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30Right Now, We Run 4+ AI SDR Agents. Here’s Why.
We’ll take four A+ specialized AI agents over one B+ all-in-one platform every time. At least … for now. The
6/1/2026
Entrata at $575m ARR Growing 23% Is First of the Next Wave of PE-Backed Software IPOs. The Catch: Almost None of Them Are Accelerating.
Entrata filed its S-1 on May 28 to list on the NYSE under the ticker “ENT.” It’s the multifamily prope
6/1/2026
How Papaya Global Built a Production Compliance Agent With Claude, Lovable, and Supabase. And No Engineers
Payroll compliance is a business where one wrong answer can cost $250,000. Papaya Global runs it across 160 countries, a
6/1/2026
The GTM Stack Anthropic Uses From Its Head of Industries: Surprisingly Familiar Names. Used In New Ways.
You’d assume Anthropic, of all companies, would be running on some self-grown, cutting-edge AI-native sales platfo
5/31/2026
A Deep Dive With the Replit Team on Our Agents: 10K, QBee, the AGI-ish Bloomberg Beta Email, and Programming in English (For Real)
The Replit team came out in force to SaaStr AI 2026 (from the CEO to the CRO and the President!). They also in an unguar
5/31/2026
One Unexpected Benefit of Our AI VP Customer Success: Customers Yell a Lot Less. Everything Is Just … More Calm.
Agents Really > Humans in Many Cases. If the AI Agent is Really Well Trained and Designed. There’s a part of runni
5/30/2026
AI App of the Week: Delightloop, the AI Agent That Closes Deals With Physical Gifts
For years, B2B gifting was a manual, expensive afterthought. A field marketer would spend 200 hours a quarter sourcing t
5/30/2026
How One AI Teammate Beat a Stack of 20 AI Sales Agents With Vivun’s CMO
Most go-to-market teams spent the last 18 months buying an agent for every job. Gartner told them to. The advice was to
5/30/2026
The SaaSpocalypse Is Officially Over. Public Software Is Back to Green at the Index Level. But The Gains Aren’t Remotely Even.
The public software basket is back green for 2026. After the roughest start to the year for software stocks… ever.
5/29/2026
How Our AI Agent Booked 614 Meetings from 442K Chats, And Why B Leads Are Pure Gold If You Add AI. The Top Learnings from Agent’s Day of SaaStr AI Annual 2026
The final day at SaaStr AI Annual was our agent stack deep dive day. Amelia and I walked through the 20+ agents we run o
5/29/2026
Salesforce Just Reaccelerated Growth at $45B+ ARR. It Took the Entire Kitchen Sink. 5 Learnings.
Reaccelerating growth at scale is the hardest thing in B2B. Almost no one does it. The law of large numbers is tough to
5/29/2026
20VC x SaaStr This Week: Anthropic Hits 70% Margins, OpenAI Files Its S-1, and Nvidia Yawns at $58B
We did the 20VC x SaaStr episode this week with Harry Stebbings and Rory O’Driscoll, and by the end something funn
5/28/2026
AI PR Is Killing Your Startup’s Chances With the Media
Yeah. I never blocked any domains or people pre-AI … but now … every day The rotation and throway does get around it par
5/28/2026
Gartner: AI Software Spending to Grow 60% to $453B in 2026. And Another 41% to $638B in 2027
Gartner released its updated worldwide AI spending forecast last week . And per their latest data, AI software spend is
5/28/2026
Datadog Stock Is Up +66%. Here Are 5 Reasons Why, And Why It’s the Cleanest AI Beneficiary in B2B
Guess whose stock Is up +66% year-to-date? And trades at 20x ARR? In the midst of the most challenging run for software
5/27/2026
Dropbox Hit $1B Faster Than Any B2B Company Ever. But Now, It’s The End of an Era
An end of an era Of my generation of SaaS CEOs, no star burned brighter than Dropbox It grew to $1B ARR faster than any
5/27/2026
How Owner.com’s CRO Is Closing $2M+ in ARR Per Rep With AI: 5 Things You Can Steal
At SaaStr AI 2026 , Kyle Norton, CRO of vertical AI leader for restaurants Owner.com, walked through how his team is gen
5/26/2026
For Frack’s Sake, It’s Not Too Late to Ship an Epic AI Agent. And Get Back to Real Growth.
So I spent the other day writing a fairly dark post about how most traditional B2B leaders will slowly atrophy to nothin
5/26/2026
Top 10 Learnings From Building Our Own AI VP of Customer Success “Qbee”
We’ve now rolled out 21+ AI agents and 12+ vibe coded apps at SaaStr AI , used 1,100,000+ times. AI SDRs. An AI VP
5/25/2026
Dear SaaStr: How Do The Best Sales Leaders Retain Their High Performers?
Dear SaaStr: How Do The Best Sales Leaders Retain Their High Performers? A few ways I’ve observed that the best sa
5/25/2026
Why 95% of Customer Success Managers Can’t Be Turned into Forward Deployed Engineers. And What That Means.
Every B2B company right now is staring at the same problem: they need more Forward Deployed Engineers, they don’t
5/24/2026
The Agents Episode #005 is Out! Our 2 AI VPs Cost $257/Month, a Website Willed Itself Into Becoming an Agent, and QB Sent 83 Personalized Emails at 12:20am
Amelia and I just recorded Episode 005 of The Agents right before 2026 SaaStr AI Annual. You may have missed it in all t
5/24/2026
Even a Mediocre Prompt Can Build Pretty Good Software Today
Here’s the exact prompt I typed into Replit the other day “ok i have an idea where we built a new speaker ca
5/23/2026
SaaStr AI App of the Week: Helply. The Bootstrapped B2B Support Platform That’s Free Forever, Charges Only When AI Actually Resolves a Ticket, and Showed Up to SaaStr AI 2026 With Giant Pandas
The Bottom Line: Alex Turnbull bootstrapped Groove from $0 to $5M ARR as a solo founder over a decade. Then he bet again
5/23/2026
Forget “Would You Hire Them Again.” The Real Test Now Is Whether You’d Replace Them With an Agent.
For our entire careers in tech, the standard management test has been: “Given what you know now, would you hire th
5/22/2026
20VC x SaaStr: Anthropic at $900B+, Salesforce Spends $300M on Tokens, SpaceX Files for the Biggest IPO in History, and Why the Tech Lash Is Just Beginning
With Harry Stebbings, Jason Lemkin, and Rory O’Driscoll Anthropic is closing $30 billion at a $900 billion valuati
5/22/2026
How Anthropic Rebuilt Its Sales Org From Scratch When Demand Went Vertical: 54% of New Enterprise Logos Now Come Self-Serve
When Claude Opus 4.6 shipped in December 2025, Anthropic’s commercial team came back from winter break to find dem
5/21/2026
The Modern GTM Org in 2026: 20-30% Leaner, 9x Flatter, ~2x More Net New Revenue Per Rep. The Latest from ICONIQ Growth.
ICONIQ just released their latest 2026 GTM benchmark report, surveying 150+ B2B software companies in January . The find
5/21/2026
Why 10K (Our AI VP Marketing) and QBee (Our AI VP Customer Success) Work So Well: The App and the Agent Are One System
Most of the discussion about AI agents in B2B right now treats the agent as a feature you ship: a chat box, a copilot, a
5/20/2026
5 Interesting Learnings from HubSpot at $3.5B in ARR: 23% Reported Growth, $211M in Buybacks, and a 16% Stock Drop
On paper, this was a strong quarter for HubSpot. Maybe not epic, but strong. HubSpot reported Q1 ’26 with revenue
5/20/2026
投資シグナル
20Claude 4.5 and 4.7 models released in late 2025/early 2026 triggered mainstream adoption of agentic engineering, creating an unprecedented competitive gap for early adopters.
Product fluency is becoming the leading sales indicator in fast-evolving SaaS, replacing traditional sales metrics, as reps must understand weekly product changes to answer customer questions effectively.
Replit is demonstrating 10x-100x human productivity amplification through agentic engineering, with internal agents like 10K (an autonomous VP of Marketing built on Replit) delivering output that exceeds traditional software matching systems.
Agentic software development is entering exponential productivity phase with agents becoming commonplace within 18-24 months, fundamentally shifting how software is built from linear story points to compounding velocity metrics.
Sales forecasting is shifting from commit-based projection to consumption-driven inference powered by data warehouse analysis and cohort-based historical patterns.
Customer support tools (Intercom Fin) are being repurposed as enterprise sales automation engines, expanding addressable market beyond support deflection.
Sales support functions are consolidating around AI-powered triage and escalation via chat interfaces, replacing ad-hoc DM coordination and reducing context loss.
AI is collapsing manual sales workflows (proposal drafting, call prep, contract routing) from hours to minutes by pulling context from multiple sources and automating document generation.
Lead qualification and routing is shifting from human-driven enrichment review to AI-powered real-time funnel allocation, enabling self-serve enterprise paths at scale (54% of new enterprise logos).
The future of GTM software is not new category creation but deep platform integration; companies that enable AI-native workflows within existing tools will see significant stock upside.
AI-native sales teams don't require purpose-built AI tools; instead, they rewire existing B2B SaaS platforms (Clay, LeanData, Salesforce, Gong, Ironclad) by injecting Claude at key workflow junctures to automate manual steps.
Papaya Global is building AI-powered compliance agents for payroll operations across 160 countries with multi-agent validation architecture and domain-specific rules to compete against ChatGPT in regulated workflows.
Launching domain-specific agents should prioritize partner-like customers who give honest feedback over broad rollout, with conservative legal framing (guidance vs. advice) to build trust before scaling.
When build costs approach zero via AI coding tools, product defensibility shifts entirely to methodology, domain knowledge, and trust rather than engineering execution.
In regulated B2B workflows, the competitive threat is free general-purpose chatbots already trusted by customers, not other vendors; trustworthiness takes 4x longer to build than the product itself.
Adversarial review architecture (generation, adversarial review, synthesis) with multiple AI agents checking each other is necessary for high-stakes compliance decisions where confident wrongness is the primary risk.
Domain-specific AI agents in regulated verticals require domain expertise moats (rules libraries, compliance methodology) rather than just model capability to be trustworthy and defensible against general-purpose chatbots.
Durable B2B verticals can rapidly improve P&L efficiency once they stop growth-at-any-cost spending; Entrata nearly doubled revenue while flipping from negative margins to $50M+ annual GAAP net income in 3 years.
Market has repriced B2B software multiples significantly down from 2021 levels, with most comparable companies trading 25-40% lower, affecting IPO valuations for profitable SaaS at 20%+ growth rates.
Wave of PE-backed software companies seeking IPO exits faces challenging market dynamics where growth-at-any-cost is no longer valued and acceleration is required; most names lack growth acceleration.