How will AI change the size and structure of sales organizations?

Dave Kellogg · Jan 31, 2024

Battery Ventures argues that supporting 30 quota-carrying sellers will take a 75-person sales organization in future versus 110 today, a roughly 30% cut

63:15 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

Ishan Mukherjee · Apr 4, 2025

Sales teams will become dramatically smaller, potentially 10-20% of current org sizes, as agents raise rep productivity

It is the probable productivity gain path, matching what has happened in engineering and other functions and what he has seen across a career building automation systems and warehouse robots

Scope: framed as a probable path, and a harsh reality

42:37 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

Amit Bendov · Sep 12, 2025 · speculative

There will be far fewer sellers in the future, but each will earn a lot more because they will generate much more.

Individual sellers will be generating far more revenue.

Scope: 'I haven't spent a ton of time thinking about it'

49:10 20VC: Why AI SDRs are BS and Do Not Work | How to Use AI in Your Sales Team and Process to Win Today | What Skills Do All New Reps Need to Have in an AI First World with Amit Bendov, CEO @ Gong

Carles Reina · Apr 11, 2026

AI will shrink future sales teams: the right move is to hire fewer, more concentrated top performers and pay them extremely well rather than doubling or 5x-ing headcount

A 50% productivity improvement means fewer people are needed, and he prefers managing a smaller, very highly compensated team of people performing at a level no one else is

Scope: 50% productivity improvement is his stated goal at ElevenLabs

8:54 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

Harry Stebbings · May 2, 2026

Jason Lemkin has said he got rid of much of his team, including a lot of his sales team, because AI SDR tools let him do better with less

He has AI SDR products like Artisan, Qualified and Monaco covering the work.

50:27 20VC: Inside Clay's Sales Playbook Scaling to $100M ARR | How to Set Sales Comp Plans | How to Read Sales Talent Linkedin Profiles | What Profiles to Hire & Fire | How to Increase Performance and Speed in Sales Teams with Becca Lindquist

Harry Stebbings · May 23, 2026

He would rather have a few expensive full-stack AI-enabled SDRs running end-to-end than ten times as many low-cost, low-quality outbound SDRs

The cheap low-level outbound function is dead; AI lets a smaller number of reps run the whole motion end to end

Scope: Specific salary numbers are illustrative

47:25 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 · Jun 20, 2026

The future of org design is 'super contributors' — cutting headcount to pay a smaller number of AI-leveraged people 10x more, rather than hiring more salespeople.

AI outbound, inbound, pipeline and forecasting tools let one exceptional salesperson do what a team used to, as Zeb at ClickUp argued when cutting staff to pay top performers more.

21:07 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport

Ron Gabrisko · Aug 4, 2025

As long as humans are buying software you need humans to sell software, so Databricks will have more sales reps in five years, not fewer

AI is used to make the org more efficient, but the company intends to go big and will keep hiring

56:15 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

Figma will keep growing its sales headcount rather than pushing for more efficiency, going against the prevailing direction

Supporting half a million customers with roughly 300 quota-carrying reps is already extremely efficient, and the strategic customer work more headcount enables is producing great results

Scope: Shaunt frames this as possibly unique to Figma; Dylan is on board rather than pushing for efficiency

35:29 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

Becca Lindquist · May 2, 2026

AI doesn't replace SDRs, it multiplies their output — an SDR armed with an AI stack can go from ~15 to ~40 meetings a month, so the right response is to grow the SDR team, not shrink it.

More productivity per rep means you should multiply headcount to take all the oxygen out of target accounts.

Scope: meeting numbers given as illustrative thesis, not measured results

54:42 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 19, 2025 · hedged

Jason Lampkin claims that young people fundamentally don't want to work, that AI is already as good as them at sales, marketing and content, and that within twelve months there will be huge unemployment among lower-level tech employees

AI matches entry-level performance in SDR, marketing and social content roles

Scope: attributed to Jason Lemkin, not Harry's own view

17:50 20VC: Duolingo Co-Founder on Why $3M is Harder than $100M to Raise | Why You Should Always Take Tier 1 VCs Even at Worse Terms | Why Europe Can't Win Unless the US Screws Up | How AI Impacts the Future of Work and Education with Severin Hacker

Luke Harries · May 23, 2025

The inbound SDR role can be fully replaced by a conversational AI agent

The real function of an inbound SDR is data collection — BANT screening before booking the AE — which either belongs on the form or can be handled by an AI agent that qualifies faster, and you could even clone the AE's voice so it feels like them prescreening their own deal flow

Scope: applies to inbound SDRs in enterprise sales cycles; concedes the best SDRs are persuasive and friendly

68:08 20VC: ElevenLabs Head of Growth on Why You Do Not Need PMs | The 7-Part Launch Playbook That Gets 700K+ Views Per Product | The Truth About CAC, Payback & Performance Marketing in AI with Luke Harries

Harry Stebbings · Sep 1, 2025

Most junior marketing managers and SDRs will be replaced by agents, not augmented by them

Most 25-26 year olds in those roles are not brilliant, do not love the craft, and will not be better than a phenomenal agent within the next twelve months

Scope: scoped to junior marketing managers and SDRs; timeframe: agents good enough within twelve months

24:43 20VC: Cohere Founder on How Cohere Compete with OpenAI and Anthropic $BNs | Why Counties Should Fund Their Own Models & the Need for Model Sovereignty | How Sam Altman Has Done a Disservice to AI with Nick Frosst

Ishan Mukherjee · Apr 4, 2025

The reps who survive are those building non-transactional, long-term strategic relationships on high-ACV deals, and they will be able to cover two to three times more accounts

The best organizations are already increasing book size per rep — from five customers to seven to twelve over successive years

Scope: endorsing and extending a point he attributes to Jason

43:16 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

Ryan Petersen · Jun 20, 2026 · hedged

AI won't remove the need for large field sales headcount, because sales is a relationships game and there's a hard limit to how many relationships a human can maintain — AI might roughly double the ratio at best.

Global trade requires boots on the ground to interface with every shipping business; Yelp sustains 3,600 salespeople calling on restaurants and prints cash.

Scope: says he is 'somewhat skeptical'; grants AI could double relationships per rep

21:41 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport

Ishan Mukherjee · Apr 4, 2025

The most significant structural change to sales teams will be a rise in quota and book size per rep, leading to fewer, smaller teams and compressed management layers

As humans get more productive and can support more customers, the book size each seller carries fundamentally changes, which changes the whole org structure and requires different kinds of leaders

62:20 Bigger books per rep compress management layers

Chad Peets · May 23, 2026 · speculative

There is a plausible world in which only five or six technology companies really matter, which would sharply reduce the need for salespeople

With only a handful of relevant companies there simply aren't enough vendors to employ a large sales ecosystem

63:08 Vendor consolidation not productivity shrinks the sales profession