Jason Lemkin (SaaStr)01 January 2026

We replaced our sales team with 20 AI agents—here’s what happened

7Frameworks

15Insights

Episode overview

Jason Lemkin explains how SaaStr moved from roughly eight to ten go-to-market employees to one full-time account executive, 20% of a chief AI officer, and about 20 agents while maintaining similar productivity. He argues that email-based prospecting and inbound qualification are likely to be heavily automated, while strong salespeople and leaders who can deploy, train, and supervise agents should become more valuable. The conversation emphasizes that these systems require high-quality source material, daily correction, careful customer segmentation, and hands-on vendor support rather than autonomous, out-of-the-box deployment.

Key ideas

SaaStr reports approximately the same go-to-market productivity from 1.2 humans and 20 agents as it previously received from roughly eight to ten people.
Email-based SDR work and human qualification of inbound leads are the sales functions Lemkin expects AI to displace first.
Agent quality comes from training on the strongest salesperson’s copy and process, then continuously reviewing, correcting, and testing outputs.
Buyers should prioritize vendors that provide strong hands-on deployment help because even capable agent software can fail without onboarding and training.
Managing multiple agents is substantial ongoing work: they operate continuously, require segmentation to avoid conflicts, and still need human oversight.
Sales leaders should personally deploy an agent, while junior salespeople should become expert users of whatever AI systems their organization adopts.
High-value, bespoke enterprise selling and in-person relationship work remain more defensible than high-volume digital outreach.
Lemkin expects fewer routine sales roles but potentially more highly paid professionals who orchestrate multiple agents and deliver far more revenue per person.

Transcript available · source text is retained privately and is not published

Frameworks in this episode

Sales4 steps

Best-Rep Email Cloning

Feed the agent your single best rep's best email, then let it AB-test variants—that's how AI beats your mid-pack.

Read →

Sales4 steps

The 30-Day Agent Training Loop

Ingest your docs, then correct the agent an hour a day for 30 days until it performs like your best rep.

Read →

Entrepreneurship4 steps

The Chief Agentic GTM Officer Play

Pick one painful problem, one leading vendor, and deploy an agent yourself—50 hours later you're hyper-employable.

Read →

Sales4 steps

The Forward-Deployed Engineer Vendor Column

Don't buy AI GTM tools on features—buy on who will actually get on the phone and deploy it with you.

Read →

Sales4 steps

The GTM Agent Deployment Sequence

Roll out AI sales agents in the order of lowest effort and highest ROI: start with support, end with reactivation.

Read →

Strategy4 steps

The Incognito Cry Test

Go through your own product as an anonymous customer, find what makes you cry, and buy an agent to fix that.

Read →

Sales4 steps

The Lead-Rich Audit

You don't need SaaStr's scale—count your website visitors and untouched CRM leads to see you're already lead-rich.

Read →

People & resources mentioned

Attributed to the moment in the episode. Timestamps are approximate.

People · 14

Jason LemkinMentionsJason created and runs SaaStr and previously co-founded and led EchoSign before its acquisition by Adobe.
“Today, my guest is Jason Lmin, founder and CEO of Saster, the world's largest community for B2B founders”
▶ Watch at ~1:00approx.
Jason LemkinCoinedJason created and runs SaaStr and previously co-founded and led EchoSign before its acquisition by Adobe.
“I am a two-time founder who started writing a blog, my god, in 2012”
▶ Watch at ~5:30approx.
AmeliaMentionsour chief a officer who who runs everything
“Amelia who's our chief a officer who who runs everything. She spends 20% of her time managing the agents, orchestrating the agents.”
▶ Watch at ~12:30approx.
MaggieMentionswho's in the leadership of OpenAI
“We with with Maggie who's in the leadership of OpenAI. She said they just can't hire enough enterprise reps now.”
▶ Watch at ~13:00approx.
Mark BenioffMentionsFormer co-CEO of Salesforce alongside Bret Taylor and a proponent of Agentforce.
“we're pretty far on agent force, which is Salesforce's one, which Mark talks a lot about”
▶ Watch at ~27:30approx.
Brian HalliganCoinedToday my guest is Brian Hallagan, co-founder and longtime CEO of HubSpot.
“Brian Halligan, who's the founder chairman of HubSpot, did one too.”
▶ Watch at ~30:00approx.
Sam BlondMentionsJason Lemkin’s first SDR, later CRO at Brex and a partner at Founders Fund.
“Sam Blonde was one of our sales leaders. Then he became CRO of Brex and others.”
▶ Watch at ~44:30approx.
Jen AbelMentionsToday, my guest is Jen Ael, co-founder of Jellyfish, where she and her team help earlystage founders learn how to sell
“This came up when we had Jen Ael on the podcast.”
▶ Watch at ~47:30approx.
Kyle NortonMentionsmentioned
“He's got 100 folks on the sales team. Kyle does. With AI, he's trying he's targeting 3 to five million in revenue per rep.”
▶ Watch at ~1:00:30approx.
Elena VernaMentionsElena Vernon who's been on the podcast is just like a huge proponent of everyone will be product LED self-serve eventually
“I just had the head of a growth from lovable Elena Ver on the podcast.”
▶ Watch at ~1:31:00approx.
Ben ChestnutRecommendsmentioned
“watch the one I did with Ben Chestnut um right after they got acquired”
▶ Watch at ~1:38:30approx.
Matt PlankRecommendsmentioned
“Matt Planku of Rippling did one with Sam Blonde who was NCR of Brex. It's called Rippling Secrets to Hyperrowth.”
▶ Watch at ~1:39:30approx.
Matt MacInnisMentionsour rco Matt McGinnis who you know joined the company about a year before I did you know he has been the one
“I just uh had Matt McInness on the podcast. Former COO, now CPO Y at Ripling.”
▶ Watch at ~1:40:00approx.
Lenny RachitskyMentionstoday we've got another very special compilation episode something I've been pulling on more and more with the podcast and the newsletter
“All right, Lenny, you're the best. I'm I'm I'm just a super fan. I'm lucky to be here.”
▶ Watch at ~1:40:30approx.

Resources · 58

Product PassMentionsproduct · Lenny Rachitsky
“Head on over to lenny'snewsletter.com and click product pass.”
▶ Watch at ~2:30approx.
DXMentionssoftware · DX
“DX, the developer intelligence platform designed by leading researchers.”
▶ Watch at ~2:30approx.
Lenny's NewsletterMentionsnewsletter · Lenny Rachitsky
“Head on over to lenny'snewsletter.com and click product pass.”
▶ Watch at ~2:30approx.
v0Mentionssoftware · Vercel
“Vzero is the web development assistant designed for professionals of all technical backgrounds.”
▶ Watch at ~3:30approx.
VercelMentionscompany · Guillermo Rauch
“Visit verscell.com/lenny to get started.”
▶ Watch at ~4:00approx.
AdobeMentionscompany
“after I sold my startup to Adobe.”
▶ Watch at ~5:30approx.
SaaStrCoinedcompany · Jason Lemkin
“We started doing a couple meetups. You've done meetups. Um, before anyone did this stuff, we did a big meetup in 2015.”
▶ Watch at ~6:00approx.
SaaStr AnnualMentionsevent · SaaStr
“Then we do 10,000 people a year at Saster Annual.”
▶ Watch at ~6:00approx.
Lenny's NewsletterCoinednewsletter · Lenny Rachitsky
“How many as how many of those is a human willing to reach out to”
▶ Watch at ~11:00approx.
LinearMentionssoftware · Linear
“The ones that don't really understand what linear does.”
▶ Watch at ~13:00approx.
OpenAIMentionscompany
“Maggie who's in the leadership of OpenAI. She said they just can't hire enough enterprise reps now.”
▶ Watch at ~13:00approx.
VercelMentionscompany · Guillermo Rauch
“if you go to Verscell, if you go to Replet, if you go to they're all going to tell you the same.”
▶ Watch at ~13:00approx.
ElevenLabsMentionscompany · ElevenLabs
“Why is 11 Labs out doing a road show, right? It works.”
▶ Watch at ~14:30approx.
LovableMentionssoftware · Lovable
“Bolt is probably a distant number three behind Rep and Lovable, right?”
▶ Watch at ~15:30approx.
BoltMentionssoftware · StackBlitz
“Bolt is probably a distant number three behind Rep and Lovable, right?”
▶ Watch at ~15:30approx.
HarveyMentionssoftware · Harvey AI
“It's not one law firm looking at Harvey. It's everyone.”
▶ Watch at ~17:30approx.
LegoraMentionssoftware
“why are Harvey and the others in Lagora doing so?”
▶ Watch at ~18:30approx.
AgentforceRecommendssoftware · Salesforce
“pick uh agent force pick qualified pick artisan pick whatever you want”
▶ Watch at ~27:00approx.
QualifiedRecommendssoftware
“pick uh agent force pick qualified pick artisan pick whatever you want”
▶ Watch at ~27:00approx.
NotionMentionssoftware · Notion Labs
“It's the same idea of building your own notion. You could do it, but don't do it.”
▶ Watch at ~29:00approx.
ReplitUsessoftware · Replit
“I built a lot of stuff in Replet. We can talk about it for fun. I'm like a top 1% user.”
▶ Watch at ~29:00approx.
HubSpotCoinedcompany · HubSpot
“Brian Halligan, who's the founder chairman of HubSpot, did one too.”
▶ Watch at ~30:00approx.
SierraMentionscompany · Bret Taylor and Clay Bavor
“you don't have to buy Sierra and you don't have to buy decacon necessarily”
▶ Watch at ~32:00approx.
FinMentionsproduct · Intercom
“you don't have to buy Finn but one potential place to start is is your support”
▶ Watch at ~32:30approx.
ArtisanUsessoftware
“we picked a YC company called Artisan.”
▶ Watch at ~33:00approx.
QualifiedUsessoftware
“we used this vendor called Qualified, which was founded by the XMO of Salesforce”
▶ Watch at ~34:00approx.
SaaStr AnnualUsesevent · SaaStr
“if you go to sasterannual.com and anyone should buy a product like this”
▶ Watch at ~34:30approx.
ArtisanMentionssoftware
“Artisan and Qualified just did the work with us.”
▶ Watch at ~36:00approx.
SalesforceUsescompany · Salesforce
“we did agent force really early with Salesforce”
▶ Watch at ~38:00approx.
AgentforceUsessoftware · Salesforce
“we did agent force really early with Salesforce”
▶ Watch at ~38:00approx.
BrexMentionscompany
“Sam Blonde was one of our sales leaders. Then he became CRO of Brex and others.”
▶ Watch at ~44:30approx.
GongMentionssoftware · Gong
“they use a to an automation tool whether it's Outreach or Gong or Salesoft or Mixmax”
▶ Watch at ~47:00approx.
OutreachMentionssoftware
“they use a to an automation tool whether it's Outreach or Gong or Salesoft or Mixmax”
▶ Watch at ~47:00approx.
SalesloftMentionssoftware
“they use a to an automation tool whether it's Outreach or Gong or Salesoft or Mixmax”
▶ Watch at ~47:00approx.
MixmaxMentionssoftware
“they use a to an automation tool whether it's Outreach or Gong or Salesoft or Mixmax”
▶ Watch at ~47:00approx.
EppoMentionssoftware · Eppo
“now home to EPO, the leading experimentation and feature flagging platform.”
▶ Watch at ~57:00approx.
DatadogMentionscompany · Datadog
“This episode is brought to you by Data Dog, now home to EPO, the leading experimentation and feature flagging platform.”
▶ Watch at ~57:00approx.
AirbnbMentionscompany · Brian Chesky, Joe Gebbia, and Nathan Blecharczyk
“the same team that built experimentation at Airbnb built EPO.”
▶ Watch at ~58:00approx.
ClayMentionssoftware · Clay
“even clay I think starts at 100k a year”
▶ Watch at ~59:00approx.
Owner.comMentionscompany
“There's a company I'm on the board of called owner.com which is kind of like AI for restaurants”
▶ Watch at ~1:00:00approx.
MomentumUsessoftware
“There's two we use. One's called Momentum, one's called Attention. They're both great.”
▶ Watch at ~1:01:00approx.
AttentionUsessoftware
“There's two we use. One's called Momentum, one's called Attention. They're both great.”
▶ Watch at ~1:01:00approx.
GranolaMentionssoftware · Granola
“granola is, you know, a side example for everything.”
▶ Watch at ~1:01:30approx.
PalantirMentionscompany · Peter Thiel, Alex Karp, Stephen Cohen, Joe Lonsdale, and Nathan Gettings
“Palunteer is obviously the single most successful public B2B company at the moment”
▶ Watch at ~1:05:30approx.
RipplingMentionscompany · Parker Conrad
“We had multip of the heads of uh revenue at um Ripling Speak at Saster”
▶ Watch at ~1:12:30approx.
LennybotRecommendswebsite · Lenny Rachitsky
“If you don't believe me, folks, go to Lennybot.”
▶ Watch at ~1:14:00approx.
ChatGPTMentionssoftware · OpenAI
“Our best who are our best therapists today as we record this chat. GPT is our best best therapist on planet Earth.”
▶ Watch at ~1:14:30approx.
ReplitRecommendssoftware · Replit
“go fire up your browser. Do it in incognito. Go to your app and do everything with a fresh Gmail address.”
▶ Watch at ~1:25:30approx.
SalesforceMentionscompany · Salesforce
“Salesforce has become the database for all these so so that's a little hint of the plurabus hive mine”
▶ Watch at ~1:32:30approx.
ReveRecommendssoftware
“There is an app called Reeve. It used to be Reevar. It's for imaging”
▶ Watch at ~1:33:30approx.
CanvaMentionscompany · Melanie Perkins, Cliff Obrecht, and Cameron Adams
“That stuff that we used to torture, we used to fire up Canva and try to create things”
▶ Watch at ~1:34:00approx.link ↗
ReveUsessoftware
“I use it two or three times a day and I use all this stuff.”
▶ Watch at ~1:35:00approx.
Everything That Breaks on the Way to One BillionRecommendsother · SaaStr
“It's called Everything That Breaks on the Way to One Billion.”
▶ Watch at ~1:38:30approx.
Rippling’s Secrets to HypergrowthRecommendsother · SaaStr
“It's called Rippling Secrets to Hyperrowth. It sounds like a commercial for Rippling”
▶ Watch at ~1:39:30approx.
Lenny's PodcastCoinedpodcast · Lenny Rachitsky
“All right, Lenny, you're the best. I'm I'm I'm just a super fan. I'm lucky to be here.”
▶ Watch at ~1:40:30approx.
SaaStrMentionscompany · Jason Lemkin
“we have two websites, saster.com and SASI. Just go to saster.ai”
▶ Watch at ~1:40:30approx.
SaaStr AIRecommendswebsite · SaaStr
“Just go to saster.ai, and just play with the tools we built.”
▶ Watch at ~1:41:00approx.
Lenny's PodcastMentionspodcast · Lenny Rachitsky
“You can find all past episodes or learn more about the show at lennispodcast.com.”
▶ Watch at ~1:42:00approx.

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Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Myth Buster· 2

Myth Buster36:30

You Don't Need SaaStr-Scale Data To Make Agents Work

A common excuse Lemkin hears is 'SaaStr has scale, we're too small.' He pushes back: even a company with 300 customers has ~30,000 website visitors and tens of thousands of leads in its CRM that no human is contacting. You need a bit of scale and traffic, not millions of names. The same holds for training data — a couple of months of really good content plus a long tail beats a 12-year archive.

You don't need millions of names — a bit of scale and traffic is enough
300 customers usually means ~30k visitors and tens of thousands of untouched CRM leads
Vendors sometimes tell prospects they have 'too much data' — that's wrong
Deep training history matters less than expected; a couple months of good content suffices

“You don't need the scale of numbers that you and I have to make these agents work.”
Jason Lemkin · 37:00

“I thought having 12 years of content made the difference. Nah.”
Jason Lemkin · 37:30

#ai-agents#data#myth-buster#small-business

Myth Buster44:30

Nobody Cares If the Email Is From AI — And Human Emails Aren't Better

After sending hundreds of thousands of emails, SaaStr found it doesn't matter whether you disclose the sender is AI — they've tried disclosing, faking, and just sending, and now they just send it. People don't care as long as the email adds value and gets an instant response. Lemkin reinforces this with the story of inheriting Adobe reps whose emails were the worst his sales leader had ever read: AI clears that bar easily.

They tested disclosing vs faking vs just sending — now they just send it
People don't mind AI as long as the email adds value and responds instantly
Founders often reply 'I can tell this is AI but it's pretty good, can we meet?'
Human reps' emails are often far worse than people assume

“These are the worst emails that I've ever read.”
Jason Lemkin · 45:00

“We We just send it and no one cares.”
Jason Lemkin · 45:30

#outbound#email#ai-agents#myth-buster

Hot Take· 5

Hot Take13:00

AI Is Displacing the Midpack and the Mediocre, Not the Best

Lemkin argues AI isn't replacing top salespeople — it's taking the jobs people don't want to do and displacing the mid-tier and below. He'd happily hire two more great humans tomorrow, but won't hire a rep who still doesn't understand the product after three months. The best humans get superpowers from AI; he's not convinced the rest do.

AI takes the jobs people don't want to do and displaces the midpack and mediocre
The reps who don't understand what the product does are the ones at risk
Great enterprise reps are still in huge demand — OpenAI 'can't hire enough'
The best get superpowers from AI; the rest may not

“AI is replacing the jobs people don't want to do today and it is displacing the media the midpack and the mediocre.”
Jason Lemkin · 13:30

#ai-agents#sales#careers#hot-take

Hot Take14:00

The Plays Still Work — It's the Playbooks That Are Broken

Lemkin's frame for GTM in the AI age: outbound, webinars, podcasts, events all still work. What's broken is the old playbooks. For companies not riding AI demand, growth has decelerated so much that nothing seems to work; for the ones blowing up, the plays work but are run from a hyper-PLG posture where the job is choosing which of too many leads to answer.

All the plays (outbound, webinars, podcasts, events) still work
The playbooks are broken — old-school SaaS plays lack the ROI they had in 2021
Hypergrowth AI companies have so many leads that half the job is picking which to respond to
The market is wildly bifurcated: low-end price increases vs high-end demand explosion

“All the plays work. It's the playbooks that are kind of broken in the age of AI.”
Jason Lemkin · 14:00

#go-to-market#sales#ai#strategy

Hot Take19:30

The Email SDR Will Be 90% Displaced by AI Next Year

Lemkin's prediction for the sales profession: the classic email-cadence SDR and the human who qualifies inbound leads will be mostly extinct within a year. AI already qualifies everyone on the website invisibly and books the meeting — there's no reason to make a prospect wait two days for a 21-year-old who doesn't know the product. Door-knocking SDRs survive; the AE's job is ~70% safe next year but declines toward 40–50%.

Email-based cadence SDRs will be ~90% displaced by AI next year
Human inbound qualifiers should be 'extinct next year' — it's a bad customer experience anyway
Door-to-door SDRs are not displaced
AE jobs ~70% safe by end of next year, declining to 40–50% over time

“The emailbased cadence SDR will be 90% displaced by AI next year.”
Jason Lemkin · 19:30

“They should be extinct next year.”
Jason Lemkin · 20:00

#sdr#sales#careers#ai#predictions

Hot Take28:30

Don't Build Your Own GTM Agents — Buy Them (Unless You're Vercel)

Lemkin is a self-described top-1% Replit user who built many apps himself, but none of SaaStr's GTM agents were built in-house. His argument: it's the same reasoning as building your own Notion — you could, but you shouldn't, because these products aren't that expensive and the pace of innovation means anything you build internally goes obsolete in a couple of months unless you have a dedicated, eager engineer.

None of the GTM stuff was built in-house — buy, don't build
Same logic as building your own Notion: you could, but don't
The products aren't that expensive relative to a human
In-house builds go obsolete in months because the pace of innovation is so fast

“None of the GTM stuff we built ourselves. Don't build it yourself. You're not Versel.”
Jason Lemkin · 28:30

#build-vs-buy#ai-agents#go-to-market#hot-take

Hot Take1:15:00

AI Has Raised the Bar: Deliver ROI Before the Contract Is Signed

Lemkin frames this as maybe the biggest change of all. The old B2B model was to avoid pilots, minimize them, then roll out over years — almost rip off the customer to get the deal. AI has flipped customer expectations: the winners blowing up are the ones delivering ROI before the document is e-signed. Companies still playing the old games are the public companies growing 8%.

Old model: avoid pilots, then roll out slowly over years
AI has raised what customers expect — go live and get value before you pay
Salesforce's Benioff envies Palantir's ability to make customers live before paying
Companies clinging to the old games are the ones growing ~8%

“I wish every Salesforce customer now could go live before they pay”
Jason Lemkin · 1:15:30

“you've got to deliver the ROI before the document is e- signed today.”
Jason Lemkin · 1:16:00

#sales#roi#pilots#ai#hot-take

Explainer· 2

Explainer17:30

Why AI Startups Are Blowing Up: Everyone's In-Market At Once

Lemkin explains that the traditional B2B assumption was that only 3–5% of prospects are in-market to buy in any given year. With AI, that has flipped — in many categories more than 50% are in-market at once, because there's top-down pressure to adopt AI everywhere. It's not one law firm evaluating Harvey; it's everyone. He warns this is a bubble-like window that will eventually revert.

Traditionally only 3–5% of prospects are in-market in a given year
For high-ROI AI products, it's now north of 50% in-market at once
The demand is driven by top-down 'we need to adopt AI' pressure across whole categories
This artificial window will end and revert to more old-school patterns

“the traditional metric was in most categories, 3 to 5% of prospects would be in market a year.”
Jason Lemkin · 17:30

“In many categories, we're north of 50% in market.”
Jason Lemkin · 18:00

#ai#demand#market-timing#b2b

Explainer54:00

Who Should Orchestrate Your Agents: Promote a Data Nerd, Not a Salesperson

Lemkin doesn't believe the 'GTM engineer' hire exists yet — instead, promote someone internally who is quant, loves data, and will sit in front of it for a couple hours a day. They can come from product, marketing, or RevOps, but almost never from regular sales. The key point people misunderstand: agents operate autonomously but require constant oversight and iteration — buy one and disappear and you get zero ROI.

Promote internally — the role is best filled by a quant 'nerd', not hired off LinkedIn
Candidates come from product, marketing, or RevOps; odds from regular sales are ~zero
Agents operate autonomously but need constant oversight and iteration
Buy a product and disappear and you'll get zero ROI

“It's got to be a nerd, someone that likes marketing and sales and is quant.”
Jason Lemkin · 54:00

“Odds they come out of regular sales approach zero.”
Jason Lemkin · 54:30

#orchestration#ai-agents#hiring#revops

Story· 1

Story07:00

How SaaStr Went From 10 Sales Humans to 1.2 Humans + 20 Agents

After two paid, high-end sales reps quit on-site at SaaStr's 10,000-person event, Jason Lemkin decided to stop hiring humans in sales entirely and push the limits with AI agents. He now runs the go-to-market org with 1.2 humans (one AE plus 20% of a chief AI officer) and 20 agents, doing roughly the same business he did with ~10 people. His verdict: net productivity is about the same, but it's far more efficient because software scales.

Two high-paid reps quit on-site at the annual event; it was the eighth sales team he'd built
A horizontal 'general' agent (Deli / digital Jason) had already closed a $70k sponsorship on its own
Now ~1.2 humans + 20 agents does about what 10 human GTM people did
Net productivity is roughly the same, not better or worse — the win is efficiency and scale

“We're done with hiring humans in sales. We're done.”
Jason Lemkin · 07:30

“The pro the net productivity is about the same. It's not better. It's not worse.”
Jason Lemkin · 09:00

#ai-agents#sales#go-to-market#saastr#automation

Tool· 1

Tool1:33:30

Jason's Cheat-Code Tool: Reve for B2B Marketing Images

In the lightning round, Lemkin recommends an image app called Reve (formerly Reeve/Reevar, at app.reve.com) whose team built their own image LLM. He uses it two or three times a day for the 'boring B2B stuff' — thumbnails, article images — and finds nothing better for that use case, replacing the old workflow of firing up Canva or waiting days for a designer.

Reve (formerly Reeve/Reevar) is at app.reve.com; the team built their own image LLM
Best-in-class for boring B2B marketing images, thumbnails, and article art
Lemkin uses it two or three times a day
Replaces the old Canva-or-wait-four-days-for-a-designer workflow

“There is an app called Reeve. It used to be Reevar.”
Jason Lemkin · 1:33:30

“it's just a simple prompt. Go to it, type in whatever image you want to make.”
Jason Lemkin · 1:34:00

#tools#image-generation#marketing#recommendation

Takeaway· 4

Takeaway23:30

Want To Be Hyper-Employable? Pick One Agent and Train It Yourself

Lemkin's advice for anyone worried about their job: pick one agentic tool for your most painful problem, pick a leading vendor, and personally do the ingestion, training, QA, and daily corrections for ~30 days. Almost nobody does this — most people stay panicked — so the ones who actually get an agent live into production become hyper-employable and could be hired as a 'chief agentic GTM officer.'

Pick one tool for your most acute problem and a leading vendor that treats you well
Do it yourself: ingest the data, train it, QA it, correct mistakes for ~30 days
By day 30 of an hour or two of daily correction, the agent is 'pretty good'
Almost nobody does the work — doing it makes you hyper-employable

“Pick a tool, an agent, an agentic tool to solve one of your problems.”
Jason Lemkin · 23:30

“If you can go do this and get it live into production, you're hyper employable.”
Jason Lemkin · 27:00

#careers#ai-agents#upskilling#advice

Takeaway33:00

Pick the Vendor That Will Actually Help You Deploy, Not the Best Features

SaaStr's success with Artisan and Qualified came down to one thing: those vendors offered to help the most. Because these agents take a month to train, the world's best software with no deployment help is not what most buyers should choose. Lemkin says to add a new column to your evaluation matrix — the forward-deployed engineer — and get on the phone before writing a check to confirm they'll really do the deployment.

The deciding factor for the first two agents was 'they offered to help the most'
Best software with no training help is wrong for 99% of buyers
Add a 'who will help me' column (forward-deployed engineer / SE) to your vendor matrix
The best vendors even turn away business they don't think they can make successful

“But the key to the first two and and if you're going to pick an agent is they they offered to help the most.”
Jason Lemkin · 35:00

“before you write a check get on the phone with Lenny and see if Lenny's really going to do deployment”
Jason Lemkin · 36:00

#vendor-selection#ai-agents#forward-deployed-engineer#sales

Takeaway42:30

The Trick To Good AI Outbound: Train It On Your Best Person's Emails

Lemkin's two biggest learnings on email quality: take your best salesperson or marketer's email copy and use it as the template for the AI, then let the agent A/B test and generate variants from it. The 2024 failures came from launching before Claude 4 and from vendors lying that you could just 'turn it on.' If you're getting terrible AI emails, that's a poorly trained product from a bad vendor.

Use your best person's email copy as the AI's template, then let it A/B test variants
Agents are good at creating variants — ask Claude for three versions of your best email
2024 failures were pre-Claude-4 and from vendors claiming no training was needed
Terrible AI emails = poorly trained product from a bad vendor

“take your best person on your sales team, the best marketer you have, take their email copy and use that as a template for your…”
Jason Lemkin · 42:30

“If you're getting terrible emails, it's a poorly trained product from a bad vendor.”
Jason Lemkin · 44:00

#outbound#email#ai-agents#training#sales

Takeaway1:25:30

The Incognito Test: Buy Your Own Product With a Fresh Gmail

Lemkin's actionable advice for anyone who doesn't feel the excitement: over the holidays, open an incognito browser, use a fresh Gmail, and go through your own product end to end — try support, contact sales, sign up for the newsletter. You'll cry at how bad your support is and how long sales takes to respond. Pick the thing that makes you cry the most and go buy an agent to fix it.

Use incognito + a fresh Gmail to experience your own product as a new customer
Try support, contact sales, and signup flows end to end
You'll be shocked by bad support and slow sales response
Pick the worst experience and buy an agent to fix it — do this quarterly

“Do it in incognito. Go to your app and do everything with a fresh Gmail address.”
Jason Lemkin · 1:25:30

“Pick the thing that makes you cry the most over your mold wine and go buy that agent and fix it.”
Jason Lemkin · 1:26:00

#customer-experience#advice#ai-agents#support

Key ideas

Frameworks in this episode

Best-Rep Email Cloning

The 30-Day Agent Training Loop

The Chief Agentic GTM Officer Play

The Forward-Deployed Engineer Vendor Column

The GTM Agent Deployment Sequence

The Incognito Cry Test

The Lead-Rich Audit

People & resources mentioned

People · 14

Resources · 58

Insights & moments

⚡Myth Buster· 2

You Don't Need SaaStr-Scale Data To Make Agents Work

Nobody Cares If the Email Is From AI — And Human Emails Aren't Better

◆Hot Take· 5

AI Is Displacing the Midpack and the Mediocre, Not the Best

The Plays Still Work — It's the Playbooks That Are Broken

The Email SDR Will Be 90% Displaced by AI Next Year

Don't Build Your Own GTM Agents — Buy Them (Unless You're Vercel)

AI Has Raised the Bar: Deliver ROI Before the Contract Is Signed

✶Explainer· 2

Why AI Startups Are Blowing Up: Everyone's In-Market At Once

Who Should Orchestrate Your Agents: Promote a Data Nerd, Not a Salesperson

❝Story· 1

How SaaStr Went From 10 Sales Humans to 1.2 Humans + 20 Agents

✦Tool· 1

Jason's Cheat-Code Tool: Reve for B2B Marketing Images

▲Takeaway· 4

Want To Be Hyper-Employable? Pick One Agent and Train It Yourself

Pick the Vendor That Will Actually Help You Deploy, Not the Best Features

The Trick To Good AI Outbound: Train It On Your Best Person's Emails

The Incognito Test: Buy Your Own Product With a Fresh Gmail

Myth Buster· 2

Hot Take· 5

Explainer· 2

Story· 1

Tool· 1

Takeaway· 4