What profile should a startup's early sales hires have?

Mark Goldberger · Apr 19, 2023

Success in sales comes down to four intangibles — hunger, hustle, humility and heart — and these matter more than the tangibles.

Hunger carries you through inevitable challenges, hustle means outworking others, humility keeps you improving because someone has always done more, and heart/grit is what lets you take a punch and keep fighting.

23:26 20Sales: Why You Should Never Hire a VP Sales First, How To Create Urgency in a Sales Process, How to Do Traditional Outbound 10x Better, Why Revenue Doesn't Matter with Your First Customers | Mark Goldberger, Head of Enterprise Sales @ Ramp

Mark Goldberger · Apr 19, 2023

The biggest mistake founders make hiring sales teams is trying to hire people who fit a preconceived box

It always ends up biting you

45:46 20Sales: Why You Should Never Hire a VP Sales First, How To Create Urgency in a Sales Process, How to Do Traditional Outbound 10x Better, Why Revenue Doesn't Matter with Your First Customers | Mark Goldberger, Head of Enterprise Sales @ Ramp

Kevin Egan · Jul 12, 2023

Big-logo sales hires often fail because what actually matters is intellectual range, which does not follow from having worked at Microsoft, Oracle or Google

An early sales leader has no marketing team or product resourcing to lean on, so they must personally do writing, messaging, closing and carrying voice-of-customer back to product — that breadth only narrows as the company specializes

Scope: applies to early-stage sales leadership hires

19:27 20Sales: Slack, Atlassian, Dropbox: Five of the Biggest Lessons on Starting, Scaling and Managing Sales Teams from 25 Years Leading the Best with Kevin Egan, Global Head of Enterprise Sales at Atlassian

Lori Jimenez · Aug 2, 2023

For early sales hires, more junior talent with drive, grit and scrappiness can outperform the big-logo candidate

Junior people bring creativity, navigate ambiguity, and lack a bias from previous experience that says there's only one way to do things; startups also have the chance to identify and grow new talent

Scope: especially in the early stages of a startup

11:24 20Sales: Why The Founder Has To Be The One To Create The Sales Playbook, When To Hire Your First Rep, Why Junior is Better Than Senior, How to Manage Sales Rep Compensation, How To Onboard New Sales Reps and more with Lori Jimenez, CRO @ WorkRamp

Harry Stebbings · Aug 2, 2023

The most common hiring mistake among young founders is making the logo hire out of insecurity about their own lack of experience

Founders are aware they lack the experience themselves, so they reach for the Salesforce-branded resume

Scope: about young founders

24:12 20Sales: Why The Founder Has To Be The One To Create The Sales Playbook, When To Hire Your First Rep, Why Junior is Better Than Senior, How to Manage Sales Rep Compensation, How To Onboard New Sales Reps and more with Lori Jimenez, CRO @ WorkRamp

Jeetu Mahtani · Sep 27, 2024

Sales experience is overrated and should not be the most heavily weighted factor when hiring a sales rep

Other characteristics matter more than tenure

Scope: specifically about highly tenured reps

49:07 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

Carlos Delatorre · Jan 24, 2025

Hiring should be sequenced DNA first, then skills: spend the most time on the innate attributes you can't change, then assess which required skills the candidate has and how long the missing ones take to acquire

You can't change a person's DNA; if they lack the skills, ramp time will be very long — so you need explicit negotiables and non-negotiables

Scope: there will always be a gap

7:56 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

Kyle Norton · May 30, 2025

When hiring SMB reps early in their careers, the scorecard should be weighted 70-80% toward DNA and mindset rather than sales craft or specific knowledge

He wants a track record of excellence in anything (sales, valedictorian, sports captain, first-chair tuba), plus curiosity, coachability, grit and resilience; he's confident the internal sales training program can teach the rest

Scope: applies to SMB roles and candidates early in their careers; depends on having a strong internal sales training program

11:42 20Sales: From $2M ARR to $40M ARR: The Playbook | How to Use AI To Supercharge Your Sales Team | Why Pipeline Reviews are BS | The Sales Call Script that Closes 99% of Prospects and How to Hire the Best Sales Reps with Kyle Norton, CRO @ Owner

Chad Peets · Jan 9, 2026

Deal size and domain knowledge are teachable; integrity, grit, obsession, and new-logo closing are not — so hire for the untrainable and accept longer ramp

A good sales leader and system act like a super rep and can take someone from $200K to $2M deals; the gaps you accept must be gaps you can solve for

17:07 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

Carles Reina · Feb 14, 2026

A rep's prior background is irrelevant to success; what matters is willingness to go deep, high energy with customers, and genuine care for them

They tried all kinds of backgrounds and it made no difference; depth and care are the only things that drive value

54:58 20Sales: Inside ElevenLabs $330M ARR Sales Machine | The 20x Sales Comp Plan Reps Must Hit | How to Land and Expand in a World of AI | Why Product-Market-Fit is BS, Reps Should Not Be in the Office and Outbound is King with Carles Reina

Becca Lindquist · May 2, 2026

In hiring sellers, what the speaker looks for most is 'high slope' — smarts, drive and coachability that don't show on a LinkedIn profile — though domain knowledge still matters for certain early or specialized roles

Clay has hired mostly nontraditional sellers, and she has repeatedly seen high-slope reps (e.g. a Bloomberg hire brought in as a commercial rep) take feedback, apply it in every deal, and become top-three reps worldwide after moving up-market

Scope: slope is hard to see on a LinkedIn profile; you detect it via back channels and interviews

12:45 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

Chris Degnan · May 23, 2026

Hiring salespeople for industry expertise is bad advice; you should hire the athlete rather than someone with domain-specific knowledge

70:58 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

Mark Goldberger · Apr 19, 2023

For enterprise hires, experience selling deals of that size and to organizations of that scale matters more than experience selling into the same market segment or product category.

Mid-market AEs promoted into enterprise often flame out because multithreading three or four stakeholders doesn't prepare you for a deal magnified by an order of magnitude — it's like playing 20 simultaneous games of chess.

Scope: specific to enterprise sales roles

30:04 20Sales: Why You Should Never Hire a VP Sales First, How To Create Urgency in a Sales Process, How to Do Traditional Outbound 10x Better, Why Revenue Doesn't Matter with Your First Customers | Mark Goldberger, Head of Enterprise Sales @ Ramp

Sanjit Biswas · Dec 8, 2023

When hiring salespeople, prior experience at the same deal size matters more than industry domain expertise

Transactional selling at a few K ACV is a fundamentally different motion than consultative value-based selling; a consultative seller from HR software or CRM transfers fine because the business-value conversation is similar

Scope: a little bit more focus on deal size, not absolute

26:10 20VC: $18BN Market Cap and $1BN in ARR in 8 Years; Samsara | How to Find Product Market Fit Reliably | How to Create a Multi-Product Company | The Pros and Cons of Serial Entrepreneurship with Sanjit Biswas, Founder & CEO @ Samsara

Amit Bendov · Sep 12, 2025

When hiring sellers, matching your ACV/deal size matters more than prior experience selling into your sector

Industry knowledge can be acquired fairly quickly, whereas salesmanship is extremely hard and takes a long time to build

Scope: Within a band (e.g. $15k–$50k ACV) the difference is negligible; What matters is the category: enterprise/high-value versus high-velocity transactional selling

16:37 20VC: Why AI SDRs are BS and Do Not Work | How to Use AI in Your Sales Team and Process to Win Today | What Skills Do All New Reps Need to Have in an AI First World with Amit Bendov, CEO @ Gong

Chad Peets · Jan 9, 2026

Some AI companies are closing unusually large deals ($5-20M) at a much earlier company stage than has historically been possible, which forces a rethink of how much big-deal experience to require when hiring reps

Deals of that size carry a level of complexity he has to be cognizant of when selecting salespeople for these companies

Scope: applies to AI companies like xAI and Parloa; framed as a caveat to his otherwise unchanged view on talent

23:14 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

Shaunt Voskanian · Mar 21, 2026

Forced to choose, hire the rep who has closed deals of that size over the rep with industry/problem-area experience

Industry and landscape knowledge can be taught relatively quickly to smart, curious people, whereas the confidence and skill to run multi-stakeholder, long-cycle, EV-level deals takes a long time to build

Scope: assumes the big deal wasn't a bluebird but genuinely multi-stakeholder and champion-built; still need to test for curiosity and willingness to learn

26:47 20Sales: Inside Figma's $1BN ARR Revenue Machine | Why We Do Not Have Customer Success or SDRs | Why I Do Not Believe in Sales Quotas with Shaunt Voskanian, CRO @ Figma

Harry Stebbings · May 2, 2026

Domain knowledge can be taught but experience selling at a given contract size cannot, so enterprise deal-size experience matters more than sector expertise

It's much harder to teach the knowledge of large contract sizes than the domain

12:27 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

Patrick Forquer · May 11, 2026

For Legora it is better to hire salespeople with experience closing deals of this size than people with legal tech or law firm selling experience

Legal tech was historically more niche with much smaller ACVs, so those reps aren't used to sending million-dollar proposals; org dynamics, change management and confidence with large proposals matter more than domain familiarity

Scope: some legal tech hires have done really well

40:44 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

Maggie Hott · Dec 14, 2022

The right first sales hire is an AE with proven success at a hypergrowth company who has actually built a sales function from the ground up or watched it closely

Persona, ICP and product knowledge can be taught, but hustle, grit and knowing what ground-up building looks like cannot; someone from a great but mature company like Salesforce who joined late never built the playbooks

Scope: having sold this persona or deal size is a bonus, not a requirement

32:52 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

Brendon Cassidy · Mar 8, 2024

He will not hire a rep from a large incumbent like Salesforce, Oracle or Adobe into a startup, because there is no comparable selling motion

At a Fortune 1000 tech company everyone knows who you are and has budget; at a startup you must first convince the buyer the problem even exists, and big-company reps have never had to make that case

Scope: stated as a general rule

19:49 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

Sam Blond · Apr 12, 2024

Founders over-index on domain experience when hiring early sales reps; what matters for the first AEs is having worked in an early-stage startup environment

Scope: applies to first and second AE hires

0:00 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

Sam Blond · Apr 12, 2024

Founders over-index on domain expertise when hiring sales reps; trading off track record or early-stage experience to get domain familiarity is the wrong trade-off.

Exceptional early-stage reps with a track record are already very hard to find, so any domain requirement definitionally forces a sacrifice elsewhere — and effective people pick the domain up quickly, as Sam himself did across e-signature, HR/health insurance, and fintech.

16:05 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

Chad Peets · Aug 23, 2024

The hiring profile varies only slightly by geography, client type or ACV; what matters far more is whether the candidate's prior job was genuinely the same job

A rep selling a new product into Oracle's installed base with discount-driven wrap-and-rolls is doing a completely different job from a Snowflake rep asked to convince 25 accounts to move data on-prem to an unknown company

33:59 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

Carlos Delatorre · Jan 24, 2025

You test rep skills by interrogating history: experience at a challenger company, self-sourced pipeline generation, comparable product complexity, account size, deal price, number of stakeholders/personas, and same general domain

Operating without a big logo that sells for you is much harder; comparable price implies multiple stakeholders, a business case and more customer politics

Scope: some criteria negotiable, some not; more gaps simply means longer ramp time

9:38 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

Chad Peets · May 23, 2026

Reps from Salesforce and ServiceNow are poor hires for startups because their employers' monopoly positions mean they've never opened new logos or done real pipeline generation

When nearly everyone is already a customer, reps expand existing accounts rather than generating pipeline — a rep may claim to have 'closed Wells Fargo' when it has been a customer for ten years

7:18 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

Lauren Schwartz · Oct 19, 2022

At the earliest stage a founder should not hire a tenured head of sales, but a rep willing to kick down doors and ask hard questions that feed back into product and messaging

Early on you need market information, not someone whose career has been scaling organizations and building process

Scope: very early stage companies

16:31 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

Chris Degnan · Nov 10, 2023

The ideal first sales hire is someone with something to prove who will roll up their sleeves to do eight sales calls a week and prospect themselves

He treated the job as one he could not fail at and hit every metric because he was a little desperate; an established leader ten years in would not do that work

Scope: depends on the individual person

15:22 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

Chad Peets · Aug 23, 2024

The right response to a shrinking talent pool is to refuse to budge on the profile — willingness to put the work in is non-negotiable

44:38 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

Julian Teixeira · Mar 7, 2025

The first sales hire should be a low-ego, patient, curious person with something to prove, not the tenured rep with a fancy logo-studded resume.

You need someone who focuses on what's possible rather than blaming the absence of systems or budget, and who is motivated to build something bigger than they've been part of.

Scope: applies very early in the journey

8:08 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

Chad Peets · May 23, 2026

Large companies breed a take-more-give-less mentality, and leaders must deliberately select for people who feel privileged to be there and want to add maximum value

He saw this mentality everywhere when he returned to Snowflake; he holds himself to leaving if he isn't adding as much value as he can

56:50 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

Mark Goldberger · Apr 19, 2023

You should never bring in a VP of Sales before you have an individual seller who has figured out how to sell

A VP arrives with a preconceived playbook, processes and tooling that may not mesh with the product or the people, and forcing that square peg into a round hole creates thrash and wasted cycles at an early startup

Scope: early-stage startups

7:45 20Sales: Why You Should Never Hire a VP Sales First, How To Create Urgency in a Sales Process, How to Do Traditional Outbound 10x Better, Why Revenue Doesn't Matter with Your First Customers | Mark Goldberger, Head of Enterprise Sales @ Ramp

Rich Liu · Jun 7, 2023

The first sales hire should be a player or player-coach who sells alongside the founder and feeds learnings back, not a manager hired for the title

The message, ICP and product-market fit are still being refined, so the hire must be close enough to the founder to iterate on the story while adding selling capacity

Scope: titles are irrelevant at this stage

17:06 20Sales: PLG and Early Adopter Sales are Gone, How to do Sales Forecasting in 2023, Why You Cannot Do PLG and Enterprise from Day 1 at the Same Time and Which is Easier to Start, How to Onboard, Manage and Scale Reps with Rich Liu, CRO @ Everlaw

Rich Liu · Jun 7, 2023

Moving too fast means hiring a large-scale sales leader who romanticizes startups but can only operate by hiring others beneath them

It's a telltale sign they've been too far from the work for too long and won't or can't build a sales plan or comp plan from scratch in Google Docs without an FP&A team

18:40 20Sales: PLG and Early Adopter Sales are Gone, How to do Sales Forecasting in 2023, Why You Cannot Do PLG and Enterprise from Day 1 at the Same Time and Which is Easier to Start, How to Onboard, Manage and Scale Reps with Rich Liu, CRO @ Everlaw

Brendon Cassidy · Mar 8, 2024

You should not hire a VP of sales as your first sales hire

Founders should be actively involved in early sales themselves; the best SaaS companies have founders active in early go-to-market

Scope: assumes the founder is engaged in early sales; if they can't or won't, the underlying assumptions need revisiting

14:34 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

Sam Blond · Apr 12, 2024

Startups should sequence sales hiring by first hiring exactly two individual-contributor account executives, then running parallel paths of more ICs and a first sales leader, and only adding SDRs once a sales leader is in place

Two successful ICs qualify you to attract a great sales leader; leader searches take four to six months so you can't stall the business meanwhile; SDRs need hands-on management a founder can't provide

Scope: hire ICs two at a time, never one

12:21 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

Kim Graves · Jun 27, 2025

The best sellers are not extroverts who are great at pitching and messaging; they are consultative, curious, and ask the best questions

Scope: this is a belief she has changed

48:49 20Sales: How to Layer Enterprise Sales on PLG | How to Sell AI Tools To Enterprises That Are Scared | Should Reps Own Their Own Pipeline | Mistakes All Founders Make When Moving From Founder-Led to Rep-Led Sales with Kim Graves

John McMahon · Nov 28, 2025

Listening is the single hardest unnatural skill in sales, and most sales reps are terrible at it.

23:59 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 best enterprise salespeople sell at the very top of organizations and win through fearlessness, deep listening, and total personal security rather than through aggression

Carlo Carpinelli called on Piero Ferrari and the CEO of Ducati while everyone else called low in the org; when attacked he responded with genuine confusion and 'but why?', which disarmed people and forced them to explain themselves, putting him back in control

Scope: drawn from his experience with one rep at PTC selling mechanical CAD software

26:19 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

Great sellers are defined by listening, patience, security in themselves, and the ability to get to the bottom of the real issue quickly

Cedric Pesch has the same qualities as Carlo because he was trained under him — he moved to Italy without speaking the language specifically to learn from the best sales leader in Europe

27:35 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

Chad Peets · Jan 9, 2026

When hiring salespeople, the only thing that matters is the quality of the sales organizations they were trained in — not domain expertise or stage/scale experience

where a person was trained determines whether they learned a world-class go-to-market function; domain and scale filters are noise

58:04 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

Chad Peets · May 23, 2026

Domain or industry background is the wrong hiring filter; what matters is the quality of the sales organization the candidate was trained in and who trained them

There are great companies with terrible sales organizations and terrible companies with world-class ones, so the training methodology and DNA — verifiable through references you trust — is the real signal

Scope: applies to both regional VP and CRO hires

8:50 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

Chris Degnan · May 23, 2026

He prefers not to hire salespeople out of the security industry because security companies have historically been channel-driven organizations

Channel-driven orgs don't build direct enterprise selling skill; industry expertise matters far less than proven success selling enterprise technology

Scope: Wiz is a recent exception with a very good sales organization

9:33 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

Chris Degnan · May 23, 2026

Hire salespeople out of companies like MongoDB and Wiz because their sales leaders, though tough, are MEDDIC disciples who develop their people and hold them accountable

Those leaders develop the crap out of their people, which is what produces a future VP of Sales

26:22 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

Kevin Egan · Jul 12, 2023 · hedged

The kind of sales rep you need is determined more by company stage than by whether the motion is PLG or enterprise

Early on you need 'renaissance reps' with wide breadth who enjoy building; at scale you get reps focused on quota and paycheck

Scope: reps in enterprise, later-stage teams do tend to be more experienced and account-focused

17:31 20Sales: Slack, Atlassian, Dropbox: Five of the Biggest Lessons on Starting, Scaling and Managing Sales Teams from 25 Years Leading the Best with Kevin Egan, Global Head of Enterprise Sales at Atlassian

Kevin Egan · Jul 12, 2023

Coin-operated, quota-obsessed reps are a liability in a company's early days but are fine and expected later as the sales organization scales

Early days are about who builds the best connection between a developing product and potential customers; later, specialization means the rep's job is simply to bring in customers and grow revenue, and they need to make a living

Scope: dislikes the term 'coin operated' itself

18:30 20Sales: Slack, Atlassian, Dropbox: Five of the Biggest Lessons on Starting, Scaling and Managing Sales Teams from 25 Years Leading the Best with Kevin Egan, Global Head of Enterprise Sales at Atlassian

Harry Stebbings · Nov 10, 2023

Sales leaders are usually boxed into a single company stage, making someone who has scaled a company across the full life cycle extremely rare

9:04 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

Julian Teixeira · Mar 7, 2025

A playbook is worthless without skills development, and it must start with hiring people with the right intellect, curiosity and discipline for the current phase of the journey.

You're hiring people to sell, not to take orders; skill and industry knowledge are built on the base of the right person, and no playbook can solve for the wrong hire.

Scope: right people for the right phase of the journey

6:16 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

Mark Goldberger · Apr 19, 2023

Every subsequent hire should raise the bar for the entire team — if they don't have potential to be as good or meaningfully better than everyone in seat, don't hire them

He's made the mistake of settling for B players himself

46:01 20Sales: Why You Should Never Hire a VP Sales First, How To Create Urgency in a Sales Process, How to Do Traditional Outbound 10x Better, Why Revenue Doesn't Matter with Your First Customers | Mark Goldberger, Head of Enterprise Sales @ Ramp

Chad Peets · Aug 23, 2024 · hedged

In hindsight, Snowflake could have raised the hiring bar higher during its fastest scaling periods

Scope: particularly in the early days of filling seats

39:36 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

Kyle Norton · May 30, 2025

The main mistake founders make on their first sales hires is settling for a body in the seat instead of holding a very high bar.

Recruiting is extremely hard when you're early stage with no traction or brand equity, which makes the temptation to compromise on a candidate with a jumpy resume and adjacent experience overwhelming.

9:31 20Sales: From $2M ARR to $40M ARR: The Playbook | How to Use AI To Supercharge Your Sales Team | Why Pipeline Reviews are BS | The Sales Call Script that Closes 99% of Prospects and How to Hire the Best Sales Reps with Kyle Norton, CRO @ Owner

Stevie Case · Jan 25, 2023

The most important trait in early sales hires is whether the person is a hunter rather than an order-taker; hunters outperform in every scenario

Early-stage selling requires the grit to open doors with no existing demand

Scope: about early sales hires specifically

0:00 20Sales: Why You Should Not Do PLG and Enterprise Sales at the Same Time | How To Move Into Enterprise Sales Gradually | How To Make a Comp Plan For Sales Teams | Why Discounting is Good and Can Be Used with Stevie Case, CRO @ Vanta

Stevie Case · Jan 25, 2023

The most important trait in early sales hires is whether they're a hunter versus an order-taker

The grit to open doors and hunt makes that person succeed over others in every possible scenario, so you need someone who doesn't expect business to come to them

Scope: early hires specifically

22:38 20Sales: Why You Should Not Do PLG and Enterprise Sales at the Same Time | How To Move Into Enterprise Sales Gradually | How To Make a Comp Plan For Sales Teams | Why Discounting is Good and Can Be Used with Stevie Case, CRO @ Vanta

Stevie Case · Jan 25, 2023

Order-takers no longer have a place on sales teams; every rep now has to be a hunter and grit will become far more important over the next eighteen months

Macroeconomic shifts mean we're no longer in a growth-at-all-costs world where business just comes to anyone, so everyone must be accountable for cracking doors

Scope: order-takers historically had value in early-career, high-velocity businesses with a clean playbook

23:24 20Sales: Why You Should Not Do PLG and Enterprise Sales at the Same Time | How To Move Into Enterprise Sales Gradually | How To Make a Comp Plan For Sales Teams | Why Discounting is Good and Can Be Used with Stevie Case, CRO @ Vanta

Carlos Delatorre · Jan 24, 2025

Hiring an AE who has never built their own pipeline is a non-negotiable disqualifier

If they say they'll do it, they just don't know how hard it is or don't remember — maybe they only did it as SDRs long ago; that's a really big risk

11:03 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

Carlos Delatorre · Jan 24, 2025

It is a non-negotiable to only hire reps who have already done pipeline generation successfully; you cannot teach it to someone who has never done it

Without having lived through the 'dark lonely room' of 19 unanswered calls and then experienced the pride of a self-generated closed deal, a rep is unlikely to make the 20th call or persist toward PG excellence, even if they say they're willing upfront

20:13 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

Carlos Delatorre · Jan 24, 2025

Hiring a salesperson based on their senior relationships and prior-employer track record is a recurring mistake, because relationship sellers often lack the pipeline-generation skills to cold-approach strangers, deliver a value prop and secure meetings.

He hired an expensive EMC rep for his relationships; three months of steakhouse lunches with senior contacts irrelevant to the product produced nothing, and it turned out the man simply couldn't build pipeline.

Scope: drawn from an early-career startup hire

54:24 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

Jesse Zhang · Sep 19, 2025

Clock speed — how fast someone thinks and learns — matters far more in hiring than domain experience or industry-specific selling ability, across every function including sales and marketing.

Their top sales reps are simply very smart people who reason from first principles and move aggressively.

Scope: concedes it may no longer be a hot take as more people buy into it

40:57 20VC: Why 90% of Founders Build Startups Wrong | Why AI Growth Rates are Sustainable & Remote Work is BS and the AI Talent War | Competing with Brett Taylor and Sierra: Who Wins the Customer Service War with Jesse Zhang, Decagon

Jesse Zhang · Sep 19, 2025

Their hiring mistakes came from not having crystallized their own culture, so they selected for industry knowledge instead of cultural fit like clock speed.

They hadn't articulated the clock speed concept until recently, so they screened on the wrong attributes.

Scope: still thinks highly of the people who left

42:34 20VC: Why 90% of Founders Build Startups Wrong | Why AI Growth Rates are Sustainable & Remote Work is BS and the AI Talent War | Competing with Brett Taylor and Sierra: Who Wins the Customer Service War with Jesse Zhang, Decagon

Becca Lindquist · May 2, 2026

The worst hiring mistake sales leaders make is over-indexing on the candidate's last company and a fixed hiring profile, which produces a hundred of the same person instead of high-slope people who push the envelope

Leaders she has worked for refused to deviate from their profile even for high-slope individuals

61:34 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

Carles Reina · Apr 11, 2026

Tech startups are wrongly afraid to hire salespeople with 20-25 years of experience, and the 'they won't fit the business' excuse is wrong

Someone who has sold to the same financial services firms for a decade carries knowledge and relationships that can propel the whole business and shorten sales cycles by going straight to the C level

Scope: acknowledges it's a controversial view; not all such hires will fit; works for the portion who are still hungry and want meaningful work

17:16 20Sales: ElevenLabs: Why We Set a 20x Sales Quota | How to Structure Sales Compensation Plans | Customer Success: 'Total BS' or Growth Engine? | Building an AI Sales Machine: What Tools & Tactics Must CROs Adopt Today with Carles Reina

Carles Reina · Apr 11, 2026

Pairing much older, highly experienced executives with young founders can work rather than being a fatal culture clash

Google's early pairing of Sergey Brin and Larry Page with Eric Schmidt produced magic; it works when both parties want it to and you hire people on the same wavelength

Scope: requires deliberate effort and hiring for brainwave fit

18:25 20Sales: ElevenLabs: Why We Set a 20x Sales Quota | How to Structure Sales Compensation Plans | Customer Success: 'Total BS' or Growth Engine? | Building an AI Sales Machine: What Tools & Tactics Must CROs Adopt Today with Carles Reina

Sam Blond · Apr 12, 2024

There is no such thing as a perfect candidate; founders should explicitly decide which criteria they are willing to sacrifice on and which they are not, then solve hard for the latter.

Every hire involves sacrifices, so the discipline is in choosing where.

Scope: about early hires

24:47 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

Chad Peets · Aug 23, 2024

Hiring managers who hold out for a candidate who checks all ten boxes end up making worse hires than those who balance speed and bar

They run a hundred interviews, fail to fill the role for nine months, then get desperate and hire someone who checks two of ten

Scope: it's a balancing act, not a licence to lower the bar

39:46 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

Unknown · Nov 16, 2022

The first sales hire at an early-stage company has to personally do enablement, sales ops and sales finance badly rather than well, and that is the necessary path to earning headcount for real specialists

Those functions simply don't exist yet, and you have to get the motion off the ground to prove you can justify additional resources and experts

Scope: early stage, before any customer-facing team exists

Kim Graves · Jun 27, 2025

The earliest sales hires should be adaptable generalist 'Renaissance reps' hired to learn, not traditional coin-operated reps expected to build the playbook

Early sales is a learning stage like the first units off a manufacturing line — expensive but highly informative — and it requires people skilled at collaborating with marketing, product and engineering while talking to customers

Scope: applies to the first three to four reps

19:35 20Sales: How to Layer Enterprise Sales on PLG | How to Sell AI Tools To Enterprises That Are Scared | Should Reps Own Their Own Pipeline | Mistakes All Founders Make When Moving From Founder-Led to Rep-Led Sales with Kim Graves

Jeanne DeWitt Grosser · Mar 9, 2022

Early-stage sales hires should be product-oriented nerds who go deep on the product and can articulate the vision like a founder would, not polished enterprise sellers

At early product-market fit you need someone who can convey product capabilities and vision the way a founder does

Scope: specific to early product-market-fit stage; different from what you need at scale

8:28 20 Sales: The Stripe Sales Playbook; Who Should Create It, When Should it Be Done, Where Do Many Go Wrong | How To Identify 10x Sales Hires and How To Structure the Hiring Process in Sales with Jeanne DeWitt Grosser, Head of Americas Revenue & Growth @ St

Jason Lemkin · May 6, 2022

Founders without sales DNA can succeed by bringing in an early, almost-cofounder-level salesperson, but hiring that person off LinkedIn or Craigslist is what fails

Algolia's engineer founders weren't great at sales and brought in a chief business officer as effectively a late cofounder as employee one or two

Scope: applies when founders lack sales DNA; person must be near-cofounder caliber, hired very early

10:41 20VC: Why the Traditional Seed Fund Model No Longer Works, Why Multi-Stage Funds Investing at Seed Bring Signaling Risk but also Less Pressure, The One Criteria All Potential Sales Hires Need to Have and The Clear Signs of 10x Sales Hires with Jason Lemki

Kyle Norton · May 30, 2025

Hiring very senior, highly experienced reps has worked less well for Owner than hiring reps with two to four years of experience

Scope: specific to Owner's current stage

57:27 20Sales: From $2M ARR to $40M ARR: The Playbook | How to Use AI To Supercharge Your Sales Team | Why Pipeline Reviews are BS | The Sales Call Script that Closes 99% of Prospects and How to Hire the Best Sales Reps with Kyle Norton, CRO @ Owner

Kyle Norton · May 30, 2025

Senior reps fail in a highly systematized, coaching-heavy sales org because they insist on their own methods and can't outperform the company's system, while earlier-career reps are more coachable and ramp faster

Experienced reps executing their own skills outside the framework produce worse results than a newer rep who runs the playbook as designed; Owner coaches weekly with monthly report cards and development plans, and some senior sellers simply opt out

Scope: not true all the time — two of their best reps had extensive restaurant tech experience; specific to Owner's current stage

58:34 20Sales: From $2M ARR to $40M ARR: The Playbook | How to Use AI To Supercharge Your Sales Team | Why Pipeline Reviews are BS | The Sales Call Script that Closes 99% of Prospects and How to Hire the Best Sales Reps with Kyle Norton, CRO @ Owner

Dan Fougere · Nov 22, 2024

Discipline is the key trait to hire for in salespeople

His teams are asked to do hard things — outbound, qualifying, accountability, accurate forecasting — which is why they get different results from most sales teams

54:19 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

Harry Stebbings · May 2, 2026

Athletes make good hires because they have the discipline to do the work when no one is watching

Almost all of an athlete's time is spent alone in the gym at 5am, with visible performance being rare

21:37 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

Chad Peets · Jan 9, 2026

The people worth hiring are obsessive to an unhealthy degree — thinking about work the moment they wake up, at 3am, at 10pm

He is that way himself, waking up obsessed with making sure things are done correctly, and needs people wired the same way

0:00 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

Chad Peets · Jan 9, 2026

The salespeople worth hiring are ones who are 'a little fucked in the head' — obsessively consumed by work at all hours

Chad wakes at 3am already thinking about work and can't help being obsessed with doing things correctly; he needs people wired the same way

11:59 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

Ishan Mukherjee · Apr 4, 2025

Founders should hire salespeople who already use AI tools in their personal lives, because those who don't see the alpha personally won't get it at work

Personal adoption is a proxy for whether a rep is future-proof and understands where the world is going

43:51 Personal ai adoption signals a future proof rep

Maggie Hott · Dec 14, 2022

A second viable first-sales-hire profile is someone one to two years into frontline management with a proven AE track record who is betting on growing into the head of sales role

They're not far removed from rolling up their sleeves and building, but already know how to manage, so you can hire people under them without teaching management

35:20 Junior frontline manager betting on growth into head of sales is a viable first hire

Maggie Hott · Dec 14, 2022

The single most important trait in early-stage sales hires is the ability to deal with ambiguity

In a company being built, things change every day, week and quarter, and many people who say they want hypergrowth cannot actually handle the constant thrash

37:42 Ability to handle ambiguity is the single most important early stage hiring trait

John McMahon · Nov 28, 2025

The best salespeople are not always athletes and not always men — some of the strongest reps he's had were women

55:14 No demographic archetype predicts performance

Chad Peets · Aug 23, 2024

Great culture means winning, world-class peers, development and meritocracy — and he will not hire candidates whose definition of culture is benefits, parental leave and being home by 4pm

Those candidates aren't the profile that does exceptional things, even though their preferences are legitimate

42:15 Hire only those who define culture as winning and meritocracy

Carles Reina · Feb 14, 2026

When inbound leads already know your product, the job is convincing them to sign, not educating them — which requires a different rep profile than product-led sales

Inbounds already know what ElevenLabs is, so it's less about the product and more about closing the contract

51:52 Inbound educated buyers need closers not educators

Doug Adamic · Sep 8, 2023

The best sales teams blend reps with industry/domain experience and reps with segment experience but no industry baggage

Industry expertise is needed to sell to the office of the CFO, but a full team of such people would carry preconceived notions about a genuinely new solution; the mix produces the most innovative sales campaigns and distribution models

43:49 Blend industry experts with unbiased outsiders

Frank Fillmann · Mar 22, 2023

Industry experience and the ability to build client trust and relevancy matter more than experience selling deals of a given size.

If you understand the customer's needs you can reverse-engineer everything else more easily than someone with big-deal experience who doesn't understand what will make the customer successful.

48:16 Industry relevance and trust building outweigh deal size experience

Chris Degnan · May 23, 2026

Hiring a young up-and-comer as first head of sales no longer works as well, because there's no time to sequence markets and they've never run an international team — which is why founders now pay experienced global CROs enormous sums

Companies need global market share ASAP, so the scarce experience of having ramped North America, Europe and APJ commands huge packages

43:25 Global scaling experience required in the first sales leader

Ron Gabrisko · Aug 4, 2025

Unless you have funding to support the team they will want to build, skip the very senior sales leader and hire a great hands-on first-line manager instead

Very senior sales hires will want to hire a bunch of people underneath them

10:11 Unless well funded skip the senior leader hire and choose a hands on first line manager

Unknown · Nov 16, 2022

The best seller at a PLG company operates like an extroverted user researcher: interviewing front-line users, synthesizing those conversations into an insight, and taking it up to the CIO.

It gives the executive buyer a unique insight about their own company they could never have gotten on their own, which earns the live conversation.

Carlos Delatorre · Jan 24, 2025

Founders should hire very junior reps before messaging and playbook are refined, accepting they'll have to do heavy lifting on training

Junior hires are happy to be at their first tech company; training them and refining the message is a part of the journey only a founder can do well

7:22 Very junior reps hired before the playbook exists

Harry Stebbings · Aug 2, 2024

Matching the salesperson's ethnicity and language to the target customer dramatically increases engagement, as in Allo's strategy of sending Chinese sellers into Chinese restaurants

People want to buy from people who are like them, and this effect is amplified when the customer is an immigrant business in a foreign country

36:04 Matching sellers ethnicity and language to target customer increases engagement

Shaunt Voskanian · Mar 21, 2026 · hedged

In an early-stage product-led motion where customers pull the product, the rep job can be done by a relatively wide population who are trained, curious and have the right personality — twenty years of sales experience is not required, even though parts of the job are hard

The job is knowing the product deeply, making customers happy and supporting viral expansion, which many people can learn if brought in and trained

24:41 Plg pull motions can be staffed by a wide trainable population

Kyle Norton · May 30, 2025

The best BDR hires are the top performers at the #2 or #3 company in a category, because succeeding with an inferior product proves sales craft and grit that transfers to a category-leading product

Being the number one BDR at a second- or third-place company is hard; those people are well-trained and gritty, so pairing them with a great product makes them take off

24:37 Top performer at a second or third place company signals transferable grit

Dan Fougere · Nov 22, 2024

Very junior salespeople can close very large deals given the right training and leadership, contrary to the conventional view that only senior reps can do big deals

At his last company multiple reps with low single-digit years of experience closed million-dollar-plus first deals; with a great playbook, framework and training you get more productivity per CAC dollar out of junior people

64:55 Junior reps can close big deals with training

Jeanne DeWitt Grosser · Mar 9, 2022

The biggest mistake founders make hiring sales teams is failing to ensure cultural alignment and to integrate sales into the rest of the organization

34:18 Cultural alignment and org integration first

Kim Graves · Jun 27, 2025

Early sales teams should mix career stages, selecting for aptitude for learning and excitement about building rather than seniority or desire to earn a lot

You want a diverse sales team, and making a lot of money isn't the point in the first year of sales

20:54 Mix career stages select for learning aptitude not seniority or pay

Becca Lindquist · May 2, 2026

A career built consecutively within one domain makes a candidate an obvious must-hire for companies in that space

A recruiter in that space can see the accumulated domain expertise laid out and will do everything to hire that person

11:39 Consecutive domain expertise makes the candidate

Harry Stebbings · Jan 9, 2026

The hiring sweet spot is immigrants — specifically Asians and Eastern Europeans — who are very young, around 23 or 24

That is the profile that has worked successfully for his own team

11:28 Young immigrant hires are the highest performing profile

Chad Peets · Jan 9, 2026

A candidate with no prior sales experience is too risky to hire into a field or inside sales role

You can teach a lot, but you have to know whether they can actually sell, and that requires prior sales experience

15:28 Prior sales experience is a hard requirement

Chad Peets · Jan 9, 2026

Hiring has gotten harder because the spec is now narrower: you need more senior reps who can handle large complex deals but who are still willing to do the grunt work of pipeline generation

Early-stage big deals demand seniority, but the stage of company still demands self-generated pipeline

24:02 Seniority for big deals plus willingness to self prospect

Ashley Kelly · Jun 7, 2024

A company's first sales-development hire should be a junior AE who has prospected and can close, not a fresh graduate or someone in their first SDR role

The first hire has to build sequences, make the cold calls themselves and help build the process before you scale; later SDR hires can be less experienced once traction is proven

14:09 First sales development hire must be a junior ae who can close

Matt Rosenberg · Oct 4, 2023

Startups should not hire their first sales executive from Google, Amazon or Facebook; ex-bankers, ex-consultants and ex-lawyers are better first sales hires

People who brand themselves 'ex-Google' on LinkedIn are associating themselves with a business success that was not theirs

0:00 Analytical non sales backgrounds over big company pedigree

Matt Rosenberg · Oct 4, 2023

A founder's first sales hire should be a sales leader rather than a junior rep

The junior rep will ultimately be replaced and hit a ceiling, creating internal churn and burnout; a more senior hire can see patterns, scale the team faster, and will develop the junior people underneath them into directors

17:03 Hire a leader first not a junior rep

Matt Rosenberg · Oct 4, 2023

The second most important sales hire is a great sales operations lead to partner with the first commercial hire

Sales ops is a different skill set that documents the process, motion and stages in the background; separating the process-builder from the customer-listener gives you the best of both worlds

18:29 Sales ops lead as the second commercial hire

Matt Rosenberg · Oct 4, 2023

Sales needs more women in leadership, and hiring parents of young children — mothers especially — produces the most efficient sales executives

They multitask, know how to drive behavior, listen and have empathy, and will get more done in an eight-hour block than you'd imagine

47:06 Hire more women and parents of young children