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Feed · Jason Lemkin, GP @ SaaStr

Saastr

SaaStr covers B2B software, AI agents, enterprise infrastructure, and venture outcomes through analysis of market trends, founder experiences, and startup metrics. This page collects 2,493 posts published between April 2013 and October 2026. Recent coverage focuses on Enterprise Software, AI (Horizontal) and Venture Capital & Startups. Saastr publishes roughly 48 posts a month; the best of them appear in the SandHill weekly digest.

2493 posts indexed48 in the last 30 daysEnterprise Software · AI (Horizontal) · Venture Capital & Startups · Marketing & Sales TechVisit site ↗

Saturday, 24 October 2026

1 piece
The Agent-Led Growth Playbook: A 10-Minute Inbound Booking, a 46-of-50 AEO Score, and Why First-Party Data Beats Every Signal Tool | The Agents #017↗
Marketing & Sales Tech · AI (Horizontal)

Friday, 23 October 2026

2 pieces
The New “Ask Your Developer” Is Ask Your Agent. And It’s The Marketing Battle You Have to Win Now↗
AI (Horizontal) · Enterprise Software · Developer Tools
The Double Hockey Stick: Why 1% of Your Users Now Drive 75% of Your AI Costs, and What Figma, Clay, and Higgsfield Are Doing About It↗
AI (Horizontal) · Enterprise Software

Thursday, 22 October 2026

3 pieces
20VC x SaaStr: $20M ARR and Unfundable, Anthropic’s $16.8B Quarter, and Modal at $15.75B↗
AI (Horizontal) · Enterprise Software · Developer Tools
Getty Images Files for Chapter 11 at a ~$910M Run-Rate: 27% EBITDA Margins, 25% Fewer Subscribers, and $0 for Public Shareholders↗
Media & Entertainment
Dear SaaStr: What is the Difference Between a Good Sales Exec and a Great One?↗
Enterprise Software · Marketing & Sales Tech

Wednesday, 21 October 2026

1 piece
Meta’s Muse and Our AI VP of Revenue 10K Built Their Own ‘Secret’ Mailbox to Work Together. Then They Came Up With a Safe Word.↗
AI (Horizontal) · Enterprise Software

Tuesday, 20 October 2026

1 piece
5 Interesting Learnings from Braze at $910 Million in Revenue: A $5.66B Sale to Salesforce, 26% Growth, and Operating Expenses Up Just 6%↗
Enterprise Software · Marketing & Sales Tech

Monday, 19 October 2026

2 pieces
5 Interesting Learnings From Anthropic’s Data on Its Own Workforce: Junior Technical Hiring Down From 27% to 9%, Agents Working 6x the Hours of Humans, and Agents Waiting on a Human 80% of the Time↗
AI (Horizontal) · Venture Capital & Startups
The Top 10 Mistakes I See In The CRO / VP of Sales Hiring Process↗
Venture Capital & Startups · Enterprise Software

Sunday, 18 October 2026

1 piece
Jason’s Takes on This Week’s 20VC x SaaStr: Pro Rata Fights, the First Real AI Price Drop, and Why $500M ARR Isn’t Safe Anymore↗
Venture Capital & Startups · Enterprise Software · AI (Horizontal)

Saturday, 17 October 2026

1 piece
Cloudflare Cut 20%. Atlassian Cut 10%, Mostly Engineers. Bending Spoons Cuts Up to 75%. All Three Are Growing Faster or Earning More. So How Lean Can B2B Teams Really Get?↗
Enterprise Software · AI (Horizontal)

Friday, 16 October 2026

2 pieces
Going Headless: Claudeforce vs. Replit vs. Lovable, Agents Picking Our Vendors, and Two of Our Agents Built Their Own Inbox to Talk Behind Our Back: The Agents #016↗
Enterprise Software · AI (Horizontal) · Marketing & Sales Tech
G2’s 2026 AI Agents Report: Only 9% of Buyers Think Seat Pricing Is Fair, 57% Want Usage-Based, and 74% Will Shop You at Renewal↗
AI (Horizontal) · Enterprise Software

Thursday, 15 October 2026

2 pieces
Meta Ships Muse Wonder, Jev Raises $870M 24 Days After Launch, and Anthropic Cuts Haiku 90%: The Top Takeaways From This Week’s 20VC x SaaStr↗
AI (Horizontal) · Venture Capital & Startups
5 Interesting Learnings from Bending Spoons at $2.8 Billion in Revenue: 126% Growth, 3% Organic Growth, and $1.08 Billion of ARR Bought in 37 Days↗
Enterprise Software · Venture Capital & Startups

Wednesday, 14 October 2026

2 pieces
Want to Steal a Customer From a Competitor? Ask Them What It Would Really Take↗
Enterprise Software · Marketing & Sales Tech
Planning Your 2027 Event Calendar? Our Top 9 Sponsors Averaged 957 Leads at SaaStr AI Annual. And Next Year Will Be Even Bigger↗
Venture Capital & Startups · AI (Horizontal)

Tuesday, 13 October 2026

2 pieces
The #1 Sign Your New CRO, CMO, CCO, CTO Will Fail: They Aren’t Doing It Themselves↗
Venture Capital & Startups · Enterprise Software
Private Equity Fundraising Is Down for the Fourth Year in a Row. Selling Your B2B Company to PE Got Harder Again in 2026↗
Venture Capital & Startups

Monday, 12 October 2026

2 pieces
The Latest SaaStr AI Agent Playbook for GTM Is Out: Everything We’ve Learned Running SaaStr on 3 Humans and 21+ AI Agents, In One Handy Guide↗
AI (Horizontal) · Enterprise Software · Marketing & Sales Tech
Our AI Agent Picked Render Over Railway and Vercel. I’d Barely Heard of It. That’s How You Get Leads in The Agent Age.↗
AI (Horizontal) · Developer Tools · Marketing & Sales Tech

Sunday, 11 October 2026

1 piece
Jason’s Takes on This Week’s 20VC: Loyalty Changed for Good, Agents Now Pick Your Vendors, and When to Take the $2 Billion↗
Venture Capital & Startups · AI (Horizontal) · Enterprise Software

Saturday, 10 October 2026

2 pieces
Atlassian’s Head of AI: We Bolted AI Onto 20+ Apps, Almost Didn’t Ship Chat, and Flipped Our Hiring Toward Juniors↗
Enterprise Software · AI (Horizontal)
SaaStr AI App of the Week: Remote. The $300M Payroll Platform Your AI Agent Can Run↗
HR & Talent · Enterprise Software

Friday, 9 October 2026

1 piece
It Takes 12 Years to IPO. Then Another 2-3 for Your VCs to Get Liquid. And Founders Can Generally Only Sell About ~4% a Year.↗
Venture Capital & Startups

Thursday, 8 October 2026

2 pieces
20VC x SaaStr with MongoDB’s Dev Ittycheria: OpenAI Reaccelerates to a $70B Run Rate, a CRO Jumps to a Direct Competitor, and Agents Start Picking Your Vendors↗
AI (Horizontal) · Enterprise Software · Venture Capital & Startups
5 Interesting Learnings from Cloudflare at $2.8 Billion in Revenue: 36% Growth, a 20% Layoff, and a Stock at 50x Revenue↗
Enterprise Software · Developer Tools · AI Infrastructure

Wednesday, 7 October 2026

1 piece
We Run Monaco, Agentforce and Artisan for Outbound. Why We Still Also Built Our Own “AI ABM” Tool for Our Top Accounts↗
Marketing & Sales Tech · AI (Horizontal)

Tuesday, 6 October 2026

1 piece
How Much of Your Customer Support Can AI Really Resolve? The Best Get About 70%. The Median Is 48%. Here’s the Real Data From 13 Vendors↗
Enterprise Software · AI (Horizontal)

Monday, 5 October 2026

1 piece
You’ll Probably End Up With 40% Of Your Revenue from “International.” Invest Earlier There.↗
Enterprise Software · Venture Capital & Startups

Sunday, 4 October 2026

1 piece
Astra 6 Replaced a Core Engine of SaaStr Connect With Two Words, “DO IT,” Twice in Under an Hour. Then It Said “I Did Not Make That Edit.”↗
AI (Horizontal) · Enterprise Software · Developer Tools

Saturday, 3 October 2026

4 pieces
We Vibe Coded Our Own Calendly. Our AI Agent Pushed Us To Do It, and It Was Right.↗
AI (Horizontal) · Enterprise Software
Why Okta Tripled on … 11% Growth. 5 Interesting Learnings From One of the Biggest Re-Ratings in B2B This Year: 14% cRPO Growth, 30% of Bookings From New Products, and ~50x Forward Earnings↗
Cybersecurity · Enterprise Software
SaaStr AI App of the Week: Chargebee. The Billing System Behind How Gorgias, CodeRabbit, Lambda and Zapier Price AI↗
Enterprise Software · Fintech
We Got a $240,000 Estimate for Agent API Access. Our Agent Suggested a $5 Postgres Instance.↗
Enterprise Software · AI (Horizontal)

Thursday, 1 October 2026

3 pieces
20VC x SaaStr: Anthropic’s S-1 Leaks, Instinct Hits $10 Billion in 33 Days, AMD Buys World Labs, and Meta Poaches MongoDB’s CEO↗
AI (Horizontal) · Venture Capital & Startups
The 10 Most Important Learnings From a16z’s Latest State of Markets: Horizontal B2B Trades at 2.7x Revenue, New Startups Are Growing 500%+, and 55% of Unicorns Have Under 2 Years of Runway↗
AI (Horizontal) · Enterprise Software · Venture Capital & Startups
You’ll Know if That New VP is Going to Fail at the First Board Meeting. Here Are The Clear Tells.↗
Venture Capital & Startups

Wednesday, 30 September 2026

1 piece
“This Is a Pretty Fancy Dinner. That Probably Means I’m Overpaying.” A Dreamforce Lesson From a Top 5 Customer↗
Enterprise Software · AI (Horizontal)
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