How should startups evaluate and select sales candidates?

Kevin Egan · Jul 12, 2023

A candidate who focuses too heavily on the comp plan during closing is a red flag; you want someone excited about the company's long-term journey

The comp plan only represents this moment in time — if the company succeeds the jobs get bigger — so what matters is total rewards and the career benefit of joining a rocket ship

Scope: comp plans still need to be fair — you cannot hire the best without a fair plan

20:35 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

The compensation negotiation is a diagnostic moment revealing a candidate's motivations, and a candidate focused purely on OTE dollars is a concern

If they aren't excited about equity and the future opportunity, they may lack staying power through a hard quarter or the ups and downs of a startup

Scope: not a full red flag, depends where the conversation goes

18:56 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

Lori Jimenez · Aug 2, 2023

It is right to walk away from a candidate who only talks about OTE, while leaving the door open

The valley is small so you shouldn't shut doors; and in her experience no walked-away candidate turned out to be one that got away

Scope: after trying to bridge the gap

20:16 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

Chad Peets · Aug 23, 2024

You can easily detect a candidate faking a desire for growth by interrogating the reason behind each job change on their resume — bigger base salary or a raised quota disqualifies them, while moving to work for a known great leader validates them

He knows every CRO and sales organization in software, so he can verify whether the stated motivation for a move is credible

Scope: depends on the interviewer knowing the sales leaders in question

9:17 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

A candidate who is purely money-motivated and indifferent to the mission is a bad hire, because they will leave for the next higher offer

They'll just go to the next thing where they get offered more money, and he might not even get two years out of them — especially now that Owner's brand equity means founders actively try to poach and overpay its reps

55:17 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

You can screen for obsession in an interview by asking what someone's passion is and what drives them — if work merely funds an outside passion, or if the answer is just 'money,' they're not the profile

Honest answers reveal whether the person wants to be the best in the world at their craft or is working to fund something else; 'I want to make money' is obvious and uninformative in sales

Scope: assumes candidate answers honestly

12:41 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

'Money' is the wrong answer to 'what motivates you' in a sales interview — the reps you want are financially motivated but must care about their own development as much as about money

All salespeople are wired for the correlation between effort and pay, but a rep who joins purely because they think they'll earn more isn't good enough; what a company sells to candidates is that it will make them better, and reps who spend four years in that ecosystem become highly employable

41:14 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

A candidate who pushes hard on money or title during hiring is a yellow flag, because it signals mercenary rather than missionary motivation

Some mercenary instinct is normal in sales, but his best people over the years weren't thinking about money first, and people chasing maximum W2 tend to end up earning less

Scope: distinguishes money-chasing from wanting career growth, learning and development, which he views very differently

36:24 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

Cliff Weitzman · May 9, 2026

'I want to earn more money' is a disqualifying answer to why a candidate wants to join

Someone else can offer more money and they'll leave after you spent a year coaching them up; you need a differentiating reason they're at your company

39:19 20VC: What I Learned from 100 of the Best CEOs in the World | What I Learned from Staying with Mr Beast for 3 Weeks | How We Will Spend More on Tokens than Salaries with Cliff Weitzman, Speechify

Jeanne DeWitt Grosser · Mar 9, 2022

Startup interviewers get too easily enamored when candidates use the right vocabulary, and should instead probe how the candidate actually executed the thing they name

Naming a method like account-based marketing or a seven-step sales process is not evidence of having executed it; asking for the steps and exit criteria shows whether they walk the talk

13:44 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

Lauren Schwartz · Oct 19, 2022

Sales interviews should not be left open-ended for storytelling or theoretical questions; they should test specifics, metrics and repeatable performance

Any good seller can sell you a dream, and answers to questions like 'how would you ramp in ninety days' can be read in an article ten minutes before the interview

18:38 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

Mark Goldberger · Apr 19, 2023

Deal attribution on a candidate's resume is meaningless without interrogating the details — when they sold in, whether it was self-sourced, who else was involved, and whether it was land-and-expand or wall-to-wall

Companies great at product-led growth may have sold to an org when it was an SMB; the rep may not have generated or done the work on the deal

40:08 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

Harry Stebbings · Aug 2, 2023

Data is very important in candidate answers — hearing a specific quantified result (e.g. 'I increased net revenue retention by 12% through these three channels') is something the speaker loves to see

17:00 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

Lori Jimenez · Aug 2, 2023

Candidates who give canned, shallow interview answers without concrete customer and team stories will perform for a while and then fizzle out

Lack of specific customer engagement stories signals there isn't enough depth behind the polished answers

Scope: about sales hires

22:21 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

Cristóbal Valenzuela · Aug 28, 2023

Interview processes should weight demonstrated doing over talking, because many people are great at interviewing and saying what you want to hear

People skilled at interviews can tell you what you want to hear, so you need to ask them to show you they can do the work right now

22:32 20VC: Why AI Models are not a Moat, Where Does the Value in AI Accrue; Startups or Incumbents, What the World Has Got Wrong About AI, Why AI Needs a New Story and Who is the Right People to Tell it with Cris Valenzuela, Co-Founder & CEO @ Runway

Steve Goldberg · Dec 13, 2023

Sales candidates should be run through a mock discovery call and then made to present the unique value proposition, the business case, and specifically the 'how' — not just the 'what'

People don't buy features, they solve problems, and it has to be one of the top three problems the company has, so the ability to run discovery and articulate execution is what matters

19:18 20Sales: How to Close Sales When Selling to CFOs, How to Guarantee You Win Every Renewal, Core Questions All CFOs Ask Today When Buying, Why Revenue Operations is the Most Important Role in a Company with Steve Goldberg, CRO @ Salesloft

Chris Degnan · May 23, 2026

You can distinguish a real seller from an order taker by asking for two to three new logos opened in the last 24 months and then probing on who the champion and economic buyer were

Candidates who faked the deals will falter under the follow-up questions, revealing they're lying

6:54 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

Harry Stebbings · Jul 21, 2023

Serial short stints of twelve to eighteen months on a CV are a negative signal; long ten-year tenures signal quality

Scope: his personal read of CVs

5:27 20VC: Why Hiring in Tech is Broken and Founders Need to be as Good at Firing as they are Hiring, Why Product Differentiation is Unsustainable & Why the Current Generation of Tech Employees are Entitled and What Needs to Change with Jean-Denis Greze @ Plai

Dan Fougere · Nov 22, 2024

Discipline is detected by evidence of doing something hard and sticking with it — fitness, a seriously pursued hobby, or staying through a full four-year vest at a startup through the hard times

Startups always go through periods harder than expected; staying is like finishing a university degree, whereas leaving every 18 months shows the opposite

Scope: fitness is not a universal signal

56:01 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 · Nov 22, 2024

Candidates who move jobs every 12–18 months ('bouncers') have accomplished essentially nothing

With three months of onboarding and three months of offboarding, they were only fully productive for about six months

56:52 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

Ron Gabrisko · Aug 4, 2025

Candidates with a string of one-to-two-year stints won't last at Databricks; he screens for evidence of grit and for data/AI technical backgrounds

A salesperson who already has data and AI technical capability ramps far faster than someone who must learn the entire technology space

32:38 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

Shaunt Voskanian · Mar 21, 2026

A resume with repeated short 12–18 month stints is a strong negative signal when hiring sales reps at scale

Hiring at scale means you have to weight what the pattern on paper tells you, even though there are arguments for keeping an open mind

Scope: acknowledges some people disagree; specifically when hiring at scale

27:43 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 · Mar 21, 2026

Defending short-tenure resumes is bullshit — one short stint can be explained by culture or family, but four in a row is genuinely telling

A single instance has innocent explanations; a repeated pattern does not

28:22 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

The speaker's biggest red flag on a sales candidate is short job tenure — roughly 13 months at each stop

7:57 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

Succeeding for seven years at a mediocre company is evidence of grit and a strong hiring signal

8:18 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

Jordan Van Horn · Aug 17, 2022

In early interviews you should sell the reality and the problems of the company rather than only the dream, and let candidates self-select in or out

Telling the truth applies 'negative pressure' — candidates have to sell you on why they still want in despite the mess, and the ones whose eyes light up at the problems are the ones who belong; the ones asking how many leads they'll get won't make it

Scope: early-stage company (two years old); he's unsure whether opening every first interview with the company's problems is a good habit

23:30 20 Sales: Three Reasons Why Sales People Fail | The Two Things That Matter When Hiring Sales Leaders | Why Revenue, Discounting and Price Do Not Matter in the Early Days with Jordan Van Horn, Revenue Leader @ Monte Carlo

Ben Fiechtner · Aug 2, 2024

Being brutally honest about the company's problems in an interview is the best way to reveal whether a candidate wants a perfect quota and territory or sees problems as an opportunity to stand out

How curious they are about the company after hearing the unvarnished picture shows their attitude

38:46 20Sales: 12-Week Step-by-Step Framework to Crush Every Sales Quarter | Moving from SMB to Enterprise: How and When | Verticalised Sales Teams: Why They are a Gamechanger and How to Build Them with Ben Fiechtner, CRO @ Clari

Dan Fougere · Nov 22, 2024

Candidates should be told during the process that this isn't a sit-back-and-enjoy-the-ride team, but a leader should not frame the job as beating people up

54:43 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

Eléonore Crespo · May 9, 2025

Candidates should be shown explicitly, in a written deck, how hard the job will be and what values the company holds, before they join

Learned from many hiring mistakes over six years — making the impossible problems and the values explicit lets candidates self-select out if they disagree

Scope: includes team-specific problems the hire will own

27:51 20VC: Four Traits of the Most Successful Founders | How to Hunt and Close Talent Like a Pro and Where All Founders Go Wrong | Lessons Raising $397M From the Best Investors in the World with Eléonore Crespo @ Pigment

Alan Chang · Jan 5, 2026

The best interview signal is whether a candidate physically leans in when told about the company's ambition and the hard work required — and you should only hire those who lean in

Body language and facial expression when hearing the ambition reveal genuine appetite for the work

27:34 20VC: $0-$260M in Revenue in Three Years: How We Did It | You Need to Work Weekends to Win — Most Founders Aren't Ambitious Enough | The Revolut Playbook: Speed, Urgency, Extreme Ownership, and Zero Excuses with Alan Chang @ Fuse Energy

Chad Peets · Jan 9, 2026

You must tell sales candidates upfront that an eight-hour day and hiding are not possible, because anyone like that will be found out fast, won't make it, and will hate the job

Screening on intensity honestly at the front end saves both sides — the environment surfaces low-effort people quickly regardless

Scope: applies to high-intensity companies like xAI

9:40 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 · Apr 11, 2026

Telling candidates upfront that the job will be extremely hard and demand huge hours reduces sales churn rather than deterring good hires

It filters out people who don't want that kind of life, and the people who stay love it

40:48 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

Jeanne DeWitt Grosser · Mar 9, 2022

A sales interview loop should split into a project review plus interviews testing sales skills and alignment with company operating principles, using behavioral questions about past work

Behavioral questions about how candidates solved past problems reveal whether they'd approach the job the way you want it done at your company

Scope: roughly four interviews after screens; Stripe's structure

12:20 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

Mark Goldberger · Apr 19, 2023

The right enterprise sales hiring process is a 30-minute qualification call on caliber and gravitas, then a deep hour on why/how questions, then meetings with other internal stakeholders, then a challenge in front of a panel up to C-suite leadership.

Enterprise reps act as quarterbacks working with other people internally and externally, so you need to see how those relationships form and whether they can play off the dynamics.

Scope: framed for startups hiring enterprise reps

31:53 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

Coachability and EQ are best vetted with non-leading situational questions ('you were stuck in a deal, then what?') where you look for ownership and behavior change rather than externalization of blame.

A candidate who says the loss was a one-off that couldn't be prevented is fundamentally different from one who changed their process, worked with their manager, and got to the economic buyer earlier in the next deal.

Scope: interviewer must not lead the candidate

27:11 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

Kevin Egan · Jul 12, 2023

Hiring great salespeople is fundamentally a matter of process and discipline, requiring a multi-step process where a candidate meets five or six people across five or six steps

You need to get to know how a candidate approaches a customer, understands business problems, and presents differentiated solutions

13:54 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

A sales interview process should be broken into chunks: first vetting role-related knowledge, then probing how the candidate achieved outcomes, especially through losses

Many candidates claim they want startup chaos but haven't really navigated it; peeling back how they handled something hard reveals whether it energizes them or makes them run

14:50 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

Kim Graves · Jun 27, 2025

Past behaviour is the best predictor of future behaviour, so problem-solving should be assessed by asking for concrete past stories such as 'tell me about a time you weren't set up for success'

Such stories reveal both whether they solved the problem and whether they took accountability or played the victim, and whether there is a pattern of persevering through ambiguity

23:16 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

Alan Chang · Jan 5, 2026

Hiring should work by defining the required skills, assigning the company's best person in each skill to assess it, grading candidates per stage, and setting compensation directly off the grades rather than comp bands

Ultimately you are buying skills, so the price should track the assessed skill level

Scope: describes Fuse's own process

28:56 20VC: $0-$260M in Revenue in Three Years: How We Did It | You Need to Work Weekends to Win — Most Founders Aren't Ambitious Enough | The Revolut Playbook: Speed, Urgency, Extreme Ownership, and Zero Excuses with Alan Chang @ Fuse Energy

Brendon Cassidy · Mar 8, 2024

Your first five sales hires should never come from outside your network — only people who worked for you or are vouched for by someone you trust

These are foundational hires you can't afford to get wrong, salespeople are notorious liars on resumes, and assessing them cold is extremely hard — roughly 95 of 100 can't do the job

Scope: first five sales hires specifically

15:06 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

Brendon Cassidy · Mar 8, 2024

Founders without a network should recruit five advisors or influencers in their space as equity-holding partners to source sales hires

Their recommendation carries more credibility and their voice more visibility than the young company's own

Scope: if you lack both a personal network and investors who can recommend

17:05 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

Brendon Cassidy · Mar 8, 2024

If you hire reps off the street rather than from your network, roughly 98% of those hires won't work out and you should expect very high turnover

Scope: applies to hires made outside a trusted network

22:10 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

Chad Peets · Aug 23, 2024

Hiring every portfolio CRO from his own known ecosystem does narrow the candidate pool, but the ecosystem itself keeps expanding as the playbook is more widely adopted

The sales playbook he uses (MEDDIC/MEDDPICC and related methods) has become more and more widely adopted, growing the pool of people trained in it

Scope: concedes Harry's point that all current CROs come from that ecosystem

10:42 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

Ron Gabrisko · Aug 4, 2025

In the $1M-$10M product-market-fit stage, the right move is to assemble a team of proven sellers from your own network and go ask existing free users what they would actually pay for

There was no playbook or revenue model yet, and Databricks had a large base of free Spark users to learn from

Scope: for the $1M to $10M product-market-fit stage; assumes an existing free/open-source user base

7:14 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

Ron Gabrisko · Aug 4, 2025

The core lesson of going from $1M to $10M is to talk to as many customers as possible and hire aggressively from your own network to generate meetings and brand awareness

Ron talked to hundreds of customers and hired ~40 people from his network in the first six months purely to set up meetings and find out what people would pay for

Scope: for the $1M-$10M stage

11:05 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

Maggie Hott · Dec 14, 2022

Giving candidates live coaching at the end of a mock exercise and observing their reaction is the best test of coachability, and candidates who make excuses, blame or get defensive should never be hired

It's fine if someone performs poorly under high-pressure conditions; what matters is whether they own the feedback and apply a growth mindset rather than writing it off

44:05 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

Maggie Hott · Dec 14, 2022

A candidate's insecurity is not itself disqualifying — what matters is whether they have received tough feedback before and how they handle and implement it going forward

She has been given really tough feedback herself and it is the handling and application that counts

46:27 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

Ashley Kelly · Jun 7, 2024

Interviewing SDRs requires assessing intangible traits rather than track-record metrics, and coachability is best tested by asking for a concrete story of failure and how feedback was implemented

Unlike closing salespeople, SDR candidates have no quota attainment or deal history to point to; asking tough, straightforward questions shows whether they can think on their feet and admit failure, which is inevitable in sales

Scope: the failure examples can be trivial and still count

17:03 20Sales: How Rippling Built Their Sales Machine: How to Hire, Train and Manage the Best SDRs, What is the Right Comp Package for Sales Teams & The Playbook to Start and Scale Your SDR Team

Ashley Kelly · Jun 7, 2024

The point of an SDR role play is not to nail the pitch but to test whether the candidate implements feedback on a second attempt

Candidates haven't been through the company's training, so failure to apply live feedback is direct evidence they aren't coachable

Scope: about 50% do the elevator-pitch role play well

20:55 20Sales: How Rippling Built Their Sales Machine: How to Hire, Train and Manage the Best SDRs, What is the Right Comp Package for Sales Teams & The Playbook to Start and Scale Your SDR Team

Becca Lindquist · May 2, 2026

Delivering critical feedback to a candidate during the interview process and watching how they react is the best predictor of whether they will work out

If they push back or get defensive it tells you what working with them will be like; defensiveness is the biggest red flag at a company like Clay where there is a lot of open white space

Scope: she currently uses it for leader hires and wants to extend it to rep interviews; better if the recruiter rather than the hiring manager delivers the feedback

14:20 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

Lauren Schwartz · Oct 19, 2022

Asking a candidate about a deal they lost is the best test of locus of control, and internal locus — accountability plus learning — is the indicator that predicts success

Candidates either take responsibility for their role in the loss or blame product, roadmap or a departed champion

Scope: at least at Fivetran

20:42 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

Asking a sales candidate to describe a deal they lost is the best first screen because it reveals whether they take ownership or blame product, competitors, or colleagues

Losing deals is normal and acceptable; what matters is whether the rep attributes the loss to their own execution (not multithreading, misidentifying the buyer) rather than to others

Scope: applies to AE-level hires

49:09 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

Lori Jimenez · Aug 2, 2023

Asking candidates about a loss — what resources they brought in and what they learned — is the best way to see past a polished sales interview performance

It reveals whether they deflect blame, whether they can reflect and turn experience into action, and how they partner with others

15:57 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

Ben Fiechtner · Aug 2, 2024

Asking a candidate the top reason they haven't had more success is the best test of growth mindset; blaming territory, quota or product is an immediate disqualification

A self-aware answer shows the candidate knows they aren't perfect and can grow

37:32 20Sales: 12-Week Step-by-Step Framework to Crush Every Sales Quarter | Moving from SMB to Enterprise: How and When | Verticalised Sales Teams: Why They are a Gamechanger and How to Build Them with Ben Fiechtner, CRO @ Clari

Harry Stebbings · Jun 27, 2025

Candidates who frame every past setback as someone else's fault are a major red flag in hiring

It's not always your fault, but there is a way to talk about it that doesn't start with 'it wasn't me'

24:11 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

Lauren Schwartz · Oct 19, 2022

Instead of accepting a candidate's supplied reference list, ask what a specific customer would say about them and then ask to contact that customer

Volunteered references are typically friends or people the candidate wrote the reference for; naming a real buyer and reaching out gives genuine clarity on what it's like to buy from them, and a candidate can't refuse

22:23 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

Harry Stebbings · Jun 7, 2023

Referees almost never state a candidate's real weakness directly, so you should ask what skills a person hired to work alongside them would need — the answer reveals the gap

The described complement of the candidate implicitly names what the candidate lacks

32:51 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

Lori Jimenez · Aug 2, 2023

You don't need many references; backdoor references from people who worked alongside the candidate are far more informative than the ones the candidate provides

Candidate-supplied references will only say good things, whereas side-channel contacts share more insight and help you see around corners

22:59 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

Chris Degnan · Nov 10, 2023 · hedged

Detecting whether a sales leader actually leads from the front is hard and interviewers get faked out; you only discover it by going into the field and meeting their team

Candidates claim they do these things and it's only when you meet the people working for them that you find they don't — which has happened to him multiple times

Scope: he still struggles with this to this day

30:57 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

AJ Tennant · Oct 23, 2024

To break through a salesperson's polished self-presentation, ask for the names of past bosses and press in the moment on what those people would say about them

Signalling you might actually contact the reference gets candidates off their sales game and into real answers

33:11 20Sales: Biggest Lessons Scaling Slack from $6M to $1BN in ARR | How to Build a Customer Success Machine and Where Most Go Wrong | The Framework to Hire All Sales Reps: Take-Home Assignments, Hiring Panels and more with AJ Tennant @ Glean

Jeanne DeWitt Grosser · Mar 9, 2022

Immersing candidates in the actual work — sitting beside salespeople, being dropped into live chat for a half day — separates real startup salespeople from people who merely want to work at a startup

Throwing them in the deep end reveals whether they can actually figure out how to respond

Scope: hard to run during COVID / remote

10:02 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

Rich Liu · Jun 7, 2023

Structured interviews alone are only half the story; a practical exercise that mimics the actual job — a mock cold call, prospecting email, or a prepped and run meeting — must be part of the process.

You need to score how they set the tone, run discovery, commercially teach, and close for next steps, which interviews can't reveal.

Scope: says small companies can do this too, not just large ones; can be split into two parts

29:39 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

Fabien Pinckaers · Feb 12, 2025

Hiring accuracy can be far better than a coin flip because competence is easy to observe directly

If you watch a developer develop for three hours you will know by the end whether they are good

Scope: applies to recruiting for smart/technical roles assessed on the job

29:20 20VC: The $5BN Company Built from the Belgian Countryside | The Story of Odoo: The Company with No Plans to Sell, IPO & Their Billionaire Founder Who Does Not Care About Money with Fabien Pinckaers, Founder & CEO @ Odoo

Ishan Mukherjee · Apr 4, 2025

Thirty-minute interviews don't work for sales hiring; either trust a network referral or run an hour-and-a-half working session, in which you can tell by the half-hour mark from the quality of the candidate's questions

Question quality in a deep working session reveals whether the rep can think and abstract

51:23 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 · Mar 21, 2025

Great candidates answer with data while weaker candidates answer with stories.

39:04 20VC: Selling Drift for $1.2BN is the Biggest Failure: What No One Tells You About Selling Your Company | Why Incumbents Are Slower & Worse Than Ever | Why the Most Valuable Companies in a World of AI Will Not Have More Than 100 People with Elias Torres

Harry Stebbings · Jan 5, 2026

Fluffy CVs are a red flag; strong candidates show specific, attributable metrics and channel-level learnings from their past work

Detailed, data-led attribution shows the candidate actually owned and understood the outcome

27:58 20VC: $0-$260M in Revenue in Three Years: How We Did It | You Need to Work Weekends to Win — Most Founders Aren't Ambitious Enough | The Revolut Playbook: Speed, Urgency, Extreme Ownership, and Zero Excuses with Alan Chang @ Fuse Energy

Alan Chang · Jan 5, 2026

Very long CVs are a bad signal — a CV should be at most one page

If Elon Musk can fit his CV on one page anyone can; padding it out reads like a first CV listing filler skills like Microsoft Word

28:16 20VC: $0-$260M in Revenue in Three Years: How We Did It | You Need to Work Weekends to Win — Most Founders Aren't Ambitious Enough | The Revolut Playbook: Speed, Urgency, Extreme Ownership, and Zero Excuses with Alan Chang @ Fuse Energy

Harry Stebbings · May 2, 2026

Data centricity on a profile — quantified results like a 387% increase in SDR volume — is a big green flag

10:47 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

Lori Jimenez · Aug 2, 2023

The case study or mock discovery stage should be run on the hiring company itself rather than a neutral or the candidate's current company

It tests curiosity and whether they did homework — they may surface parts of the company's story worth amplifying — and puts them in a high-stakes, uncomfortable situation like real sales

Scope: not looking for a perfect answer; acknowledges it is done both ways

17:29 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

Dan Fougere · Nov 22, 2024

Sales hiring should include a test where the candidate sells your own company back to you, with about three days to prepare and roughly three hours of work being the ideal effort level

Less time spent means output quality won't meet the team's bar; more time means they take too long to decide and can't move fast enough — and the exercise reveals research ability, presentation skill, whether you'd buy from them, and how badly they want the job

Scope: three hours found to be the sweet spot

57:30 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

Kim Graves · Jun 27, 2025

A mock first sales call where the candidate researches and pitches your product untrained is an effective assessment of problem solving and resourcefulness

It shows what questions they ask, whether they can adapt and learn what you actually sell, and how far they can get without guidance

Scope: used for commercial and mid-market sellers

24:39 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

Shaunt Voskanian · Mar 21, 2026

A take-home discovery-and-demo exercise is a good way to test perseverance and basic sales skills in sales hiring

It's unfair to expect a great product demo after only a few days of playing with the tool, but willingness to spend the time learning the product is itself evidence of perseverance, and the discovery approach reveals genuine curiosity

28:32 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

Sam Blond · Apr 12, 2024

His biggest hiring mistakes came from pretending that concerns surfaced during the interview process didn't really exist, and those concerns almost always resurfaced later.

Hiring pressure (needing ten more reps) plus the candidate's quota attainment made it easy to rationalize away flagged baggage.

33:20 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

You should not shortcut interview diligence for a hot candidate, even at the risk of losing them

Most hiring mistakes come from insufficient diligence, and in some global markets a wrong hire takes 12–18 months and a lot of money to replace; nothing is more important than getting the right talent

Scope: stated as his opinion; replacement cost worse in some international markets

13:58 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

Harry Stebbings · May 10, 2024

Hot candidates are like hot deals — bad decisions get made when you compress timelines and don't yet know the person

You cannot know someone well enough under time pressure

14:19 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

Harry Stebbings · May 9, 2026

Doubts felt during the interview process only get worse after hiring and should be acted on

If someone signals they really want a different role than the one they're interviewing for, they'll push for that role once inside

45:07 20VC: What I Learned from 100 of the Best CEOs in the World | What I Learned from Staying with Mr Beast for 3 Weeks | How We Will Spend More on Tokens than Salaries with Cliff Weitzman, Speechify

Mark Goldberger · Apr 19, 2023

The best interview test is a challenge where the candidate sells your own solution back to you, ideally under artificial time pressure such as cutting a 45-minute slot to 10 minutes.

It reveals whether they can research, synthesize information, and pivot under pressure, and the interviewer can verify whether what they say is correct; better to have them take that punch in an interview than with a real prospect.

Scope: acknowledges different organizations approach this differently

28:00 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

Candidates should not be allowed to pitch a product they already know cold; the asymmetric knowledge disadvantage is the point of the exercise.

Enterprise sales is hard, so he wants to see whether they can think, be challenged, and rise to the occasion rather than perform something they could do in their sleep.

29:31 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

If a candidate is pitching a product they already know, the interview panel should compensate by asking much harder questions and raising harder objections

You can accommodate for the candidate's familiarity advantage through the tone and difficulty of the mock meeting

16:24 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

AJ Tennant · Oct 23, 2024

Interrupting the interview to demand ten stack-ranked data points for prioritizing a 100-account book of business is the best test of a sales candidate

It tests creative problem solving and higher-level strategic thinking under time pressure, and maps directly to the actual job of deciding which accounts to spend time on

34:07 20Sales: Biggest Lessons Scaling Slack from $6M to $1BN in ARR | How to Build a Customer Success Machine and Where Most Go Wrong | The Framework to Hire All Sales Reps: Take-Home Assignments, Hiring Panels and more with AJ Tennant @ Glean

Ashley Kelly · Jun 7, 2024

The two good answers on SDR motivation are being money motivated or wanting title, growth and recognition; the worst answer is that a parent was in sales and thought they'd be good at it

Money-motivated candidates treat failure as not an option, and ambition for a title sustains people; the parental answer signals they don't know what they're signing up for and lack the grit the role requires

18:41 20Sales: How Rippling Built Their Sales Machine: How to Hire, Train and Manage the Best SDRs, What is the Right Comp Package for Sales Teams & The Playbook to Start and Scale Your SDR Team

Ben Fiechtner · Aug 2, 2024

A candidate being primarily money-motivated is not a problem if they check the other boxes and are open about it

Knowing their real motivation helps him judge culture fit and how to keep them motivated; most sellers try to hide it

Scope: conditional on meeting other criteria and being authentic

41:05 20Sales: 12-Week Step-by-Step Framework to Crush Every Sales Quarter | Moving from SMB to Enterprise: How and When | Verticalised Sales Teams: Why They are a Gamechanger and How to Build Them with Ben Fiechtner, CRO @ Clari

Ishan Mukherjee · Apr 4, 2025

The best reps are motivated by money and behave as owners of their book, like a founder; probing whether a candidate truly held a number and what their comp looked like separates them from people who had it easy

Compensation history gets deep into the psyche of a person and reveals ownership mentality versus people doing sales because it was easy alongside other income streams

49:55 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

Chad Peets · Aug 23, 2024

Wanting to join a hot company is not by itself a disqualifying motivation — the question is whether that's the candidate's only motivation

What matters in the interview is whether they also want development and career progression, not just to be part of something hot

41:38 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

Chad Peets · Aug 23, 2024

The idea that salespeople are purely coin-operated mercenaries who only care about making money is bullshit; the right salespeople care about the company and their careers as well as money

Money matters and salespeople are predictable to a degree, but the right salesperson is about more than just making money

Scope: concedes salespeople are coin-operated and predictable 'to a certain extent'; applies to 'the right' salespeople

59:01 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

Jeetu Mahtani · Sep 27, 2024

Sales reps do need to be money motivated, but being purely coin-operated fails long term because commissions only keep growing if acquired customers succeed and stick

Acquiring customers who churn creates a leaky funnel, so the coins stop coming

34:16 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

Rich Liu · Jun 7, 2023

Whether you run the candidate's sales exercise on your own product or on their current product should depend on what you're testing: your product tests research ability, assimilation and storytelling; their product tests core sales skills like running a meeting and discovery

Each version surfaces a different signal, so you pick based on which question you still have about the candidate

Scope: can also do a bit of both in one process

31:13 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

Kevin Egan · Jul 12, 2023

Both mock-scenario formats — a fictitious company using your product, or letting the candidate pitch their own current product — work; what matters is clearly laying out the business problems and seeing whether the rep can command the room

Each format has its own advantages; the test is about problem articulation and closing presence, not the subject matter

Scope: Salesforce used a fictitious company; Slack let candidates position their own service

15:22 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

Sean Murray · Jan 24, 2024

The assessment format should vary by role, and for a first sales rep a simple 30/60/90 day plan take-home is enough

A 30/60/90 plan lets you grasp intellectual curiosity, drive and passion for the product and problem; for early reps a CCAT or personality test may substitute

Scope: depends whether it's a first sales rep or first sales manager; 'choose your own adventure' on format

52:35 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

Rich Liu · Jun 7, 2023

Hiring should be designed backwards from the outcomes the job must produce, decomposed into required skills, then into a process that vets for those specific skills.

You need to know whether you need an evangelical narrative seller or a tactical product seller before you can vet for anything meaningful.

24:59 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

You should define the job by the outcome you need solved first, then derive the scope, title and comp from that, and use the interview process to test whether the candidate fits that description regardless of their prior title

Otherwise you hire against titles and experience rather than against the work that needs doing

33:30 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

Carlos Delatorre · Jan 24, 2025

In sales hiring, over-rotating on a candidate's past success is a trap; you should instead define the future job and assess which required skills and attributes the candidate already brings

Past success doesn't predict future success in a different job; you have to break down what needs to happen in the future and score the candidate against that

Scope: a track record of failures is still a signal to avoid

4:51 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

Elias Torres · Mar 21, 2025

Long tenure at one company is also a red flag, and even title acceleration tells you nothing on its own — you have to probe deeply into what the person actually did.

What matters is the person's slope inside the company, which a title history doesn't reveal.

38:49 20VC: Selling Drift for $1.2BN is the Biggest Failure: What No One Tells You About Selling Your Company | Why Incumbents Are Slower & Worse Than Ever | Why the Most Valuable Companies in a World of AI Will Not Have More Than 100 People with Elias Torres

Harry Stebbings · May 2, 2026

Someone who has spent 12-14 years at Salesforce is probably not great — they got stuck in their ways and settled for mediocrity

Staying that long suggests they were happy in a melee of mediocrity

Scope: self-described as possibly a bad read

6:53 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

Becca Lindquist · May 2, 2026

Spending too long at a single company is a red flag on a LinkedIn profile because it raises doubt about whether the person can do something new outside the bounds of what they built

You need to know whether they can operate outside what they've already built and done

7:09 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

Steve Goldberg · Dec 13, 2023

Top-grading interviews — a two to three hour walk through a candidate's whole life and the decisions they made at each juncture — is the best way to test for grit and competitiveness

You're looking for how people make decisions and for consistent trends across a life; hiring misses trace back to trends you spotted but didn't dig into because you were rushing to fill street quota

17:53 20Sales: How to Close Sales When Selling to CFOs, How to Guarantee You Win Every Renewal, Core Questions All CFOs Ask Today When Buying, Why Revenue Operations is the Most Important Role in a Company with Steve Goldberg, CRO @ Salesloft

AJ Tennant · Oct 23, 2024

The right way to interview sales hires is a chronological interview walking through their whole history from high school onward

Going chronologically through education and every job change builds an understanding of the candidate's deep motivations

32:25 20Sales: Biggest Lessons Scaling Slack from $6M to $1BN in ARR | How to Build a Customer Success Machine and Where Most Go Wrong | The Framework to Hire All Sales Reps: Take-Home Assignments, Hiring Panels and more with AJ Tennant @ Glean

Dan Fougere · Nov 22, 2024

Interviewing a candidate's whole life trajectory backwards — upbringing, parents, high-school interests, highest level of math taken — gives useful data points on their aptitudes and whether they make deliberate, hypothesis-driven career decisions and stick with them

In the US, reaching pre-calculus or calculus indicates quantitative aptitude, and career choices reveal whether someone is going for something great or just following recruiters

Scope: US education context for the math signal

52:14 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

Mark Goldberger · Apr 19, 2023

Great salespeople get filtered out of hiring funnels because they lack the right company pedigree or LinkedIn profile, when the real differentiators are creativity and adaptability.

He's seen people MacGyver seven-figure closed-won deals with improvised resources, and Ramp's first two salespeople grew into running half of sales/SDR and chief of staff to the CEO.

27:00 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 enterprise sales hiring mistake is assuming fit from a candidate's pedigree and accomplishments instead of testing for it.

He's seen extremely accomplished people join and be gone within six months because the fit was wrong, wasting six months of the candidate's career and six months of the company's runway.

32:48 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

Brendon Cassidy · Mar 8, 2024

The biggest sales hiring mistake is being seduced by the resume — impressive company names and titles don't tell you whether that person is still that good or was just right time, right place

Someone who was amazing at one point may not be anymore; discerning what looks good on paper from what actually plays is extremely complex

25:14 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

Sanjit Biswas · Dec 8, 2023

Skipping references to move fast on a hire backfires, because a resume shows individual achievements but not how someone operates inside an organization

Someone can look great on paper and turn out to be a terror to work with; the 'credit history' of how they behave in a team only surfaces via references

29:01 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

Kyle Norton · May 30, 2025

Companies should insist on speaking to a candidate's last two direct managers and accept no substitutes or excuses; hesitation about providing them is a massive red flag

Their mishires traced back to accepting references from managers on other teams because they were trying to move too fast

Scope: current manager can reasonably be excluded

13:33 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

Lauren Schwartz · Oct 19, 2022

An unprepared live role play of a real situation is a better interview exercise than a pitch

It recreates real life and tests whether the candidate can listen and pivot a conversation back to the customer's business outcomes

23:09 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

Harry Stebbings · Jul 12, 2023 · hedged

Making candidates sell an unfamiliar product is a better test than letting them pitch the company they already work at

Someone with years at a company can pull the wool over your eyes; an unfamiliar product forces them to think on their feet about personas, needs and competitive positioning in real time

Scope: framed as pushing back on Kevin, who he defers to as the experienced operator

15:48 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

Matteo Franceschetti · Nov 20, 2023

Short tenures are acceptable when the reason is legitimate — a former boss offering an opportunity of a lifetime, or a layoff — which is why you must probe how the candidate found each next job

49:42 20VC: The Ultimate Hiring Playbook: Five Questions to Ask Every New Hire | What Makes Truly Great Leaders and How They Give Feedback | Do VCs Really Add Value; Lessons from Hard Fundraises with Matteo Franceschetti, Co-Founder @ Eight Sleep

Chad Peets · Jan 9, 2026

A couple of short stints on a resume are acceptable if the candidate takes accountability and can explain the logic behind the move and what they got wrong, but five in a row without demonstrated success is not

He isn't looking for perfect career decisions, he's looking for accountability and sound decision process; blaming the company for lying to you is a bad answer since you made the decision

Scope: must have at least one stop with demonstrated success

21:52 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

Sean Murray · Jan 24, 2024

Sales hiring is best done by eliminating bias through a highly structured, competency-driven process, because managers otherwise hire the profile they are personally attracted to

If a sales manager has a favoured profile, that's who they'll hire — and the data shows that instinct leaves better performers on the table

46:12 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

Carlos Delatorre · Jan 24, 2025

The most common source of conflict in sales hiring decisions is that interviewers index on their own strengths and become enamoured with candidates who resemble them, missing other gaps

It's human nature; a charismatic high-EQ interviewer may miss that a candidate is weak on process, and a process-oriented interviewer may miss that a candidate is socially awkward

13:21 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

Sean Murray · Jan 24, 2024

Interview panels waste candidate time by all asking the same questions; assigning each interviewer distinct competencies and pre-set questions extracts far more data in the limited time available

A candidate only gives you so much time, so overlapping questions mean you gather less data and leave room for bias

47:26 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

Sean Murray · Jan 24, 2024

Interviewers should agree on core competencies up front and each cover a different subset with different questions on a shared scorecard, never overlapping

So the team gathers as much distinct data about the candidate as possible

Scope: roughly six to eight competencies; about nine questions per interviewer

51:49 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

Kevin Egan · Jul 12, 2023

What separates great sales candidates from good ones is consistency across every step of the process, and inconsistency between steps is a red flag

Candidates who crush the interviews sometimes flop in the mock scenario because they aren't comfortable in front of a room facing real objections

16:46 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

Sean Murray · Jan 24, 2024

Every candidate should get the identical process — same questions per competency, same take-home test, same personality test, with no tweaking

Consistency across candidates is what removes room for bias and makes assessments comparable

48:35 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

Sean Murray · Jan 24, 2024

Intellectual curiosity is the single most important trait in a sales rep, and it is best tested by the questions the candidate asks you at the end of an interview

62:19 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

Harry Stebbings · Jan 24, 2024

The best candidates always have many questions for you at the end of a process

He consistently advises founders to ask candidates for their own questions at the end, and observes the strongest ones always have plenty

62:45 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

Brendon Cassidy · Mar 8, 2024

The determining factor in hiring a rep should be a live mock pitch of whatever they sell today, and you should never hire a salesperson without it

If they can't animate a compelling story about the product they've sold for years, there's no reason to believe they'll be compelling with yours

Scope: for AE/rep hires, not SDRs

18:05 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

In a candidate case study, have the rep pitch the product from their previous company rather than pitch your own product back to you.

You are the world's foremost expert on your own product, so that exercise is almost destined for failure; whereas an exceptional rep should be able to pitch their existing product easily, and you can judge whether you'd buy it.

25:28 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

Dan Siroker · May 15, 2024

A candidate raising the topic of titles early or at all during the interview process is a red flag about their values

The best hires arrived with fancy prior titles and never brought titles up, showing they care about the problem and the company and trust that doing well will lead to growth

23:25 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless

Harry Stebbings · May 2, 2026

Candidates who negotiate hard on title tend to be bad hires, while candidates who push on salary tend to be good and know their worth

All of his mishires have been people unhappy with the title rather than the compensation

15:56 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

Jordan Van Horn · Aug 17, 2022

Case studies and tests are not useful in sales hiring; roughly 90% of the interview should be pattern-finding across relevant past experiences

What you need to learn is how someone performed, how they relate to others, and how they used past experience to acquire the skills your company needs — case studies don't get at that

Scope: specific to sales hiring

27:18 20 Sales: Three Reasons Why Sales People Fail | The Two Things That Matter When Hiring Sales Leaders | Why Revenue, Discounting and Price Do Not Matter in the Early Days with Jordan Van Horn, Revenue Leader @ Monte Carlo

Larry Shurtz · May 10, 2024

Case studies aren't necessary in a sales interview process

The case study exists to reveal mindset, thought process and the what and how — which he can get from a 45-minute conversation

Scope: allows they have value for some, and members of his own team use them

17:54 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

Ben Fiechtner · Aug 2, 2024

The best sales interview exercise is having the candidate present an account plan and executive point of view for a real account in their prospective patch, prepping the hiring managers as if for an executive meeting

It reveals how the salesperson preps and whether they can build a unique, pointed executive point of view that would both win the meeting and drive client value

Scope: interviewers play themselves rather than a fictional persona

43:26 20Sales: 12-Week Step-by-Step Framework to Crush Every Sales Quarter | Moving from SMB to Enterprise: How and When | Verticalised Sales Teams: Why They are a Gamechanger and How to Build Them with Ben Fiechtner, CRO @ Clari

AJ Tennant · Oct 23, 2024

CEOs interviewing senior leaders should give them the company's top three real problems and ask them to present a solution to the leadership team

Leadership interview time is precious and often leads nowhere; this approach both tests the candidate and generates useful ideas even if they aren't hired

Scope: framed as feedback on his own Glean interview process

44:08 20Sales: Biggest Lessons Scaling Slack from $6M to $1BN in ARR | How to Build a Customer Success Machine and Where Most Go Wrong | The Framework to Hire All Sales Reps: Take-Home Assignments, Hiring Panels and more with AJ Tennant @ Glean

Dave Kellogg · Jan 31, 2024

The biggest mistake founders make hiring sales teams is hiring a VP on pedigree who turns out to have merely been in the right place at the right time

You want a track record of success and good brand names, but it's very hard to tell whether the candidate was driving the results or just riding along

Scope: acknowledges it is very hard to distinguish driver from passenger

66:00 20VC: The Metrics That Matter in SaaS Today; Why CaC Payback is Flawed & CAC Ratio is Better, Why You Need to Hire Three Sales Reps at a Time, How to Forecast in 2024 & Biggest Mistakes Made Forecasting & How to Make Customer Success Sell More with Dave K

Elias Torres · Mar 21, 2025

The tech industry recycles known-bad hires because employers treat a prior employer's brand name as validation instead of calling for a real reference.

People he let go for cause get hired repeatedly on the logic that 'they worked at this company so they must be good'; if anyone called him he'd tell them the truth.

37:43 20VC: Selling Drift for $1.2BN is the Biggest Failure: What No One Tells You About Selling Your Company | Why Incumbents Are Slower & Worse Than Ever | Why the Most Valuable Companies in a World of AI Will Not Have More Than 100 People with Elias Torres

Harry Stebbings · Dec 4, 2023 · hedged

There are pre-hire tells for a bad hire — a pattern of one-to-two-year job stints and negotiating for an inflated title

Scope: offered as his own personal tells

42:01 20VC: From Construction Worker to Billionaire CEO; The 21-Year Epic Journey of Procore to an $8.6BN Company, Advice from Tobi at Shopify on Being a Great CEO & Why The Idea of "Becoming an Entrepreneur" is BS with Tooey Courtemanche

Harry Stebbings · Mar 21, 2025

Candidates who bounce between jobs every year or two are a red flag on a CV, and Americans are unusually promiscuous about changing jobs.

Scope: two years is better than one year

38:21 20VC: Selling Drift for $1.2BN is the Biggest Failure: What No One Tells You About Selling Your Company | Why Incumbents Are Slower & Worse Than Ever | Why the Most Valuable Companies in a World of AI Will Not Have More Than 100 People with Elias Torres

Julian Teixeira · Mar 7, 2025 · hedged

You can find good talent among laid-off salespeople, but most companies cutting staff will have cut their bottom performers

Bottom-ranked people may be new hires still getting their bearings or have had an off quarter, especially if the company used spreadsheet math rather than evaluating individuals

Scope: depends on whether the company evaluated people as individuals or by Excel ranking

15:18 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 · Mar 7, 2025

When evaluating laid-off candidates, look for whole-division shutdowns, since a team cut entirely likely failed on product-market fit rather than individual performance

If everyone is gone it isn't really a performance layoff — the product may not have had product market fit

15:54 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

Becca Lindquist · May 2, 2026 · hedged

Acceptable tenure runs from a lower bound of about two years to an upper bound of about six to seven years; beyond eight to ten years the company has been built around the person and they find it very hard to adjust elsewhere

Someone who built that much of a company struggles to adapt to another environment — like putting on someone else's shoes with the laces and insoles all wrong

Scope: open to being proven wrong; cites a friend at Heap of 8-9 years who said he was still learning

8:05 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

Harry Stebbings · May 2, 2026

Four to five years at a company is the optimal tenure

8:09 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

You should pull the string on quota claims — a genuinely passionate seller knows every detail of their numbers, ranking, and biggest deal without checking

They're proud of it and hang their hat on it; not knowing your rank means it doesn't drive you insane not to be number one

16:01 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

Becca Lindquist · May 2, 2026

Stated quota attainment and President's Club are green flags, while a profile is a red flag when you can't tell the candidate's story — a mishmash of unrelated companies with no visible expertise being built

You want to see where the expertise is being built; a random sequence of great companies doesn't tell you that

Scope: the individual companies can all be good companies

10:59 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

Twenty minutes is enough to decide whether to hire a salesperson — you can read energy, sharpness, speed of thinking and preparation from a live pitch exercise

Asking them to pitch the company cold reveals how fast they think and how much they researched

44:29 Twenty minute live pitch is enough signal

Maggie Hott · Dec 14, 2022

The way to test whether a candidate genuinely tolerates ambiguity is to ask for concrete past examples of process change and probe how they spotted, handled and implemented it

The specifics reveal whether they are a go-getter who drives change or someone who waits and goes with the flow

38:30 Probe concrete past examples of driving process change to test ambiguity tolerance

Maggie Hott · Dec 14, 2022

Asking candidates to demo your product in the final interview round is one of the worst things a company can do

It warms them up, shows how they light up when passionate — which predicts how they present to customers — and lets the interviewer probe with questions to see how well they teach concepts to a buyer, which matters because selling technical software involves a lot of teaching

40:02 Demo in final round reveals passion and teaching ability

Lauren Schwartz · Oct 19, 2022

The best sales teams and reps come from category-creating environments where there is no pre-existing budget for the product.

Selling without an identified budget forces sellers to tie value to the product, which is what produces real hustlers.

45:09 Category creating no budget selling background is the best hiring signal

Chad Peets · Aug 23, 2024

Sales hiring must follow a fixed process with binary go/no-go decisions at each stage, and a hiring manager who can't decide after two hours with a candidate is the problem, not the candidate

Building a world-class sales machine at scale and speed requires a well-oiled process that managers don't get to deviate from

30:06 Fixed process with binary go no go gates

Chad Peets · Aug 23, 2024

Adding non-sales interviewers for culture-fit assessment is a mistake: it slows the process, risks the interviewer saying something that scares off the candidate, and creates organizational friction when their veto is overridden

If four sales leaders want to hire and one engineer doesn't, you hire anyway and have now either angered the engineer or deferred to someone who knows less about hiring salespeople

31:51 Sales leaders only no cross functional panel

Chad Peets · Aug 23, 2024

You have to hire fast to scale, but only if someone centrally owns and defends the hiring profile against new leaders bringing in their own people

A newly hired VP who's never sold the product knows the winning profile less well than the people who built the sales organization, and a CRO running 400 people has no cycles to interview every candidate

32:42 Central owner defends the profile during fast hiring

Chad Peets · Aug 23, 2024

Everyone involved in recruiting must be aligned on uniform company messaging, even though each person recruits in their own style

If managers say different things to a candidate going through the process, you lose all credibility and the candidate stops believing anything you say

38:31 Uniform company messaging across all interviewers

Sri Batchu · Jul 26, 2023

There is no inherently wrong motivation for an employee — including title, position or external validation

It's better to start from honesty and work with the incentives already in people's heads than to try to create different incentives for them, so the question should be framed non-judgmentally

29:18 No motivation is inherently wrong work honestly with existing incentives

Harry Stebbings · Nov 20, 2023

Candidates with a string of 18-month-to-two-year stints have effectively only done about six months of real work per job once ramp-up and wind-down time are subtracted

Ramp time and leaving time consume most of a short tenure

49:26 Short tenures mean most of the stated time was ramp up or wind down not real work

Matteo Franceschetti · Nov 20, 2023

Repeated layoffs on a résumé are concerning not as a verdict on the candidate's importance but as evidence about their judgment in choosing which companies to join

Being caught in three or four RIFs raises the question of how they evaluated those companies; thoughtfulness about which company to join and why is a key career skill, and a plausible dream-driven bet on a failed company is forgivable while joining a tiny debatable company after Amazon is not

50:01 Repeated layoffs across multiple companies signal poor judgment in choosing employers

Sean Murray · Jan 24, 2024

Hiring salespeople well is far more data-driven and scientific than people assume, and it starts with the language of the job description

The words in a job description determine who is motivated to apply, so attracting talent is where the process really begins; software makes the process reliable

45:01 Job description language is the starting point of data driven sales hiring

Harry Stebbings · Jan 24, 2024

A rigidly formulaic interview process loses the art of a candidate's story and your understanding of what makes them individual

By analogy: if he asked the same structured questions of every podcast guest he'd miss the fabric of what makes each person themselves rather than a robot

50:30 Rigid scorecard interviews lose the candidates individual story

Sean Murray · Jan 24, 2024

A structured, scorecard-driven interview process is worth the loss of some nuance, because unconscious bias inevitably creeps into every human-run interview

You can still capture the 'art' of a candidate's story inside a structured process, and in the limited time available he'd rather have more science and data-driven results than the unstructured nuance

50:59 Structured scorecards are worth sacrificing nuance to reduce bias

Sean Murray · Jan 24, 2024

Asking a candidate to explain a time they were told to call back in six months is the most revealing sales interview question

It exposes very quickly how that person actually operates

62:56 Call back in six months scenario question is the most revealing sales interview question

Sean Murray · Jan 24, 2024

The best answer to the interview question 'tell me about a time you were asked to call back in six months' is one where the candidate reframes the problem and teaches the interviewer something they didn't know about their own business in that moment

Most candidates just say they'd diligently follow up in six months, which exposes how they operate; the strong rep instead creates new insight on the spot

63:23 Reframing the problem to teach the interviewer something new is the best answer to the callback question

Stevie Case · Jan 25, 2023

A sales interview loop should combine functional interviews with a full interview dedicated to testing for grit, plus a case study or role play to test curiosity and discovery

Functional interviews only check whether someone can do the basic job; grit and curiosity are what actually determine success, and curiosity drives both learning and closing hard deals

27:39 Combine functional interviews with a dedicated grit interview and curiosity case study

Matt Plank · Dec 20, 2024

The strongest signal in an early-stage sales leader hire is that they were rapidly promoted two or more times at the same company

One promotion can be a mistake, but you don't get promoted twice at a high-growth company unless you're good — and rapid succession means they absorbed broken, unfamiliar scope and solved it each time

56:16 Rapid repeat promotion at one company is the signal

Jordan Van Horn · Aug 17, 2022

The first interview should screen purely for motivation, and the hiring manager should do both the motivation and track-record interviews before the candidate meets anyone else

Culture fit and possible excellence are the meat of the decision — if the manager clears those two, about half the candidates who reach the on-site will be hired

28:09 Hiring manager screens motivation and track record before anyone else meets candidate

Jordan Van Horn · Aug 17, 2022

The best interview presentations demonstrate discovery — curiosity, good questions and holding court — rather than content mastery

No one wants to listen to someone talk for an hour; showing you can ask questions and get to truth is what matters, even though it's counterintuitive in a presentation format

30:35 Presentations should demonstrate discovery and curiosity not content mastery

Jordan Van Horn · Aug 17, 2022

Employee success starts in the interview process — you should only hire people whose motivations fit the company, and simply not hire people who won't be happy there

Just as customer success starts in the sales process, understanding what someone cares about up front determines whether they'll thrive

35:56 Employee success starts in hiring only hire those whose motivations fit

Larry Shurtz · May 10, 2024

Interview teams should be kept small, with one-on-one interviews rather than panel interviews

Talent is widely available today, but dragging candidates through long processes with 'just one more interview' loses them; speed plus a defined process wins the best people

11:38 Small one on one interviews beat panels

Larry Shurtz · May 10, 2024

The three interview lines that matter most are track record led with results, which culture the candidate preferred and why, and what drives them

Sales is a results-driven business, and the culture question surfaces the candidate's actual values, which need to align

15:33 Track record culture fit and motivation are the three key interview questions

Larry Shurtz · May 10, 2024

Interviewers should repeatedly ask why rather than accept a candidate's first answer, because the nuance lives in the why

A candidate saying they're motivated by money often actually means outcomes for their family, which is a different motivation

17:22 Repeated why probing reveals true candidate motivation

Larry Shurtz · May 10, 2024

Whether a candidate can bring two or three great people with them is a strong hiring signal, and the more senior the role the more it becomes a requirement

At senior levels your network and brand are critical to building a team

18:24 Ability to recruit other great people is a hiring signal

Larry Shurtz · May 10, 2024

Compensation affordability and structure should be established early in the interview process, not at offer stage

Discovering after two months of interviewing that the comp equation doesn't pencil is a costly waste; you also need to know whether OTE or equity matters more to the candidate

19:23 Establish comp fit early in process not at offer

Larry Shurtz · May 10, 2024

He will not hire salespeople he finds offensive or abrasive, regardless of talent

If they behave that way toward him, they will behave that way with customers

29:07 Abrasiveness toward interviewer disqualifies regardless of talent

Carlos Delatorre · Jan 24, 2025

A presentation 'challenge' should come only at the end of the hiring process as validation, once the hiring team already has conviction — not early on

The challenge takes real work, so it wouldn't be fair to a candidate early in the process; its role is to make sure nothing was missed

12:23 Challenge exercise only at the end as validation

AJ Tennant · Oct 23, 2024

Hiring panels are an important part of a sales interview process

A panel replicates the customer meeting with three or four stakeholders, letting you see the candidate's IQ and EQ in reading and presenting to a room; it's a miss to hire someone whose core job is that kind of call without ever seeing them do it

40:25 Hiring panels replicate customer meetings and reveal iq eq

AJ Tennant · Oct 23, 2024

What you should screen AEs for is creative, proactive problem solving, evidenced by artifacts they built, business cases they solved, or self-initiated customer research

These behaviours reveal both creativity and genuine passion for the product

42:47 Screen for self initiated artifacts and proactive problem solving

Shaunt Voskanian · Mar 21, 2026

A candidate who isn't visibly all-in at the end of the process — especially one actively pitting you against another company — is a yellow flag you should heed

Such hires have left as soon as things got tough or the other company came back with a different offer

31:04 Lack of visible all in commitment at offer stage is a red flag

Cliff Weitzman · May 9, 2026

The best candidate answers show personal connection to the product or specific research into the company and its founders

It demonstrates a real reason they are here rather than anywhere else

40:24 Personal connection or specific research is the signal

Jeanne DeWitt Grosser · Mar 9, 2022

The first one or two interview calls with a startup sales candidate should be equal parts you interviewing them and them interviewing you, because moving to a startup is a risk you have to sell against

Joining a startup is a risk for the candidate, so the company has to sell itself before the core evaluation begins

11:20 Early interviews must sell the candidate

Kim Graves · Jun 27, 2025

A common founder mistake in sales hiring is not defining what they are looking for and falling back on surface heuristics like a flashy company pedigree or strong presenting skills

Those heuristics are surface level and lead you astray; you need defined competencies to build a process and questions around

21:35 Define competencies first avoid pedigree and presentation heuristics

Kim Graves · Jun 27, 2025

Candidates should get only a few days to prepare the mock call, not a week

Hiring processes can't be drawn out, and short deadlines test whether the candidate can be a pacesetter, which reflects the reality of the environment they'll join

25:45 Short prep window tests pacesetting ability

Kim Graves · Jun 27, 2025

The two main ways candidates fail the mock call are inadequate preparation and failing to be 'audible ready' when thrown off

Preparation shows in whether they read the customer stories, watched the published videos and signed up for the product rather than winging it or reusing an old playbook; caving on a discount question or inventing a technical answer reveals both an integrity problem and an inability to adapt

26:13 Failure modes are inadequate prep and not audible ready

Kim Graves · Jun 27, 2025

Early-stage hiring panels should include cross-functional partners the rep would work with, not only sellers, with the target competencies laid out in advance

So that everyone on the panel knows what they are looking for

27:43 Include cross functional partners with shared competency criteria

Kim Graves · Jun 27, 2025

Founders under pressure to hire salespeople should never lower the hiring bar; instead they should widen the top of the hiring funnel to see more candidates

A bad sales hire is far more costly than the delay; if five candidates a week aren't working out, you need to see ten rather than settle

41:27 Widen the top of funnel rather than lower the bar under pressure

Julian Teixeira · Mar 7, 2025

A ~29-30% non-regrettable attrition rate is what 1Password is seeing this year, and heavier investment in vetting during hiring is the response

They reach the conclusion that someone won't work out quickly, but some people are simply great interviewers

18:12 Invest more in vetting because strong interviewers slip through

Becca Lindquist · May 2, 2026

LinkedIn recommendations should be discounted when evaluating a candidate

10:15 Public recommendations carry no signal

Becca Lindquist · May 2, 2026

The key test for an early-stage sales hire is whether they can tie your product to a real business problem at a specific company and attach a dollar outcome to it, rather than talking about the product itself or pie-in-the-sky possibilities

Thinking critically about the customer's business is the differentiating skill; concrete impact framing beats abstract 'art of the possible' talk

20:08 Tie product to a quantified business problem

Chad Peets · Jan 9, 2026

You cannot hire perfectly while scaling fast, and over-scrutinizing every hire to avoid mistakes just slows the process and causes you to miss recruiting numbers

Going from 50 to 300 reps requires hiring fast, and fast hiring inevitably produces some mistakes; the alternative trade-off is worse

31:10 Accept mis hires rather than slow the process

Ashley Kelly · Jun 7, 2024

An email writing assessment is as important as the role play, and the 'why you, why now' framework remains a valuable test of whether someone will be a good SDR

Demos are booked over email; you need to see whether candidates actively read the prospect's response, mirror their language, reply concisely, and connect why-this-company/why-this-persona

22:51 Written email exercise alongside the role play

Ashley Kelly · Jun 7, 2024

Being cut in a layoff is no longer a signal that someone is a weak performer

She has hired laid-off people who performed well, and top AEs and leaders have been cut too; reputations can be verified through back-channel references

29:44 Layoff history is not a negative signal

Ashley Kelly · Jun 7, 2024

Hiring SDRs off a single 30-minute phone screen is a serious mistake

It sacrifices quality of talent to fill seats fast, and it also undermines candidate buy-in because getting a job that easily cheapens it

30:11 Multi stage process over fast seat filling