Podcast Summary

Lenny’s Podcast: Product | Career | Growth

Episode: We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr)
Host: Lenny Rachitsky
Guest: Jason Lemkin, CEO and Founder of SaaStr
Date: January 1, 2026

Episode Overview

This episode dives deep into how SaaStr, under Jason Lemkin’s leadership, replaced almost its entire sales and go-to-market team with AI agents. The conversation explores the operational, strategic, and cultural shifts necessary to make the transition, the realities of deploying AI in sales, and the implications for the future of sales careers and organizations. Lenny and Jason also share practical advice for sales leaders, founders, and individual contributors seeking to adapt and thrive in this rapidly-evolving AI-driven landscape.

Key Discussion Points & Insights

1. The Shift from Human to AI Sales Teams

SaaStr moved from around 10 full-time salespeople to 1.2 humans (one full-time AE, part-time Chief of AI) and 20 AI agents.
Each former human’s desk is now labeled with the agent’s name (e.g., Reply, Quality, Arty).
Agents work 24/7—including nights, weekends, and holidays.

“We have 10 desks that used to be go to market people. They're all just labeled with our agents... Agents work all night and they work weekends and they work on Christmas.”
— Jason Lemkin (00:04)

SaaStr's business performance is roughly the same with AI agents as it was with its fully-human team, but operations are more efficient and scalable.
The biggest AI impact: replacing the “mid-pack” and mediocre roles that are transactional or repetitive.

“AI is replacing the jobs people don't want to do today and it is displacing the mid pack and the mediocre.”
— Jason Lemkin (00:22, 13:02)

2. How AI Agents Work at SaaStr

AI agents handle:
- Outbound prospecting (sending emails, cold outreach)
- Inbound qualification and lead handling
- Re-engaging lapsed customers
- Customer support (answering event questions, handling refunds, etc.)
AI agents must be trained using the best scripts, best people, and high-quality data; they do NOT work “out of the box.”
- Training involves ingesting data, iterating, and human oversight.

“It takes time to train these agents. They don't work out of the box, but when you dial them in, when you take your best person or your best script and you train an agent with your best person and best script, that agent can start to become a version of your best salesperson.”
— Jason Lemkin (09:41)

Vendors matter: Choose those that will “do the work with you”, not just sell you software.

3. The Future of Sales & Go-to-Market Roles

SDRs/BDRs (Sales/Business Development Reps):
- Entry-level, email-based, and qualifying SDR roles will be “90% displaced by AI next year.”
- In-person, higher-touch sales may remain, but classic inbound/outbound email roles will shrink dramatically.

“The classic SDR junior kid that is hired out of college to send emails … we don't need them… They should be extinct next year.”
— Jason Lemkin (19:27)

Account Executives (AEs):
- The best will gain “superpowers from AI” and become more productive.
- A growing role for “agent orchestrators” who manage multiple AI agents.
Orchestration/Oversight:
- A new, critical role has emerged: someone must oversee and “QA” agents, manage data segmentations, and ensure agents don’t generate conflicts or errors.
- Typically, this is a technical, nerdy marketer, product manager, or ops person (not a classical salesperson).

“It is so much time now to manage these 20. This is interesting. We can't, I don't know when we're going to do the 21st. We may be full.... the agents never sleep, right? So it is so much time now to manage these 20.“
— Jason Lemkin (39:35)

4. Advice for Salespeople & Leaders (Career Tactics)

For Sales Leaders:
Learn to deploy, train, and iterate with AI agents yourself. Don’t delegate; become hands-on. This makes you “hyper employable.”
For Junior Salespeople:
Embrace the tools your company adopts. Become the best at working with agents and accept the new level of productivity and transparency.
For Founders/Startups:
Don’t build GTM AI tools yourself unless you have world-class technical resources. Instead, pick vendors who will act as “forward deployed engineers” and guide you through successful implementation.

“If you can go do this and get it live into production, you're hyper employable.”
— Jason Lemkin (26:02)

5. Best Practices—Making AI Sales Actually Work

Successful AI-driven playbooks:
- Use your BEST reps’ emails as templates for AI; don’t let mediocre or lazy humans define your AI training.
- Constantly QA and iterate. AI will go off-track if not closely managed.
- Segment your CRM/leads so agents don’t overlap or create chaos.
- Choose software partners based on their willingness to roll up their sleeves and help you train and launch—not just features.

“Take your best person on your sales team, your best marketer you have ... use that as the template for your AI.”
— Jason Lemkin (42:33)

Quality Management:
Many bad AI outbound emails are the result of poor training or lazy implementation. A well-trained agent, using your best human’s approach, is “pretty good—and for many teams, better than their average rep.”

6. What Stays the Same vs. What Changes

What’s Changed:

24/7 productivity; instant and scalable outbound/inbound sales.
Entry-level sales paths are vanishing—no more “college grad SDR” pipelines.
Expectations for customer response times and qualification have risen dramatically.

What’s the Same:

The core sales “plays” (events, webinars, outbound, relationships) all still work.
High-touch, high-value, highly personalized sales (e.g., large enterprise deals) are still human-driven.

“All the plays work. It's the playbooks that are kind of broken in the age of AI, all the plays work.”
— Jason Lemkin (14:30)

7. The “Agent Orchestrator” Role

This is the new secret weapon—a highly technical, data-driven operator who manages, segments, and improves the fleet of AI sales agents.
Usually comes from a product, marketing, or ops background (rarely sales).

“This is critical. And ... the chief orchestrator officer ... is a new skill set... you have to grow this resource at home today.”
— Jason Lemkin (54:02)

8. What to Watch Out For / Future Predictions

Organizations will still hire more salespeople net-net, but only the best/hyper-productive; AI “raises the bar.”
Agents are exhausting to manage—don’t underestimate the QA and oversight need.
The next few years may see agent and orchestration “max out”—organizations will hit the limit of how many agents they can handle operationally.

Notable Quotes & Memorable Moments

On Replacing People with AI:
- “We are going to push the limits with agents. We're going to put—even if it doesn't quite work.”
  — Jason Lemkin (08:19)
On The Risks for Sales Professionals:
- “If you can go do this, you're hyper employable.”
  — Jason Lemkin (26:02)
- “AI can be people people, too.”
  — Jason Lemkin (74:12)
On Quality & Training:
- “Agents are really good at AB testing. They're really good at creating variants ... But you just haven't seen a well trained agent.”
  — Jason Lemkin (43:33)
On The Opportunity:
- “If you have those skills. Even though we're not going to need these SDRs ... there is so the amount of revenue and growth in AI leaders is so phenomenal ... you may become more valuable, have a better experience in DTM and ... be better paid.”
  — Jason Lemkin (77:21)
On Staying Honest With Teams About Change:
- “Be honest about it. Be honest that for the best people, it will make them more productive. For the best people ... they will be better at their job. And if it is a threat to some of the folks on the team, the future is coming anyway. We might as well embrace it.”
  — Jason Lemkin (87:32)

Key Timestamps

00:00 – 03:00: SaaStr’s transition to 20 AI agents, what that looks like day-to-day
05:45 – 09:00: How SaaStr became a community, monetized with sponsorships/tickets
09:41 – 13:02: The “aha moment”—AI agents closing real deals, efficiency parity with humans
17:51 – 23:51: Will AI replace sales? Which roles disappear, and when?
23:51 – 26:02: Concrete advice for salespeople to future-proof their career
28:41 – 39:35: Deep dive: which agents are deployed, which vendors, how agents are trained
42:25 – 47:32: How to make AI outbound “not terrible”; why most emails are bad
54:02 – 57:17: The orchestrator role: Why you need someone technical & internal
68:23 – 73:30: What’s changing and what’s not: sales, support, phone calls, and more
87:32 – 90:17: How to talk to your team about AI change; realistic outlook on job impact

Structured Breakdown of Main AI Sales Agents and Stack

| Agent Name | Function | Tool/Stack | Notes | |-------------|---------------------------------------------|--------------------|---------------------------------------------| | Delphi | Digital clone/Jason “bot” | Delphi | Closed sponsorship on its own; support, event Q&A | | Artisan | Outbound SDR (prospecting, email) | Artisan | High volume; startup with hands-on support | | Qualified | Inbound qualification (chat, site bubble) | Qualified | Live 24/7; sets meetings, filters non-fits | | AgentForce | Reactivation of “unqualified”/lapsed leads | Salesforce (AgentForce) | 70% response on “discarded” leads |

Quick-Access Resources

SaaStr AI Tools & Agents List: saster.ai/agents
Try SaaStr Tools: saster.ai
LennyBot AI Example: lennybot.com

Final Takeaways for Listeners

Embrace AI: Don’t fight the future—learn how to train and operate AI agents, as this is where career opportunity lies.
Best Practice: Start with support/chat bots if you’re new, then expand to outbound/inbound.
Invest in Orchestration: The technical “shepherd” is your force multiplier—grow or promote this role internally.
Get Hands-On: Founders and GTM leaders: do the work yourself before delegating or hiring agencies/consultants.
Stay Honest & Positive: Be transparent with your team; AI won’t lead to mass layoffs, but it will change who gets hired and promoted.
Stay Excited: AI is creating transformative opportunities for those who seize them.

Memorable Closing Advice

“If you’re not excited [about AI] … over the holidays, fire up your browser in incognito, try your product as a new user, see where it’s broken … then go buy that agent and fix it. And then you will have the passion that we have.”
— Jason Lemkin (85:30)

Episode offers a must-listen, firsthand look into the future of sales and go-to-market enabled by AI—with tactical advice for thriving amid the disruption.

Podcast Summary

Lenny’s Podcast: Product | Career | Growth

Episode Overview

Key Discussion Points & Insights

1. The Shift from Human to AI Sales Teams

SaaStr moved from around 10 full-time salespeople to 1.2 humans (one full-time AE, part-time Chief of AI) and 20 AI agents.
Each former human’s desk is now labeled with the agent’s name (e.g., Reply, Quality, Arty).
Agents work 24/7—including nights, weekends, and holidays.

“We have 10 desks that used to be go to market people. They're all just labeled with our agents... Agents work all night and they work weekends and they work on Christmas.”
— Jason Lemkin (00:04)

SaaStr's business performance is roughly the same with AI agents as it was with its fully-human team, but operations are more efficient and scalable.
The biggest AI impact: replacing the “mid-pack” and mediocre roles that are transactional or repetitive.

“AI is replacing the jobs people don't want to do today and it is displacing the mid pack and the mediocre.”
— Jason Lemkin (00:22, 13:02)

2. How AI Agents Work at SaaStr

AI agents handle:
- Outbound prospecting (sending emails, cold outreach)
- Inbound qualification and lead handling
- Re-engaging lapsed customers
- Customer support (answering event questions, handling refunds, etc.)
AI agents must be trained using the best scripts, best people, and high-quality data; they do NOT work “out of the box.”
- Training involves ingesting data, iterating, and human oversight.

“It takes time to train these agents. They don't work out of the box, but when you dial them in, when you take your best person or your best script and you train an agent with your best person and best script, that agent can start to become a version of your best salesperson.”
— Jason Lemkin (09:41)

Vendors matter: Choose those that will “do the work with you”, not just sell you software.

3. The Future of Sales & Go-to-Market Roles

SDRs/BDRs (Sales/Business Development Reps):
- Entry-level, email-based, and qualifying SDR roles will be “90% displaced by AI next year.”
- In-person, higher-touch sales may remain, but classic inbound/outbound email roles will shrink dramatically.

“The classic SDR junior kid that is hired out of college to send emails … we don't need them… They should be extinct next year.”
— Jason Lemkin (19:27)

Account Executives (AEs):
- The best will gain “superpowers from AI” and become more productive.
- A growing role for “agent orchestrators” who manage multiple AI agents.
Orchestration/Oversight:
- A new, critical role has emerged: someone must oversee and “QA” agents, manage data segmentations, and ensure agents don’t generate conflicts or errors.
- Typically, this is a technical, nerdy marketer, product manager, or ops person (not a classical salesperson).

“It is so much time now to manage these 20. This is interesting. We can't, I don't know when we're going to do the 21st. We may be full.... the agents never sleep, right? So it is so much time now to manage these 20.“
— Jason Lemkin (39:35)

4. Advice for Salespeople & Leaders (Career Tactics)

For Sales Leaders:
Learn to deploy, train, and iterate with AI agents yourself. Don’t delegate; become hands-on. This makes you “hyper employable.”
For Junior Salespeople:
Embrace the tools your company adopts. Become the best at working with agents and accept the new level of productivity and transparency.
For Founders/Startups:
Don’t build GTM AI tools yourself unless you have world-class technical resources. Instead, pick vendors who will act as “forward deployed engineers” and guide you through successful implementation.

“If you can go do this and get it live into production, you're hyper employable.”
— Jason Lemkin (26:02)

5. Best Practices—Making AI Sales Actually Work

Successful AI-driven playbooks:
- Use your BEST reps’ emails as templates for AI; don’t let mediocre or lazy humans define your AI training.
- Constantly QA and iterate. AI will go off-track if not closely managed.
- Segment your CRM/leads so agents don’t overlap or create chaos.
- Choose software partners based on their willingness to roll up their sleeves and help you train and launch—not just features.

“Take your best person on your sales team, your best marketer you have ... use that as the template for your AI.”
— Jason Lemkin (42:33)

Quality Management:
Many bad AI outbound emails are the result of poor training or lazy implementation. A well-trained agent, using your best human’s approach, is “pretty good—and for many teams, better than their average rep.”

6. What Stays the Same vs. What Changes

What’s Changed:

24/7 productivity; instant and scalable outbound/inbound sales.
Entry-level sales paths are vanishing—no more “college grad SDR” pipelines.
Expectations for customer response times and qualification have risen dramatically.

What’s the Same:

The core sales “plays” (events, webinars, outbound, relationships) all still work.
High-touch, high-value, highly personalized sales (e.g., large enterprise deals) are still human-driven.

“All the plays work. It's the playbooks that are kind of broken in the age of AI, all the plays work.”
— Jason Lemkin (14:30)

7. The “Agent Orchestrator” Role

This is the new secret weapon—a highly technical, data-driven operator who manages, segments, and improves the fleet of AI sales agents.
Usually comes from a product, marketing, or ops background (rarely sales).

“This is critical. And ... the chief orchestrator officer ... is a new skill set... you have to grow this resource at home today.”
— Jason Lemkin (54:02)

8. What to Watch Out For / Future Predictions

Organizations will still hire more salespeople net-net, but only the best/hyper-productive; AI “raises the bar.”
Agents are exhausting to manage—don’t underestimate the QA and oversight need.
The next few years may see agent and orchestration “max out”—organizations will hit the limit of how many agents they can handle operationally.

Notable Quotes & Memorable Moments

On Replacing People with AI:
- “We are going to push the limits with agents. We're going to put—even if it doesn't quite work.”
  — Jason Lemkin (08:19)
On The Risks for Sales Professionals:
- “If you can go do this, you're hyper employable.”
  — Jason Lemkin (26:02)
- “AI can be people people, too.”
  — Jason Lemkin (74:12)
On Quality & Training:
- “Agents are really good at AB testing. They're really good at creating variants ... But you just haven't seen a well trained agent.”
  — Jason Lemkin (43:33)
On The Opportunity:
- “If you have those skills. Even though we're not going to need these SDRs ... there is so the amount of revenue and growth in AI leaders is so phenomenal ... you may become more valuable, have a better experience in DTM and ... be better paid.”
  — Jason Lemkin (77:21)
On Staying Honest With Teams About Change:
- “Be honest about it. Be honest that for the best people, it will make them more productive. For the best people ... they will be better at their job. And if it is a threat to some of the folks on the team, the future is coming anyway. We might as well embrace it.”
  — Jason Lemkin (87:32)

Key Timestamps

00:00 – 03:00: SaaStr’s transition to 20 AI agents, what that looks like day-to-day
05:45 – 09:00: How SaaStr became a community, monetized with sponsorships/tickets
09:41 – 13:02: The “aha moment”—AI agents closing real deals, efficiency parity with humans
17:51 – 23:51: Will AI replace sales? Which roles disappear, and when?
23:51 – 26:02: Concrete advice for salespeople to future-proof their career
28:41 – 39:35: Deep dive: which agents are deployed, which vendors, how agents are trained
42:25 – 47:32: How to make AI outbound “not terrible”; why most emails are bad
54:02 – 57:17: The orchestrator role: Why you need someone technical & internal
68:23 – 73:30: What’s changing and what’s not: sales, support, phone calls, and more
87:32 – 90:17: How to talk to your team about AI change; realistic outlook on job impact

Structured Breakdown of Main AI Sales Agents and Stack

Quick-Access Resources

SaaStr AI Tools & Agents List: saster.ai/agents
Try SaaStr Tools: saster.ai
LennyBot AI Example: lennybot.com

Final Takeaways for Listeners

Embrace AI: Don’t fight the future—learn how to train and operate AI agents, as this is where career opportunity lies.
Best Practice: Start with support/chat bots if you’re new, then expand to outbound/inbound.
Invest in Orchestration: The technical “shepherd” is your force multiplier—grow or promote this role internally.
Get Hands-On: Founders and GTM leaders: do the work yourself before delegating or hiring agencies/consultants.
Stay Honest & Positive: Be transparent with your team; AI won’t lead to mass layoffs, but it will change who gets hired and promoted.
Stay Excited: AI is creating transformative opportunities for those who seize them.

Memorable Closing Advice

“If you’re not excited [about AI] … over the holidays, fire up your browser in incognito, try your product as a new user, see where it’s broken … then go buy that agent and fix it. And then you will have the passion that we have.”
— Jason Lemkin (85:30)

Episode offers a must-listen, firsthand look into the future of sales and go-to-market enabled by AI—with tactical advice for thriving amid the disruption.

We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr)

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Summary

Podcast Summary

Lenny’s Podcast: Product | Career | Growth

Episode Overview

Key Discussion Points & Insights

1. The Shift from Human to AI Sales Teams

2. How AI Agents Work at SaaStr

3. The Future of Sales & Go-to-Market Roles

4. Advice for Salespeople & Leaders (Career Tactics)

5. Best Practices—Making AI Sales Actually Work

6. What Stays the Same vs. What Changes

7. The “Agent Orchestrator” Role

8. What to Watch Out For / Future Predictions

Notable Quotes & Memorable Moments

Key Timestamps

Structured Breakdown of Main AI Sales Agents and Stack

Quick-Access Resources

Final Takeaways for Listeners

Memorable Closing Advice

Summary

Podcast Summary

Lenny’s Podcast: Product | Career | Growth

Episode Overview

Key Discussion Points & Insights

1. The Shift from Human to AI Sales Teams

2. How AI Agents Work at SaaStr

3. The Future of Sales & Go-to-Market Roles

4. Advice for Salespeople & Leaders (Career Tactics)

5. Best Practices—Making AI Sales Actually Work

6. What Stays the Same vs. What Changes

7. The “Agent Orchestrator” Role

8. What to Watch Out For / Future Predictions

Notable Quotes & Memorable Moments

Key Timestamps

Structured Breakdown of Main AI Sales Agents and Stack

Quick-Access Resources

Final Takeaways for Listeners

Memorable Closing Advice