How many reps should a company hire in its first sales hires?

Jeanne DeWitt Grosser · Mar 9, 2022

You should hire two to three early reps rather than one

A single individual's read on the pattern can't be trusted; multiple reps corroborate whether you're honing in on an ideal customer profile and seeing replicability, and it avoids mistaking a bad rep for a broken model

Scope: two to three, not ten to twenty

7:22 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

Founders should hire multiple first sellers at the same time, though the point is distilling signal from noise rather than pitting reps against each other

With one rep, results only tell you about that individual; with two, differing results let you separate rep quality from product, messaging and customer signal

17:49 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 · Mar 22, 2023

You should hire two sales reps at the same time, otherwise you can't tell whether a single underperformer is just a bad rep

With only one rep you have no comparison point to know if the failure is the rep or the process

Scope: attributed to Jason Lemkin

10:49 20Sales: The 3 Profiles of a Sales Rep, How to Negotiate in a Sales Process, How to Sell to a CFO & How You Should Shift Sales Messaging in a Downturn with Frank Fillmann, CRO @ Salesforce Australia

Rich Liu · Jun 7, 2023

You should hire sales reps two at a time rather than one

Cohorting helps ramping and creates competitive support, and two data points give minimum viable signal to separate whether failure is the product-market fit and messaging or the rep

Scope: if two great reps you win; if two bad reps you may have to restart

19:48 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

It's better to hire two to three sales reps at a time rather than one, if the company can afford it.

Scope: if you can afford it

0:00 20Sales: Slack, Atlassian, Dropbox: Five of the Biggest Lessons on Starting, Scaling and Managing Sales Teams from 25 Years Leading the Best with Kevin Egan, Global Head of Enterprise Sales at Atlassian

Kevin Egan · Jul 12, 2023

Founders should hire two to three sales reps at the same time rather than one

Comparing reps side by side reveals both whether reps can accelerate at all and which individuals are actually carrying the load

Scope: if you can afford it

13:21 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

You should hire more than one sales rep at a time rather than one

Onboarding is a big time investment that amortizes across more people, and a founding sales group creates collaboration, testing of sales plays, energy and foundational culture

Scope: the value is in scale and team culture, not internal competition

13:43 20Sales: Why The Founder Has To Be The One To Create The Sales Playbook, When To Hire Your First Rep, Why Junior is Better Than Senior, How to Manage Sales Rep Compensation, How To Onboard New Sales Reps and more with Lori Jimenez, CRO @ WorkRamp

Harry Stebbings · Oct 4, 2023

Hiring two reps at once gives a more holistic read on whether poor sales results are a product problem or a people problem

With one rep you can't tell if the product isn't selling or the rep is bad; with two, if one sells and one doesn't you know it's the person, and if both fail it points to the product

19:59 20Sales: Why the Founder Should Not Be the One to Create the Sales Playbook, Why You Should Hire a Sales Leader Before Sales Reps & Why You Should Not Hire Sales Leaders From Big Companies with Matt Rosenberg, CRO @ Grammarly

Chris Degnan · Nov 10, 2023

You should always hire at least two reps into a new territory, because a single person should never be the litmus test for whether that territory works.

With one rep you can't tell whether failure is the territory or the person; with two, a split outcome proves it's behaviour, so you copy what the winner does or cut bait.

41:23 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

Dave Kellogg · Jan 31, 2024

You should hire three reps of the same profile at a time — for the controlled-experiment effect, not for a hunger-games competitive effect

One hire tells you nothing when they fail — maybe an outlier, maybe a clown — and two barely more; three of the same profile gives a real read, so if all three fail you know not to repeat it and if it works you know to go hire six or nine more

Scope: framed as the early-days job being to run good experiments

31:08 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

Julian Teixeira · Mar 7, 2025

You should hire two first sales reps at a time rather than one.

Competition gives them someone to chase, and a sample size of two lets you tell whether failure is systemic or person-specific.

9:20 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

Founders should hire sales reps two at a time, because with a single hire you can't tell if the performance is good, while two make the comparison obvious

With one rep you have no baseline to judge good versus bad; with two, the difference is clear — Heap deliberately hired her and Todd together intending to keep the better one

Scope: framed as advice to founders making early sales hires

34:32 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

Maggie Hott · Dec 14, 2022

Founders should always hire sellers in multiples rather than one at a time — but for onboarding leverage and peer support, not internal competition

Training four sellers costs barely more time than training one because the enablement sessions are identical, and a cohort supports each other, shares ideas and grinds together, as she saw in Slack's early days

Scope: if you can afford to hire multiple people

36:19 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

Matt Rosenberg · Oct 4, 2023

Hiring two early sales reps is right, but the value is collaboration rather than competition — you should not create competition between your first two sales hires

Two reps is too small a sample to draw real conclusions from comparison; early sales is a laboratory where you want scientists collaborating, sharing what worked and marrying the two styles, and a great rep with bad product-market fit won't sell either so the comparison tells you nothing

Scope: applies specifically to the first two sales hires at that early stage

20:18 20Sales: Why the Founder Should Not Be the One to Create the Sales Playbook, Why You Should Hire a Sales Leader Before Sales Reps & Why You Should Not Hire Sales Leaders From Big Companies with Matt Rosenberg, CRO @ Grammarly

Carlos Delatorre · Jan 24, 2025

Reps should be hired in co-located groups rather than as lone rangers, primarily because isolated reps can't get quick help ramping — not mainly because of competition

At MongoDB, analysis of attrition found single reps in a city with no other employees had roughly 4x higher attrition; questions that would take 10 seconds to ask a neighbor require scheduling time, so failure likelihood is far higher

Scope: agrees with Lamkin's conclusion but for a different reason — mutual help over competition

14:12 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

Mark Goldberger · Apr 19, 2023

In the early days you should hire the single best available seller when you find them rather than wait to hire two at once; batch hiring only makes sense at scale

Sellers who deliver 10x rather than 1-1.5x growth are rare, and finding and recruiting two such people simultaneously is exceptionally unlikely; early on each additional player has outsized impact

10:20 Hire one great seller opportunistically