How early and on what signals should a company judge whether a new sales hire is working out?

Chris Degnan · Nov 10, 2023

You can tell quickly whether a salesperson will fail — a rep six months in who doesn't know their product on a call should be cut — and the hard part is having the guts to act on that gut read fast.

Your gut sees it early, but empathy makes you carry people who have hit their ceiling.

39:08 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

Sean Murray · Jan 24, 2024

When a sales rep isn't working out the right move is to move on and bring in new talent rather than try to repair them

44:53 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 · Apr 12, 2024

You can tell within a week whether a sales hire is good, and most people are far too nice about admitting it.

32:10 20Sales: The Biggest Sales Lessons Scaling Brex to $400M ARR, Why Startups are Doing Outbound Wrong and How to Fix It & Why Demand Gen is the Bottleneck for all Startups and How to Solve it with Sam Blond, Former CRO @ Brex

Sam Blond · Apr 12, 2024

You know whether an early sales hire will work within about thirty days regardless of sales cycle length; the commonly cited quarter or ninety days is far too long.

The signal doesn't depend on cycle length, so waiting a quarter wastes time.

Scope: especially for early hires; concedes Harry's one week may be closer to right

32:18 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 Fougere · Nov 22, 2024

Leaders almost always keep underperformers too long; the discipline is to hire slow and fire fast, and once your gut says it's a mishire you should at minimum start a documented process to find out for sure.

Human nature resists it, and in hypergrowth the pressure to hit headcount targets makes it even harder to let people go; advisors and board members give better advice here precisely because they don't carry that pressure.

Scope: acknowledges it's hard in practice; PIP partly for HR coverage

44:39 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 · Jan 9, 2026 · hedged

You know a sales hire isn't working much sooner than people admit — sometimes within ten days to two weeks

Scope: 'in the worst of cases'; framed as 'I think'

32:08 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

You should fire fast; the difference between good and bad managers is owning hiring mistakes and fixing them quickly rather than giving it more time and letting the problem fester

Pretending you didn't make a mistake and extending the rope only allows the problem to grow bigger

32:22 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

Lauren Schwartz · Oct 19, 2022 · hedged

Within the first thirty days you can sense whether a new rep will be successful, by watching how they get organized, whether they're as curious as they seemed in the interview, and whether they attach themselves to top sellers and cross-functional colleagues

These behaviors are visible leading indicators of eventual performance

29:51 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

A rep who isn't asking questions or being vocal in the first month or two is a red flag worth digging into

You need to determine whether they're silent because they understand everything or because they don't know what questions to ask — an aptitude vs attitude issue

Scope: not itself grounds for firing; recognizes not everyone is a type A gregarious personality

38:56 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

Ashley Kelly · Jun 7, 2024

Early signals of a future top-performing SDR include making calls at their desk on the floor rather than hiding in a phone booth, and proactively booking time on the VP's calendar

It reflects proactiveness and that they actually care about their career and want to learn how to stand out

Scope: applies to in-office people

36:31 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

Julian Teixeira · Mar 7, 2025

The first two weeks should be listen-and-learn on product, systems and team, and the key signal to watch is curiosity — asking lots of questions rather than nodding through training

Curiosity indicates how engaged someone is and how willing they are to be an active participant in their own success, rather than expecting a headset, laptop and 20-page playbook to make them hit target

16:58 20Sales: Everything You Know About Sales Playbooks is Wrong | How to Hire and Train Your First Sales Hires | How to Crush Pipeline and Deal Reviews as a Team | How to Structure Sales Teams and Sales Comp Plans with Julian Teixeira, CRO @ 1Password

Ishan Mukherjee · Apr 4, 2025

You can tell in a candidate's first week whether they have it, based on the questions they ask — good candidates ask about the psychology, pain and buying propensity of the customer rather than boring discovery questions

Understanding buyer pain, propensity to buy and where they are in their journey is what actually matters in selling

27:46 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

Lauren Schwartz · Oct 19, 2022

A new enterprise rep's quality can be assessed before any revenue via leading indicators: whether they progressed the first call, secured follow-up, earned the right to spend company resources on a trial, and got alignment with the economic buyer

Enterprise sales is a collection of small milestones, so process and accountability are visible long before a win

Scope: applies early in the sales cycle, before any close

28:19 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

Carlos Delatorre · Jan 24, 2025

Ramp should be decomposed into a series of early milestones so under-performance is caught in weeks, rather than waiting until 18 months to part ways

Waiting nine to twelve months to worry and 18 months to act is enormously expensive in money, the rep's time and opportunity cost; with leading indicators you can diagnose and fix, or conclude they're in the wrong role or company

Scope: milestones include training exams, role plays, first meetings booked, conversion, reaching an economic buyer by month three

37:09 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

Kim Graves · Jun 27, 2025

Onboarding should be designed around the key outcomes and leading indicators you want a new seller to hit, not around their first big sale

The first big sale is a lagging outcome; the leading indicators before it are what you can actually manage against

29:54 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

Chris Degnan · Oct 10, 2025

Scaling sales hiring requires instrumentation that measures new hires at day 1, 90 and 120 so leading indicators of failure surface early

When you hire fast, new leaders who have never managed or never worked at the company are doing the hiring, so mistakes are inevitable — you need to know who is failing and get ahead of it rather than relying on the interview process

35:02 20Sales: Scaling Snowflake from $0-$3BN in ARR | Snowflake vs Databricks: My Biggest Lessons | Why Customer Success is BS and What Replaces It with Chris Chris Degnan

Chris Degnan · Nov 10, 2023

Rep productivity should be expected on different clocks by segment: corporate reps productive in three to six months (60-day cycles), mid-market in six to nine months, and large enterprise in twelve months.

Ramp expectations should track the length of the sales cycle in each segment.

Scope: based on what Snowflake sees

40:02 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

Kim Graves · Jun 27, 2025

Onboarding outcome checkpoints let you tell quickly whether a hire is working, though the window depends on ramp — enterprise reps ramp longer than commercial reps

Checks like whether they prioritized accounts correctly and how they performed in mock calls are early signals of path

Scope: timeline varies by segment and ramping period

40:22 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

Carles Reina · Feb 14, 2026

Reps below 50% of quota who are building genuine long-cycle enterprise pipeline should be kept, not fired, because they need more ramp for harder segments

A hire from AWS looked like a miss on the numbers but was building the best UK enterprise accounts and later hit 200%+ of quota

Scope: requires diagnosing pipeline quality, not just headline numbers

22:57 20Sales: Inside ElevenLabs $330M ARR Sales Machine | The 20x Sales Comp Plan Reps Must Hit | How to Land and Expand in a World of AI | Why Product-Market-Fit is BS, Reps Should Not Be in the Office and Outbound is King with Carles Reina

Jordan Van Horn · Aug 17, 2022

A new sales hire should demonstrate tangible impact within their first thirty days, and soft deliverables like pipeline coverage numbers or a written book strategy don't count

Everyone can make an impact in thirty days — on customer calls, on the sales process, or on onboarding — and you can tell quickly whether someone is jumping in and going in the right direction or flailing

Scope: impact doesn't have to mean closing a six-figure deal in month one

41:06 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

Unknown · Nov 16, 2022

The clearest early red flag is absence of impact — every new rep can make some real impact within days, and soft deliverables like pipeline coverage or a territory book strategy don't count

Impact can show up on customer calls, in improving the sales process, or in raising the bar on onboarding itself; flailing shows up quickly against that standard

Scope: impact doesn't mean closing a six-figure deal in month one

Carles Reina · Feb 14, 2026

New sales hires should sign their first contract within their first two weeks

It was an explicit internal target and some reps signed their first enterprise contract within 72 hours; size of the contract is irrelevant

Scope: contract can be tiny

48:39 20Sales: Inside ElevenLabs $330M ARR Sales Machine | The 20x Sales Comp Plan Reps Must Hit | How to Land and Expand in a World of AI | Why Product-Market-Fit is BS, Reps Should Not Be in the Office and Outbound is King with Carles Reina

Jordan Van Horn · Aug 17, 2022

Sales organizations over-index on revenue as a lagging indicator; a well-designed sales process with discrete, measurable events gives you signal on rep quality from day one of a sales cycle

A ton happens before revenue arrives, so if each step of the process is discrete and measurable you can judge what a rep is doing with their first interactions even when the deal may close a year later

Scope: revenue still matters because it's why people get hired, fired and promoted

42:09 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

Sean Murray · Jan 24, 2024

You can tell quickly whether a sales rep is working out, even in long enterprise cycles, if you run a data-driven stage-gated process

You can see where deals fall off between stages and whether the rep is hitting the exit criteria to graduate a deal, which surfaces a talent issue fast

Scope: requires a structured, data-driven sales process with stage criteria

44:15 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

Revenue orgs should embed a certification culture and track sales-stage progression plus call recordings as the stage gates in a rep's first six months

The first six months in enterprise are critical, and testing on product and narratives plus watching whether deals graduate from stage two to three tells you what's missing

57:18 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

Sam Blond · Apr 12, 2024

Sales hires should be measured on three things — performance, effort, and attitude — and this holds for the first hire through the hundredth.

Performance is objective revenue output; effort and attitude require no skill but shape the team, so they are the fallback when performance is absent.

Scope: effort and attitude are subjective judgments

27:43 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

Julian Teixeira · Mar 7, 2025

Whether to cut underperformers should be decided on skill versus will: lacking skill amid a changing business is acceptable if the person puts in the reps, but those who blame failure on anything but themselves should be let go

Product portfolios and sales motions evolve, so falling behind on skill is forgivable if someone is willing to catch up; lack of ownership is not

Scope: it depends on the individual case

14:22 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

Shaunt Voskanian · Mar 21, 2026

Whether to fire a rep fast should depend on the cause: be very patient with reps who work hard, improve and have a growth mindset but haven't clicked yet, and move very fast on reps lacking will, attitude or effort

Great people are extremely hard to find at scale, so the alternative to a hard-working improving rep is usually worse; a rep can't control quota or enablement but can always control attitude and how they show up

51:59 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

Rich Liu · Jun 7, 2023

The biggest first-month red flag in a new sales rep is that they don't generate their own pipeline — they won't make the calls or get their hands dirty

If the expectation was set and they still aren't doing it early in their tenure, that predicts they won't build pipeline or close deals later

Scope: assuming the expectation to self-generate pipeline was set up front

39:59 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

Sam Blond · Apr 12, 2024

Even with long sales cycles, a good hire produces immediately visible leading metrics such as new opportunities created and pipeline added.

A strong rep starts pounding the phones and breaking into accounts right away, which shows up in pipeline regardless of how long deals take to close.

Scope: metrics are leading indicators, not closed revenue

30:40 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

Ashley Kelly · Jun 7, 2024

You can identify a mishired SDR by month two, judging input KPIs like calls, emails and accounts sequenced rather than stage-two output

The inputs are not hard to accomplish, so failure to execute them signals effort or another underlying problem well before output metrics show it

35:45 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

Brendon Cassidy · Mar 8, 2024

You generally know within a quarter whether a sales hire is working out

Some reps are gangbusters immediately and others take longer, but he knew the good ones early either way

Scope: you might give them more time

22:23 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

There should be no artificial timeline for firing a sales rep; you should see traction by about a quarter plus some change and full ramp by the end of the second quarter, and only then consider letting them go

If you believed in the hire you made, you should give them the natural ramp period rather than a preset clock

Scope: assumes you believed in the hire; roughly two quarters to fully ramp

24:35 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

Julian Teixeira · Mar 7, 2025

You can tell within the first three months whether a sales hire will not work out

They track ramp targets plus a set of behaviors and leading indicators predicting success over the following three months

16:23 20Sales: Everything You Know About Sales Playbooks is Wrong | How to Hire and Train Your First Sales Hires | How to Crush Pipeline and Deal Reviews as a Team | How to Structure Sales Teams and Sales Comp Plans with Julian Teixeira, CRO @ 1Password

Alan Chang · Jan 5, 2026

Formal performance improvement plans are a waste of time; a single verbal warning is enough

Most people you hire are already self-aware of where they fall short before you even tell them, so the formal process adds nothing beyond 'improve or you're out'

31:30 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

Chris Degnan · May 23, 2026

Performance improvement plans almost never work and are really a signal for the employee to leave

Scope: he has seen them work on rare occasions

32:30 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

Stevie Case · Jan 25, 2023

With long enterprise sales cycles, measuring a new rep's effectiveness requires someone experienced (founder or sales manager) close enough to deeply inspect deals rather than relying on the rep's own reporting

Left to their own devices some reps report deal progress very inaccurately — you hear 'signature by Q3' and in Q3 discover they haven't heard from the buyer in sixty days

Scope: applies to long enterprise sales cycles

36:43 20Sales: Why You Should Not Do PLG and Enterprise Sales at the Same Time | How To Move Into Enterprise Sales Gradually | How To Make a Comp Plan For Sales Teams | Why Discounting is Good and Can Be Used with Stevie Case, CRO @ Vanta

Harry Stebbings · Feb 14, 2026

You can judge an enterprise rep's quality well before deals close, without waiting out the long sales cycle

Looking under the hood at relationships, conversations, interactions and where deals stand gives you a good enough feel for how close they are

24:55 20Sales: Inside ElevenLabs $330M ARR Sales Machine | The 20x Sales Comp Plan Reps Must Hit | How to Land and Expand in a World of AI | Why Product-Market-Fit is BS, Reps Should Not Be in the Office and Outbound is King with Carles Reina

Sean Murray · Jan 24, 2024

You should know within a rep's first six months whether they will make it in enterprise; founders make the mistake of waiting a year and a half for closed deals

Signals exist in the sales process well before deals close, so there should be more stage gates

56:53 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

Dave Kellogg · Jan 31, 2024 · hedged

In enterprise sales you cannot actually know a rep is not good for six to twelve months, though you can guess much earlier from activity and pipeline

Six-to-nine-month sales cycles mean you only truly know once you have seen what they closed — talk is cheap in sales

Scope: enterprise sales specifically; early signals like pipeline and call volume give a feeling but not knowledge

31:59 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

Jordan Van Horn · Aug 17, 2022

The biggest onboarding mistake managers make is proximity — they aren't close enough to the new hire's work to tell the difference between someone being new and an actual skill gap

Distinguishing newness from a real gap requires pattern recognition managers often lack; the fix is to benchmark against your best-onboarded hires and watch the new person like a hawk

40:11 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

Unknown · Nov 16, 2022

Managers lacking pattern recognition should benchmark new hires against the two or three people who had the best onboarding and watch them closely, which reveals fit within days

It substitutes an explicit benchmark for the pattern matching experience they don't have

Patrick Forquer · May 11, 2026

You can tell within about forty-five days whether a sales rep will make it, by combining AI-scored call quality with pipeline/opportunity development

Scoring discovery framework and demo flow flags problems early, and they know what good and bad look like

Scope: decisions to move on typically made within the first quarter

38:40 20VC: Inside Legora: $100M ARR in 18 Months | Jude Law Generated $50M in Sales Pipeline: The Economics Broken Down | Competing Against Harvey, the 800 Pound Gorilla | Why Legora is Undervalued at $5.5BN with Patrick Forquer, CRO @ Legora

Patrick Forquer · May 11, 2026

The claim that long enterprise sales cycles make it hard to judge a rep may hold in traditional SaaS but does not hold at Legora, where reps are buried in deals within sixty days and top performers close within ninety

The market is being made right now with huge inbound volume, so reps aren't working cold territories with BDRs and ABM — they're in about five pilots in their first quarter, giving far more signal far faster

Scope: concedes it might still be true in traditional SaaS; conditional on the current extremely hot market

39:33 20VC: Inside Legora: $100M ARR in 18 Months | Jude Law Generated $50M in Sales Pipeline: The Economics Broken Down | Competing Against Harvey, the 800 Pound Gorilla | Why Legora is Undervalued at $5.5BN with Patrick Forquer, CRO @ Legora

Carles Reina · Apr 11, 2026

Closed revenue alone shouldn't decide whether to cut a rep — building strategic accounts and the right pipeline counts, but visible activity is non-negotiable

An empty calendar means nothing is happening; strategic account building justifies a slow number, inactivity doesn't

42:50 Activity and strategic account building over closed revenue

John McMahon · Nov 28, 2025

Reps should not be fired simply because they haven't closed by the end of the standard ramp period; people progress at different speeds and the right signal is whether they are making incremental jumps in knowledge and skill

He kept a rep at BladeLogic for 13 months against board pressure because on joint sales calls and role plays the rep visibly improved each time; the rep then closed a $1.1M and a $1.2M deal

41:20 Incremental skill progress beats the ramp deadline

Chad Peets · Aug 23, 2024

The right moment to remove a rep is when you've done everything you can to make them successful and there are no extraneous circumstances — you must first check whether the territory or account list, not the individual, is the problem

Good reps get hired into bad patches, so a good manager separates the patch from the person before making the move

35:19 Rule out territory problems before cutting the rep

Lori Jimenez · Aug 2, 2023

The signs a sales rep isn't working are the two activity metrics — pipeline acquisition and pipeline acceleration — plus whether they absorb coaching and learn from lost deals

If they're not having enough conversations or moving pipeline, there's nothing happening; and if learning doesn't pick up after proper coaching and resourcing, it's time for a conversation

28:42 Pipeline acquisition acceleration plus coachability

Chris Degnan · Oct 10, 2025

Sales reps should be given explicit, measurable expectations (calls made, pipeline generated by month one, two, three) and those metrics should be shared transparently across the team

Seven months of engineering for Localytics produced a feature that, when flipped on, took Snowflake from 5x more expensive to 10x cheaper at Nielsen Marketing Cloud, which became its biggest customer ever

37:07 Explicit transparent monthly targets set expectations and surface problems early

Harry Stebbings · Apr 12, 2024

A great sales hire shows up on day one already prepared — segmented customer lists, identified buyers, drafted emails, marketing collateral — and that preparation is itself the signal of quality.

32:37 Arrives prepared on day one

Ron Gabrisko · Aug 4, 2025

Rep effectiveness should be judged early on pipeline and activity — whether they get the right meetings — and the leader must personally inspect by visiting the territory and watching them with customers

If a rep can only set one or two meetings when you show up for a week in their territory, they're probably not a great salesperson; in front of a customer you can see if they ask good questions and whether the customer wants to buy from them

47:24 Leader must personally visit territory to judge rep effectiveness

Dave Kellogg · Jan 31, 2024

The hardest sales management decision is not firing a rep who isn't selling but keeping one, and you can only make that call if you've listened to their calls and joined them

In territories with no company support or reference customers, any rep would miss quota, so quota attainment alone can't tell you who's doing the right things — only direct exposure to their calls can

32:41 Only direct call listening not quota attainment reveals whether to keep a struggling rep

Brendon Cassidy · Mar 8, 2024

The clearest sign a rep isn't working is that you repeatedly have to take over their calls and they aren't getting better at running them

The bar is whether they can run the call the way you want with you helping only at the margins; most of his failed hires were ones where he had to jump in and fix calls going sideways

22:36 Repeatedly rescuing their calls is the failure signal

Dan Fougere · Nov 22, 2024 · hedged

Most people on a performance improvement plan do not recover, though some do; obvious train wrecks should be exited immediately, while reps with a fixable gap deserve a short, structured chance.

You need a process where the leader tells them what to do, shows them, gives feedback and confirms improvement — if they can't iterate and improve, you have your answer.

45:34 Short structured pip separates fixable from hopeless

Becca Lindquist · May 2, 2026

You can tell within about three weeks whether an individual contributor rep will work out, even though enterprise reps have a nine-month ramp

The early signals are whether they can think critically about a prospect's business (e.g. stack ranking a target account list after boot camp) and their raw activity metrics — if they aren't sending emails and picking up the phone they won't generate pipeline

17:37 Critical thinking plus activity within three weeks