This Week in B2B + AI: Lenny + Jason, Backfilling with AI, Navan Crushes But Crashes, A Big Turnaround For SaaStr
"A mid-level sales leader who's built their career managing a team of 8-10 SDRs is looking at a future where that team doesn't exist—which means their job doesn't exist either."
Jason Lemkin on B2B + AI | Week 1
New year, new format. I’ve been writing at SaaStr for 13 years and 4,621 posts, but this is something different—a weekly personal take on what I’m actually seeing in B2B and AI. Less polished, more honest. Let’s see if it works.
1. The Lenny Episode Is Taking Off
Back on Lenny’s Podcast for the second time—this one about replacing our sales team with 20 AI agents. Same revenue, 1.2 humans instead of 10.
It hit #1 on his channel within hours. 15K views in 24 hours, now on pace to break 100K, which would put it ahead of Tobi Lütke (Shopify CEO), Bret Taylor, Elena Verna, and most of his other guests. On X, Lenny’s post about the episode hit 76K views with 400 likes and 900 bookmarks. The topic clearly has heat.
The comments are the interesting part. The mid-level sales execs are the most skeptical—poking holes, saying it only works because we’re selling event tickets to an established audience, saying it’s disingenuous to position this as relevant to “real” SaaS sales orgs.
The people most threatened by a technology are usually the last to see it clearly. They have the most incentive not to. A mid-level sales leader who’s built their career managing a team of 8-10 SDRs is looking at a future where that team doesn’t exist—which means their job doesn’t exist either. Of course they’re going to poke holes.
The smart play isn’t to argue about whether AI will replace sales roles. It’s to ask: how do I become the person who manages 20 AI agents instead of 10 humans? That’s the new job. And it’s more valuable, not less.
Jan 1 was intentional timing, by the way. I launched EchoSign on Jan 1, 2006. SaaStr University on Dec 31—it hit #1 on ProductHunt. Conventional wisdom says don’t publish on holidays. Everyone’s off, no one’s paying attention. The reality is the opposite: supply of content craters while demand stays steady. People are on their phones, bored at family gatherings, looking for something to read. And there’s almost no competition in the feed.
2. We’re Backfilling Our Next Departure with an AI Agent
Someone on our team—4+ good years with us—decided to change industries. Great person. We’ll miss them.
We’re replacing them with an AI agent.
Not because we wanted to. Because it’s what makes sense now. We’ve been quietly testing this across the org: AI SDRs sending 3,000+ emails/month vs. 75-285 from humans. Better response rates. Never takes a sick day.
Should we be worried about jobs? Yes. Shopify’s Tobi said teams must prove AI can’t do the work before asking for headcount. Salesforce is hiring no new salespeople in 2026. IBM says AI will displace 10% of jobs.
This isn’t coming. It’s here.
3. SaaStr AI Annual 2026 Ticket Sales: Up 156%
December ticket sales for SaaStr 2026 (May 12-14 in SF Bay) were 181% of 2024. Overall we’re running at 156%.
The old SaaS is dead but B2B is stronger than ever. It’s a different use case—AI-fueled, more efficient, fewer humans—but it’s back.
Many of us never saw the downturn. But those selling to tech companies felt it. Now even they’re seeing budgets open up.
May 12-14 2026, SF Bay. 10,000+ of the Best of the Best in AI + B2B.
4. 4,877 Days, 4,621 Posts
August 22, 2012 to today. I’ve written a SaaStr post every single day.
That’s ~3.5 million words—more than 2x the Harry Potter series. 30+ full books. Posts used to take 2-3 hours. Now 30-45 minutes.
What’s changed: people skim more. Time on page under 60 seconds. Social trained everyone to consume in fragments.
What hasn’t changed: the founders reading at 2am, desperately googling “when should I fire my VP Sales.” Still worth it.
More here.
5. The Navan IPO Tells You Everything About B2B Right Now
Navan finally went public. After years of confidential filings, pushed timelines, and a rebrand from TripActions, they rang the bell on October 30th, 2025.
Then the stock dropped 20% on Day One. Today it’s trading around $17—that’s 32% below the $25 IPO price. The company that was once valued at $9.2 billion in the private markets now sits at roughly a $4 billion market cap.
Here’s the thing: Navan is a great company. ~$800M ARR. Growing almost 30%+. 71% gross margins. 10,000+ customers including Unilever, Adobe, and OpenAI. They have an AI assistant (Ava) handling 50% of customer interactions. This isn’t a broken business—it’s a legitimate SaaS leader.
And it’s trading at 4-5x ARR. Yes, it’s loaded with a ton of debt. But still.
Meanwhile CoreWeave trades at 30x+ revenue with 60% customer concentration and $18B in debt. The difference? Three letters: G-P-U.
Today there are exactly two types of B2B companies. AI infrastructure, where you can lose billions, have massive customer concentration, and still double after IPO. And everything else, where you need to be profitable, diversified, growing 30%+, and you still trade at 4-5x.
Andreessen Horowitz just bought $25M+ of Navan stock on the open market—50%+ off IPO price. When a16z is buying the dip and it barely moves the stock, that tells you everything about where the market’s head is at.
If you’re building B2B software that isn’t pure-play AI infrastructure, brace yourself. 5-6x ARR is the new normal. 4x if the market doesn’t love your story.
More here.
6. From -19% to +47%: What Happened to SaaStr Traffic
At the start of 2025, SaaStr website traffic was declining. Down 19% year-over-year.
By end of year: up 47%. That’s a 66% swing.
What changed? We went all-in on AI content. Not “AI will change everything” hot takes. Actual implementation stories. What tools work. What failed. Real numbers from real deployments.
The audience told us what they wanted. We finally listened.
More here.
7. 37 Pods with Harry and Rory. So Far.
Every single week for the last 9 months, Harry Stebbings, Rory O’Driscoll, and I got together and recorded. Didn’t miss a week. 37 episodes.
We captured the entire AI transformation in real time. From “is this real?” to “we’ve deployed 20 agents and here’s what happened.”
Three investors with $3B+ in combined AUM telling the truth about what’s actually working. No guests to be polite to. Just us arguing about what matters.
My favorite format of the year.
8. Why I’m Trying Substack (Again)
I’ve tried to make cloud.substack.com work for years. 5,000 subscribers.
My theory: the content has been recaps of things that exist elsewhere. SaaStr talks, podcast transcripts. Useful, but not differentiated.
Substack rewards personal, native content. Voices, not brands.
So here’s the experiment. A weekly personal take. Maybe it works, maybe it doesn’t. But the list growth problem is the real problem. YouTube views and X impressions are rented attention. The email list is owned.
We’ll see.
9. From This Week’s Pod with Harry + Rory
Every week, Harry Stebbings, Rory O’Driscoll, and I record together. Three investors, $3B+ in combined AUM, no guests to be polite to. Just us arguing about what matters.
Here are my top takeaways from this week:
I won’t do a T3D2 investment again.
T3D2 was the old math: triple revenue three years in a row, then double twice. Get to $100M ARR in 6-7 years. That was the playbook.
It’s dead. AI + B2B startups are scaling too fast. Cursor went from $1M to $100M ARR in 18 months. Lovable hit $17M ARR in 4 months. If you’re not finding companies doing $100M ARR in 12-18 months, you’re investing in the past.
It only counts as “AI” if it delivers insane value.
Co-pilots mostly failed. Adding a chatbot to your SaaS product isn’t a strategy. But companies delivering 10x+ ROI—Gamma, ElevenLabs, Cursor, Replit—are seeing budgets appear out of nowhere. The bar for what counts as “AI” has gone way up. If it’s not dramatically better, it’s just a feature.
Founders should stay.
2,221 CEOs quit or got pushed out this year—up 24% from last year. But AI is moving too fast for professional CEOs who need 6 months to “assess the landscape.” The founders who stayed and went all-in on AI are the ones winning. This isn’t the time to hand off the keys.
More here.
10. This Week on SaaStr AI
A few posts worth your time:
The 10 New Rules for Hiring a VP of Sales in 2025 — The old playbook is dead. 70% of VP Sales hires still fail, but now you need someone who’s built AI-augmented teams, not just traditional sales orgs. Read it here.
OpenAI’s GTM Leader: No Commission, 100% Pilot Win Rates — Maggie Hott on how OpenAI builds sales differently. No commission. Pilots that close 100% of the time. The race against incumbents. Read it here.
Should We Be Worried About Jobs in the Age of AI? Yes. — We’re backfilling a departing employee with an AI agent. Shopify, Salesforce, IBM are all freezing headcount. This isn’t theoretical anymore.
—Jason