Jason Lemkin led the seed round via SaaStr Fund in unicorn Owner.com, an AI solution revolutionizing how small restaurants manage their business. Kyle Norton joined shortly thereafter, and after a slow few months, Kyle rocketed the org to almost $100m ARR in just a few years — with growth accelerating at scale. Both Kyle and Jason have shared AI agents, learnings, and more on their AI agent journey and Kyle say down with Jason on the very latest in AI for GTM.
Kyle now manages a 100+ human AI-infused sales team and Jason and Amelia at SaaStr have deployed 20+ AI Agents.
Top 10 Takeaways:
- AI agents are now better than mid-pack AEs and SDRs. Not better than the best. But better than average. And that’s enough to fundamentally change how you build a GTM team.
- The first agent is YOUR job. If you’re a CRO or CMO and you haven’t personally trained and deployed at least one AI agent, you will become obsolete. No agencies, no consultants. You. 30 days of work.
- Pick one tool, not ten. The biggest mistake executives make is running 8-10 vendor bakeoffs. You can’t train 10 agents. Pick two—one incumbent, one startup—and go deep.
- Salesforce is back—but not because of Agent Force. It’s because when you have 20 agents running autonomously, they need a hub. And Salesforce is that hub.
- The middle is gone. You either work harder than ever to hit 10x5x5x5x growth rates, or you join a slow-growth company at 15-20%. The magical 2021 middle where you could have lifestyle AND exceed quota? That’s over.
- Forward Deployed Engineers > Features. Don’t sign a contract until you’ve talked to the person who will actually deploy your agent. The best vendor isn’t the one with the best demo—it’s the one that will help you get into production.
- Every agent takes 30 days to train. No shortcuts. You upload data, review outputs daily, correct mistakes, iterate. The agents that “don’t work” are the ones nobody trained.
- Fix what breaks your heart first. Go to your website in incognito mode. Try to buy something. Try to get a question answered. Whatever breaks your heart—fix that with AI first.
- AI-infused teams are 3x more productive. Kyle’s team at Owner is booking 3x revenue per AE compared to any team he’s ever managed. But that doesn’t mean fewer reps—it means higher quotas and more hiring.
- The $250K SDR is coming. The elite folks—not the ones who think they’re elite on LinkedIn, but the ones who are genuinely 5-10x more productive—will earn 2-3x what they used to. But they’ll be expected to deliver 10x the output.
The Backstory: Why SaaStr Went All-In on Agents
It started with frustration.
We had two salespeople making high market, six-figure salaries. They just quit going into our biggest event. No notice. No reasons. Just ghosted.
I turned to Amelia, our Chief AI Officer, and said: “We’re done with this. I am done paying an SDR $150,000 a year or an AE $300,000 a year for basically inbound, spoonfed leads and renewals—and then having them quit on me.”
Maybe you can be critical of me as a boss. Fair enough. But I’m pretty loyal. I pay people well. Do your job with me, and I’ll stick with you for 20 years. I just couldn’t do it one more time in my career.
So we went all-in. Started in May with 1 AI Agent. Today we have 20+ agents running in production. They’re generating over $1 million in revenue. And here’s the scary part:
Our AI agents are better than a mid-pack AE or SDR.
Not better than the best. But better than the 50th percentile person I’ve worked with over my career. And that changes everything.
The New Reality: Mid-Pack Sales Execs Are in Terminal Decline
Let me be blunt: if you’re a mid-pack GTM professional who doesn’t want to work harder and smarter than a year ago, these jobs are in terminal decline.
We sent 70,000 hyper-personalized emails for SaaStr London using AI agents. They were better than the 7,000 emails humans sent before that. 10x the volume. Slightly better quality.
And here’s what happened when we asked our highly-paid SDR to follow up on a lead I spotted on LinkedIn:
“I’ll add it to my list and get to it when I can.”
Half the time, they didn’t even follow up.
The agent? The agent doesn’t argue. The agent just follows up.
But We’re Still in Inning One
Here’s what most people don’t understand: what we’re doing today with AI GTM is just step one.
Right now, “hyper-personalization” means maybe three dynamic fields in an email. One, really. Maybe we know your company name and your title.
But imagine when AI really pulls in:
- Every competitor you’ve ever used
- Every page you’ve visited on our website for 10 years
- Every interaction you’ve had with our brand
- Every adjacent tool in your stack
Imagine when AI can send an email as good as the one that got me to invest in Owner—an email the founder probably spent several hours crafting with a top 0.1% IQ.
AI should be able to do that. It’s just not there yet in GTM.
When it is? Buy that product immediately.
The Real Reason Agent Deployments Fail
The failures of AI SDRs in 2024 were all LLM-based. The products literally didn’t work before Claude 4. It was slop.
Now? They’re all above the line.
So why do agents still fail today?
Because people don’t roll up their sleeves and train them.
We bought a RevOps tool. Didn’t train it. Didn’t pay attention. Thought it didn’t work. Then we got on a Zoom and I asked our highly-paid AE why we weren’t seeing any data.
He said: “The app doesn’t work.”
I said: “Do you see that Google link in the bottom left? You have to link up your account.”
He linked it up. It showed he’d done nothing for 30 days. He quit that day.
The tool worked fine. We just never put in the 30 days to train it.
The 30-Day Rule
Every agent requires weeks of training before you can go live. Here’s what that actually looks like:
Day 1-7: Ingestion
- Upload your prospectus
- Upload documentation
- Connect to your database (or just your website as a base case)
- The agent creates a list of questions—10, 20, 30 sample outputs
Day 8-21: Iteration
- Read every output. Every single one.
- Correct what’s wrong
- “Owner is great for 100-chain high-end restaurants” → Wrong. Fix it.
- “Owner scales much more now, but our core audience is single-location restaurants with significant to-go business” → Correct.
- The agent remembers. Every day it gets better.
Day 22-30: Production
- Hallucinations become a minor issue
- You’re ready to scale
If you don’t do this? You’ll say the agent doesn’t work. But the agent was never the problem.
Do It Yourself, Dude
Here’s my strongest advice for CROs and CMOs:
If you don’t roll up your sleeves in the age of AI and AI GTM, you will become obsolete.
This is not an agency game. Not today. Maybe in 24 months.
I’m watching executives bring in their 11 agencies from their last job—their Salesforce agency, their outbound agency, their leftbound and rightbound agency from 2015—and they’re all failing.
You are the agency. For now. At least for the first one.
Here’s the brutal truth: if you haven’t trained an agent yourself, you have no idea what you’re talking about. Literally. You will be utterly ignorant in the age of AI.
I did it. Even at this point in my career. I trained the first agent myself—every single day for a month. First thing in the morning. See what the agent said, see what’s wrong, start editing and changing.
Then I proved it to Amelia. Then she did all the rest. She’s better and smarter than me. But I had to do the first one to even know what I was telling her to do.
How to Pick Your First AI Agent
Step 1: Pick one tool that solves a medium or higher-ranking problem.
For many folks, it’s AI SDR. But it doesn’t have to be. Could be RevOps. Could be support. Pick something you’re passionate about—or pick whatever breaks your heart when you go through your own customer journey.
Step 2: Find the right vendor partner.
Don’t sign the contract until you talk to your Forward Deployed Engineer. I literally did this the other day: “I want to talk to my FDE. I don’t even need a demo. Who’s going to help me deploy this agent?”
Still waiting to hear back. So that tool won’t be our first agent.
If the vendor won’t connect you with your deployment team, find another vendor. I would rather have a worse vendor and know who’s deploying my agent than the world’s fanciest brand where I don’t know who’s going to do it.
Step 3: Budget for $50-100K, not headcount.
The first one is not about headcount. It’s about budget for one tool. You need 50K, 60K, or 100K—which is not nothing, but find the budget.
Then you deploy it yourself, prove the ROI, and walk back to your CFO with data:
“We just sent 70,000 automated emails. They’re better than humans. It generated 15% of the revenue for SaaStr London. Can I have some more budget?”
Sure.
The Two-Vendor Bakeoff
We talk to so many folks doing bakeoffs of 8-10 vendors.
In the old days, pre-AI, you could kind of do this. Buy SalesLoft, let the reps figure it out.
Now? Each agent takes 30 days to train. You literally cannot do 10. It’s impossible.
Do two.
Pick one you already use (Intercom’s Finn, Zendesk’s AI, Salesforce’s Agent Force) and one hot startup that someone like you is using successfully.
Ask for references. Send an email. Kyle from Owner will respond. Marshall from Manglement will respond. They’re all getting 50 reference requests a month. Just don’t ask for a call—send an email and they’ll give you a one-word honest answer.
That’s enough.
Because here’s the honest truth: all the leading agents are good. They’re all so much better than pre-AI that what matters is can you get it into production?
These tools are evolving so quickly that during 2026 they’re going to converge. Feature parity used to take years. Now it takes weeks.
So just pick the one that’s the right match for you. The one with the best deployment support. And go.
The Lowest Hanging Fruit: Fix Your Inbound
If you want the single easiest win, it’s adding AI to inbound.
There is no excuse today for prospects not getting instant answers to their questions.
There is no need for some 21-year-old SDR to qualify whether I’m worth their time to talk to an AE.
Go to saastrannual.com. Talk to the digital Amelia—video, text, audio, however you want. She’ll answer your questions. If you want to sponsor, she’ll qualify you instantly. If you’re not a fit, she’ll tell you.
No waiting. No scheduling calls. No hoops.
I tried to buy a 10K product recently. Emailed the rep. They passed me to someone else. That person wouldn’t answer a single question until I got on a call.
If they’d had an AI bot, I would have bought it in real time.
That process is just not OK anymore. It’s no longer necessary. There’s no need to have high-friction sales that benefits some team’s funnel in theory.
AI can score a lead better than a human. Today.
Why Salesforce is Back
Kyle and I are both leaning into Salesforce more than ever. Here’s why: when you have 20 agents working autonomously, they need a hub. Somewhere for their data to meet. Somewhere to resolve conflicts.
Salesforce is that hub.
We use three different AI SDRs working with three different segments of our base. They all push their learnings back into Salesforce. They all share data. It’s a virtuous circle.
The potential conflict? We pay more for those agents than we pay for Salesforce. Which is an existential question for Marc and his team. The agents are extracting the majority of the value.
That’s why AgentForce has to win. That’s why they have 2,000 people working on it.
But here’s my take after being one of the few in production with both Agent Force and competitors:
- Agent Force is more work to set up
- But it’s as good or better in production
- The native integration with Salesforce data actually makes a difference
- The emails are pretty similar across all the leading tools
If Salesforce can make Agent Force more turnkey, it’s really going to win.
The 3x Productivity Question
Kyle’s AI-infused team at Owner is 3x more productive on a per-AE basis than any team he’s ever managed.
So does that mean hire fewer reps? Not exactly.
If it were truly 3x, you could probably get away with a 30-40% smaller team and still hit your growth numbers. Not a third—but 30-40%. But the hottest AI companies can’t find enough people to hire. The quotas at OpenAI for the enterprise team are really high. And they still don’t have enough people.
What’s changing is leverage.
Traditionally in sales, there’s been no leverage. Every year you need to add more reps. In fact, there’s anti-leverage—it gets harder to get that incremental dollar. For folks that crack the code with AI, there may be leverage for the first time. And that means the elite folks—the genuinely 5-10x more productive ones—should be paid 2-3x more than before. No problem paying someone who manages 20 agents two or three times more than a traditional outbound director.
But we’re expecting 10x the productivity. It’s not charity.
Triple Triple Double Double Isn’t Enough Anymore. At Least Not for VCs.
Let me be clear: triple triple double double is plenty good to build a multi-billion dollar company. Put it in a spreadsheet. 2→6→18→36→72. You’ll build something real.
Three or four years ago, 50% of VCs would fund you at that growth rate.
Today? Maybe 10%.
It’s not 0%. But you have to find someone who really believes.
The same amount of money is going into venture as the peak of 2021, but to less than half the companies. For startups, this means:
- Whatever capital you have needs to last
- Recruiting is harder because the best people want to work at the fastest-growing companies
- You need to be ruthlessly honest about your fundability
Go to saastr.ai/aivc. Upload your investor deck. It will tell you your exact percentage odds of getting funded based on all the benchmarks. A founder just below triple triple double double was confident they could raise. The AI said 38%. It changed their perspective.
Pick Your Path
Here’s the bifurcation that’s happening:
Path 1: Work harder than you ever have.
If you want venture-scale outcomes—10x 5x 5x 5x growth rates—be ready to work harder than ever. Kyle is working the hardest he ever has. I’m working the hardest I ever have. At Owner, even with all the tailwinds, even with an awesome team, Kyle’s still grinding.
This is what it takes now.
Path 2: Join something slow-growth.
The folks growing 10-15-20% a year need people too. Good cash comp. The right amount of pressure. Taking a company from 20% to 25% growth is a big win for the year.
If you don’t want to be thinking about work constantly, if you want to log off at 4 or 5pm—I’m not mocking that. We’re human beings. But pick your path.
The middle is mostly gone.
In 2020-2023, you could have it all. Lifestyle, work from home, 20-30 hours a week, exceed quota because of structural tailwinds. That doesn’t exist anymore.
Even the fastest-growing startups are either lean, back in office, or high intensity. There is no magical middle.
Be honest about what you want. Then pick.
Top 5 Mistakes Execs Make with AI GTM Agents
1. Running 8-10 vendor bakeoffs instead of picking two and going deep.
You can’t train 10 agents. You don’t have 300 days. Pick your incumbent option and one hot startup, do real deployments of both, and decide.
2. Outsourcing deployment to agencies or consultants.
There are no AI GTM agencies that understand your business well enough to train your agents. Not yet. Maybe in 24 months. Today, you are the agency.
3. Buying a tool and putting it on the shelf without 30 days of training.
Every agent that “doesn’t work” is an agent nobody trained. You have to upload data, review outputs daily, correct mistakes, and iterate. Every single day until it works reliably.
4. Not talking to the Forward Deployed Engineer before signing.
The best vendor isn’t the one with the best features. It’s the one that will help you get into production. Don’t sign until you’ve talked to the person who will actually deploy your agent.
5. Giving AI tools to individual reps to “figure out on their own.”
A CMO at a $10B company told Amelia they were going to buy an AI SDR tool and just hand it to each SDR to figure out—no training, no centralization. That old paradigm of “buy SalesLoft, let reps run their own cadences” doesn’t work with agents. You need a nerdy GTM person at the top of the stack managing the whole thing.
Quotable Moments
From Jason Lemkin
“I am done paying an SDR $150,000 a year for basically reaching out to with mediocre emails to leads that are already high qualify—and then having them quit on me.”
“Our AI agents are better than a mid-pack SDR, and in part, AE. Better than the 50th percentile people I’ve worked with over my career. And so we just don’t need them.”
“If you don’t roll up your sleeves in the age of AI and AI GTM, you will become obsolete.”
From Kyle Norton, CRO Owner
“We’ve got nine high-impact production use cases of AI. Our booked revenue per dollar spent, on a per-AE basis, is 3x any team I’ve ever managed before.”
“We built our cold outbound email program infrastructure in three weeks. Everybody else told us that was a multi-month project.”
“Even at Owner, even with all the tailwinds, even with an awesome team—I’m still working the hardest I’ve ever worked.”
Try our AI tools at saastr.ai — AIVC for fundability analysis, AI agents directory, and more.
