

The US has become culturally soft and people have forgotten the hard work behind their achievements, though the trend has been swinging back over the last year or two

He sees the founders he works with now putting in 70-hour weeks, which was not the case a couple of years ago

Scope: An issue far broader than salespeople; Declines to comment on Europe here

51:50 20Sales: The $100M CRO Bubble: Why Anthropic Are Causing a Comp Crisis | Why You Should Never Hire From Salesforce or Service Now | How to Hire, Train and Forecase in a World of AI with Chad Peets and Chris Degnan

Chad Peets · Aug 23, 2024

Recruiting is harder today than it has ever been for reps who will put the work in and want development, and he has no solution for it

A lot of reps today simply don't care — a mindset he doesn't understand, since he goes all in on anything he does

Scope: scoped to the specific rep profile he hires for

44:16 20Sales: How Snowflake Built a Sales Machine | Why You Have to Hire a CRO Pre-Product | Why Most Sales Reps Do Not Perform | Why Hiring Panels are BS in Interviews | Why Remote Sales Reps Do Not Care About Their Development with Chad Peets

Chad Peets · Jan 9, 2026

Obsessive, high-intensity salespeople are harder to find now than ever, and especially hard to find in Europe because the culture there tolerates things like taking three weeks off while the rest of the company keeps running

European working norms conflict with the always-on expectation the rest of the company operates under

Scope: says such people can still be found, just with difficulty

10:56 20Sales: Why the Best Sales People are F**** in the Head | Why Remote Work is BS | Why Europe is a Nightmare for Recruiting Sales Teams | How to Build a Sales Machine | What Everyone Gets Wrong Today in Sales with Chad Peets

Harry Stebbings · Aug 4, 2025

Sales reps today don't want to work hard anymore — they want to dial it in and go home

38:37 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

Chris Degnan · Oct 10, 2025

Today's sales workforce has a generational entitlement problem — younger people expect big money without putting in the grind

His own background was being first in and last out; post-COVID it was hard to get people back into Snowflake offices, and a new grad wanted a job without being willing to live in any of the office locations

Scope: varies by company

25:53 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

Sam Blond · Apr 12, 2024

The pool of qualified early-stage top-performing AEs is in the thousands — far larger than founders assume.

Multiply the large number of startups that hired up to 10 sales reps over the last five years by their top two or three reps; Sam's own personal network at Brex was fertile recruiting ground with countless qualifying AEs.

19:48 20Sales: The Biggest Sales Lessons Scaling Brex to $400M ARR, Why Startups are Doing Outbound Wrong and How to Fix It & Why Demand Gen is the Bottleneck for all Startups and How to Solve it with Sam Blond, Former CRO @ Brex

Larry Shurtz · May 10, 2024 · hedged

There is an abundance of wildly talented salespeople available in the market today

The pool of highly talented people is larger and larger, so the abrasive star is replaceable

29:51 20Sales: How to Build Vertical Sales Teams, Why No Customer Success is BS and Everyone Needs it, How to Hire, Train and Retain the First Reps and Lessons Scaling to $2.1BN Revenue and 1,300 People with Larry Schurtz, CRO @ Genesys

Carlos Delatorre · Jan 24, 2025

The reputation of salespeople as slimy or greedy is the thing most worth changing about sales, because it deters capable people from a job that could be the best they've ever had.

The stigma prevents capable people from pursuing sales careers.

64:16 20Sales: Why Every Sales Rep Should Do Pipeline Generation & How to Teach Them | Verticalised Sales Playbooks: When and How | How the Best Sales Reps and Leaders Structure Their Time with Carlos Delatorre, CRO @ Harness

Becca Lindquist · May 2, 2026

The perception of sales should change from indiscriminate cold-call volume to critical thinking about a customer's business, which would make more people willing to become sellers

People like product leaders avoid sales because of how it feels, not because of what good selling actually is; she concedes plenty of sellers do fit the bad stereotype

Scope: acknowledges many salespeople do behave the stereotyped way

64:11 20VC: Inside Clay's Sales Playbook Scaling to $100M ARR | How to Set Sales Comp Plans | How to Read Sales Talent Linkedin Profiles | What Profiles to Hire & Fire | How to Increase Performance and Speed in Sales Teams with Becca Lindquist

Carlos Delatorre · Jan 24, 2025

Fewer than 10% of sales reps are actually good at pipeline generation; the ability and tenacity for it is highly correlated with elite salespeople

It's hard work requiring tenacity and willingness

24:58 Pipeline generation ability is the scarce trait

Kyle Norton · May 30, 2025 · hedged

Even if there is some truth to young people being less work-driven, there are still plenty of candidates with the grit and tenacity to build a world-class team

He has not personally encountered the problem in his own hiring

54:43 Plenty of gritty candidates exist despite generational work ethic concerns

Dan Fougere · Nov 22, 2024

A proven, legitimate CRO will not join a pre-revenue company; if you are good enough to join a company at $60M ARR growing 100% year over year, there is no reason to take a zero-revenue company

Once you are a legit CRO candidate you have better options — he went to Datadog at $60M ARR doubling; Carlos went to MongoDB; early-stage companies get leaders earlier in their careers who are more like first- or second-line leaders

33:15 Proven cros have better options than pre revenue

Dan Fougere · Nov 22, 2024

He would take a job at a smaller-revenue company again, but would not do the build-from-scratch CRO job again — only because he no longer has to; sales leaders who haven't had the big financial outcome keep doing it

He left Medallia at ~$300M for Datadog at ~$60M and it worked out, so revenue size isn't the objection; the objection is that building enterprise sales, messaging and forecasting from nothing is chewing glass, and there's no reason to chew glass if you don't have to

34:38 Financial outcome not company size drives refusal

Kim Graves · Jun 27, 2025

Enterprise sales is the hardest role to hire for in sales today, especially at a scale-up, because you need someone who has closed big deals but is also scrappy enough to build from scratch

The combination of big-deal experience and willingness to be resourceful and build from nothing is rare

71:54 Enterprise sales leaders are hardest to hire needing both big deal experience and scrappy builder instincts

Harry Stebbings · Mar 7, 2025

The majority of salespeople are not very good, and the majority of sales leaders are not very good.

He interviews them and, from doing the shows he's done, believes he is a better sales leader than most sales leaders he has met

14:10 Most sellers and sales leaders are simply not good

Sam Lessin · Aug 11, 2023

Early-stage sales hiring is structurally almost impossible because good salespeople are anti-correlated with wanting to join early

Sales is coin-operated — the good ones go where the playbook is clear so they can make bank; the people who want an entrepreneurial adventure early are almost always the worst salespeople; he has never successfully hired sales himself

40:15 Good salespeople are anti correlated with wanting to join early stage startups

Harry Stebbings · Jan 9, 2026

There are only about three genuinely great enterprise sales leaders in Europe

34:18 Europe has only a handful of great enterprise sales leaders