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- SaaStr AI App of the Week: Relevance AI — The Platform Where Ops Teams Build Entire AI Workforces (Without Writing a Line of Code)
- Dear SaaStr: Can A SaaS Startup Really Scale With 2 Co-CEOs?
- 20VC x SaaStr: SpaceX at $1.25 Trillion, SaaS Stocks Down 40%, and the Week We Connected a Million AI Agents … Sort Of
- Why a Lot of SaaS is Still “Terrible”: You Can’t Just Talk to It and Have It Do What You Want. It’s Time in the Age of AI.
- Inference Costs Average 23% of Revenue at AI B2B Companies. How Will You Pay For It?
- Dear SaaStr: What’s The #1 Most Important Step in Closing a Deal?
- Dear SaaStr: What Are Some No-No’s When It Comes to Working with VCs?
- Palantir: The Greatest Enterprise Software Company Of All Time Ever? Could Be.
- SaaStr x TBPN: If Growth Isn’t Accelerating, You’re Not an AI Company. And 9 Other Hard Truths for B2B in 2026
- The #1 Error with AI GTM Agents: Assuming They Can Do What Your Team Hasn’t Already Figured Out
- “The Dumbest Idea I’ve Ever Heard” — How Own Became a $2B Salesforce Acquisition
- Dear SaaStr: Which Tactics Always Work to Drive Down Churn, and Drive Up Retention?
- The 2026 SaaS Crash: It’s Not What You Think
- “Digital Jason” Has Answered 73,915 Questions. And It’s Free. Try It!
- Dear SaaStr: How Many Of Our Prospects and Customers Should I Meet Face-to-Face?
- I Wrote Off $4M to $0. My Co-Investor Marked Up the Same Deal to $30M. Here’s What Founders Need to Know About VC Incentives.
- Dear SaaStr: How Long of a Ramp Period Should I Give a New VP of Sales?
- The #1 Conceit in B2B at Scale: Masking a Slowdown in Net New Customers
- The Trade Desk Was Priced for Perfection. Then Growth Slowed. Now It’s the Worst Performing Stock in the S&P 500.
- Dear SaaStr: What Are Some of the Qualities of a “Bad” Startup CEO?
- The Best AI Startups Do the Training For You. It’s On You to Make the Agent Awesome — Not Your Customers.
- Want Leads? Sponsor the Next SaaStr AI Day. And Then SaaStr AI Annual 2026 in May!
- Dear SaaStr: What Are The Signs We’re Ready to Hire More Sales People to Scale?
- 20VC x SaaStr This Week: The $5 Billion Exit That Felt Weird, Why Inference Costs Are the Final Nail for Mid Growth SaaS, and Andreessen’s 2/3 AI Domination
- ICONIQ’s Latest State of AI Report: PLG vs. SLG in the Age of AI; The Real Data on Inference Spend; and The Spike in FDEs
- Why Most B2B Companies Are Failing at AI (And How to Avoid It) with Intercom’s CPO
- Dear SaaStr: How Do You Change the Price of Your SaaS Product Without Upsetting Existing Customers?
- Your Critical Product Goal for 2026: Your Customers Truly, Honestly See Your AI Agent As Part of the Team. For Real.
- The Latest Carta Data: VC Deals Are Up Only 3%, But $$ Are Up 130%
- Dear SaaStr: What Are Some Best Practices for Selling a New Product Into Existing Customers?
- Please Stop Selling Like It’s 2021
- The Top 5+ Pieces of Advice for a First Time VP of Sales
- The New Rule: $500K ARR Per Employee is the New $200K
- Dear SaaStr: How Much Do Founder-CEOs Own at Time of Exit?
- The CEO of An AI Agents Company We Really Love Asked Why We Didn’t Pick Them. Here’s the Honest Answer.
- Dear SaaStr: My Customer Missed the Deadline for AutoRenewal. How Do I Handle This Situation?
- Brex and The Pros and Cons of Hubristic Fundraising
- AI App of the Week: Vivun — The AI Sales Engineer That Actually Does the Work
- Dear SaaStr: What’s The Typical Enterprise SaaS Cancellation Policy For $100k ACV/Bigger Deals? Should The Contract Have a Fine?
- If AI GTM Tools Were Half as Good As Cursor or Replit, It Would Be a Different World Today. They Will Get There.
- a16z’s State of Markets: $5.5T in Private Unicorns, <5 Public Companies Growing 30%, and 8 Other Data Points You Need to See
- Dear SaaStr: How Do You Sell B2B Products to Bigger Enterprise Customers?
- 20VC x SaaStr Are Back: If Figma Isn’t Good Enough, What Hope Is There? Plus OpenAI Ads, Elon vs. Sam, and the $9B Replit Bet
- We Built Our Own AI VP of Marketing. Here’s What It Actually Does.
- Wing Ventures’ State of the AI in the Enterprise: 50% of Pilots Succeed, 53% See Positive ROI, and 70% See AI Replacing Even More Humans
- Dear SaaStr: Is It Common To Oversell in B2B?
- By Late 2025, Replit Got Really Good. Now Imagine If Your Agents Really Could Run 24×7.
- Should You Pay Reps More For Deals They Hunt Themselves? Sometimes. Here’s When.
- Strange World Indeed, January 2026 Edition: The Massive, Unprecedented Divergence Between Public B2B and Private AI B2B
- Dear SaaStr: How Do I Pay My Sales Reps on Monthly Deals?
- The 6 Threat Vectors Attacking Traditional B2B Software in 2026 (And How to Fight Back)
- Dear SaaStr: How Should I Pay Sales Reps When Our Customers Pay Monthly?
- 5 Key Takeaways from Anthropic’s Latest Economic Index: Prompting Is Still Critical, AI Can Handle Massive Tasks If You Break Them Up, and Deskilling is a Bigger Issue Than Unemployment
- Dear SaaStr: What Do The Top 1% of Sales Reps Do … That The Other 99% Don’t?
- We Had a Bug in One of Our 20+ AI Agents. It Took Forever to Figure Out Which One. This is Going to Be a Real Problem.
- Dear SaaStr: Should We Pay Our Sales Reps on Renewals?
- We’ve Built 12+ Vibe Coded Apps Used 800,000+ Times. I Love It. But I Still Have To Maintain Them Every Single Day.
- Meritech’s Look at 2025 Exits: M&A at $587B Hits a Decade+ High … But IPOs Were a Whimper
- Should You Hire a Sales Rep First, Or a Sales Manager?
- 20VC x SaaStr This Week: Anthropic at $350B, OpenAI’s Existential Risk, and Why a16z’s $15B Fund Actually Makes Mathematical Sense
- The Dark Side of Hot Seed Rounds in the Age of AI: When Founders Just Keep the Money
- How Filevine Went from SaaS to AI-Native at $200M+ ARR — And Now Makes More Revenue from AI Than SaaS (A Roadmap for the Rest of Us)
- Dear SaaStr: Is It Worth Working as a Sales Rep?
- Freemium is Back — The AI Edition! But You’ll Still Probably Need 50 Million Active Users for Freemium to Actually Work as a Business Model.
- ElevenLabs Just Hit $330M ARR in 24 Months. It Took Twilio 8 Years to Get There.
- Dear SaaStr: What’s The Lamest Thing You See Sales Reps Do To Close a Deal?
- What’s “Expensive” in AI? The Answer is Changing Fast.
- Dear SaaStr: How Much Money Does a VC Make If Their Investment Sells for One Billion?
- How to Make Sure Your AI SDR is Actually Any Good? You Have to First Copy Your Best Human
- Dear SaaStr: What Happens if a VC Loses All Their Money on an Investment?
- When the Most Expensive LLM Isn’t Worth It: What We Learned Analyzing 3,000+ VC Pitch Decks and 850,000+ Startup Valuations
- If You’re Going to Stick with a Mediocre VP for Now, You At Least Have to Micromanage Them
- Yes, M&A is Back. But Confirmed 3x+ Returns Have Collapsed to Just 7% of Deals. Here’s What That Means for Your Exit.
- Dear SaaStr: How Do You Deal With an Unreliable Co-Founder?
- How Long It Really Takes to “One-Shot” an App: 47,000 Lines of Code Later
- The Change You Need Is the Change You Make. SaaStr AI Annual 2026 Will Help You Get There.
- The Average SaaStr AI Annaul Sponsor Gets 470+ Qualified Leads. Get Them This Year and GO BIG!
- 20VC x SaaStr Is Back!!: Nvidia’s $20B Groq Grab, Meta’s $2.5B Manus Play, and Why “Invisible Unemployment” Will Define 2026
- OneStream Goes Private, Navan at 4x ARR: Are The IPO Markets Really That Open?
- How Personio’s CRO Built an AI-Powered Go-To-Market in Just 6 Months: 5 Lessons and 5 Mistakes
- Dear SaaStr: How Can a SaaS CEO Tell Which Customers are 10+ Year Customers?
- The Rise of Invisible Unemployment in Tech: 2026 Will Be The Year When Everything Really Changes
- 5 Interesting Learnings From Motive at $500,000,000 ARR. And The Match Up With Samsara.
- Dear SaaStr: Should I Fire a Sales Rep That Lied To Several Customers?
- Your #1 Job For January? Deploy An AI Agent — Yourself. Hands On Keyboard
- Your Job In AI + B2B in 2026: Grab The Tailwinds, For Real. It’s Not Too Late. But It’s Different. (Updated with Video)
- Dear SaaStr: As a Co-Founder, How Do I Tell the Team I’m Leaving?
- Right Now, Managing AI Agents is About as Much Work as Managing Humans. Just Different Work.
- SVB’s State of the Markets Report: AI Isn’t More Efficient, VC Dollars Are Even More Concentrated, and M&A is Picking Up But Fewer Deals Make Money
- What To Do When A Customer Wants to Cancel A Contract
- CROs at Slow-Growth Companies Often Aren’t Really CROs. They’re Chief Price Raising Officers.
- Dear SaaStr: What Were Aspects of Your Startup That Were Easier Than Anticipated?
- Hooray, You Got Profitable. That’s Great, But It’s Not Enough. It’s Time To Reaccelerate Growth.
- Dear SaaStr: What Do You Do With Churned Customers?
- How Much Equity to Give Your First Employees: The Real Data from 50,000 Startups
- Dear SaaStr: Should We Drop Customers That Complain Too Much?
- Jason + Lenny are Back!! “The Real Future of AI in Sales”
- We’re Literally Just Getting Started in AI + B2B. Here’s Why 2026 Is When It Gets Real.
- The Navan IPO Reminds Us: AI is On Fire. Everything Else in B2B? Still Really, Really Hard.
- Dear SaaStr: What’s The Best Way to Get Traction After We Have Our First Few Paying Customers?
- A Big Year for SaaStr AI: What We Got Done in 2025
- The 10 Rules For Hiring a VP of Sales in the Age of AI
- The Quirky Math Behind M&A Pricing in Tech: Why $125M ARR Can Be Worth $2B+… And Then Disappear
- Dear SaaStr: How Does a B2B Startup Break Out in a Crowded Market?
- My Top 10 Learnings from 37 Podcasts with Harry Stebbings and Rory O’Driscoll This Year
- OpenAI’s GTM Lead Maggie Hott: No Commissions, 100% Pilot Win Rates, and the Race Against Incumbents
- Dear SaaStr: We’re Running Out of Money and Can’t Raise. When Do You Call It a Day?
- Can You Really Grow in 2026 if You Aren’t Tapping into AI Budget?
- How We Turned Around SaaStr’s Traffic in 12 Months by Going All-In on AI. From a -19% Decline to a +47% Growth.
- Dear SaaStr: What Was the Moment You Knew You Had to Break Up With Your Co-founder?
- One Reason The Best AI B2B Startups Are Growing So Quickly: Truly Insane Value
- Nvidia Created 27,000 Millionaires Already. What It Teaches Us About Getting Rich. And The Power of Going Long.
- Dear SaaStr: My Co-Founder is Threatening to Quit Unless I Give Him More Equity
- AI And The Death of The 2021 Sales Process
- Dear SaaStr: What Are The Best and Worst Parts of a Startup?
- Did You Gain or Lose Market Share This Year? Be Honest.
- Top 10 SaaStr AI Predictions for 2026
- Dear SaaStr: When Bootstrapping a SaaS Product, What Should You Be Aware Of?
- Beware the “Mediocre Recycled”. The Zombie Executives of B2B.
- Have AI Gross Margins Really Turned the Corner? The Real Math Behind OpenAI’s 70% Compute Margin. And Why B2B Startups Are Still Running on a Treadmill
- Dear SaaStr: Is Launching Your SaaS Product Too Early Really A Big Issue?
- 15 Ways Sales Has Changed This Year in the Age of AI
- MongoDB: The Great(est) AI Turnaround Story of 2025
- Dear SaaStr: How Can I Give Better SaaS Product Demos?
- 20VC x SaaStr: 2025’s Winners, 2026’s IPOs, and Why the Tech Lash Is Coming
- The Go-To-Market Playbook Isn’t Broken. You’re Just Running the 2021 Version. LIVE with Jason Lemkin
- Dear SaaStr: When Should You Sell Your Startup?
- A Great Year With Our 20+ AI Agents — But a Rough Week
- Dear SaaStr: How Do I Compete with a Company that has Unlimited Capital — and I Don’t?
- App of the Week: OpenRouter — The Universal API for All Your LLMs
- My Biggest Fear in Investing Now: The $100,000,000 ARR Slowdown
- Dear SaaStr: We’re At $3m ARR Growing 35%. What Does The Future Look Like?
- The Great B2B Bifurcation of 2025: Why Some SaaS Stocks Are Up 142% While Others Are Down 51%
- Is Zendesk Building a Glean Competitor with Its Unleash Acquisition? Not Exactly, But Here’s What’s Really Happening
- Dear SaaStr: Growth Has Slowed for 2 Years Now. What Can I Do To Reignite The Energy?
- Dear SaaStr: We Are Growing Too Fast to Handle the Workload, but We Can’t Afford to Hire New Employees. Help!
- 20VC x SaaStr is Back! SpaceX’s $1.5 Trillion IPO, Lightspeed’s $9 Billion Mega-Raise, and Why All These Late-Stage Giants Staying Private is “The Greatest Gift to Venture in Our Lifetimes”
- What 2,835 VC Funds and $118 Billion Tells Us About Venture Returns Right Now. The Latest Data.
- Why Salesforce Acquiring Qualified is Maybe the Smartest AI GTM Deal of 2025
- The Present and Future of AI in Sales and GTM A Deep Dive with Jason Lemkin and Kyle Norton, CRO at Owner
- Notion at $11 Billion: The Art of Growing Into Your Valuation — And After 14 Years, Into One Of The Next Great B2B IPOs
- Databricks vs. Snowflake at $5B ARR: Same Revenue, 2x Valuation Gap. Here’s Why.
- Dear SaaStr: What Do You Do When Your Startup is Not Growing Anymore?
- We Deployed 20+ AI Agents and Replaced Our Entire Human SDR Team. Here’s What Actually Works. (Video + Pod)
- The $7,500 Migration Fee That Just Cost a Vendor $80,000 ARR. Really, $240,000.
- Klaviyo Adds Co-CEO To Get Back To Product. The Dream, But Does It Work?
- Dear SaaStr: I’m New to B2B Sales. How Do I Create Urgency?
- OpenAI Has Gone From a 6-Month Cliff to… No Cliff At All. And Will “Spend” $6 Billion This Year On Employee Equity. Even at OpenAI, The War for Talent Never Ends.
- Dear SaaStr: I Sold My Company And Made Real Money, But I Still Feel Like A Loser. What Should I Do?
- Why The Greatest Sales Teams Just Kill It On Dec 31. When Everyone Else Has Gone Home. (Updated)
- Even A Slightly Too High Burn Rate Can Get Out of Control
- SaaStr AI App of the Week: Kintsugi — The AI That Puts Sales Tax on Autopilot
- Dear SaaStr: How Can I Make My Sales Team More Effective?
- 20VC x SaaStr: The $1.4 Trillion IPO Wave Coming in 2026: SpaceX, Anthropic, and Databricks Will Change Everything
- The Real State of Seed Today: The Top 10 Learnings from 50,000 Startups, Per Carta’s Latest Data
- Your B2B New Year’s Resolutions for 2026
- The First $100,000,000 ARR at Samsara: How Founder CEO Sanjit Biswas Built a Platform Giant by Digitizing the Physical World
- Dear SaaStr: What’s The Number One Challenge for Scale-Up Stage Founders?
- What You Can and Really Can’t Replace with AI Today: Sales, Support, CS, and More
- No, Inbound Isn’t Dead. The GTM Playbook Isn’t Broken. But Your Moats Are Shrinking to Months. SaaStr AI London AMA LIVE with Jason Lemkin
- 55% of All Departmental AI Spend Is Now on Coding. And It’s Not Slowing Down
- Want to Get In Front of 3,500 B2B + AI Buyers a Week? Submit Your AI Agent to SaaStr
- Dear SaaStr: How Do I Become a Great Sales Rep?
- The 6 Metrics in OpenAI’s New Enterprise AI Report Worth Knowing — And Why Most of It Is Noise
- How We Use 20+ AI Agents for Marketing & Go-to-Market with SaaStr’s CEO and Chief AI Officer
- Dear SaaStr: I’ve Started to Hate Selling. Would I Be Happier as Sales Manager Instead?
- Why Your Startup Will Fail, If It Does Fail: The Drama Inside, Not Outside
- Dear SaaStr: How Should I Actually Set the Sales Plan for the Year For My VP Sales?
- Dear SaaStr: What Are The 3 Most Important Traits of a B2B Founder?
- 20VC x SaaStr is Back, Live In Person! The TAM Trap: Why SaaS Growth Has Stalled and What AI Changes About Everything
- There’s No Excuse For Sales Qualification Meetings in the Age of AI
- 4 Reasons to Send Investor Updates Even When Times Are Tough
- The Top 10 “Hidden Gem” SaaStr Posts You May Have Missed — Per SaaStr’s Own AI
- Dear SaaStr: How Are VP of Sales Commissions Normally Structured?
- How We Went From 20+ Humans to 3 Humans + 20 AI Agents at SaaStr: More Work, Less Drama, Triple the Output
- Dear SaaStr: For High Dollar Vertical SaaS, Does The VP of Sales Need Domain Expertise?
- The 2026 Sales Reckoning: Why Your Traditional Sales Team Is About To Look Very Different
- Yes, Your VP of Sales Also Has to Be a Great Salesperson Themselves
- Dear SaaStr: What Are The Top 3 Criteria for Hiring Your First Head of Sales?
- AI Agents Catching Other AI Agents Cutting Corners and Hallucinating. And Why That Means AI is Getting So Much Better
- There’s No Excuse for “We’ll Get Back to You in 1 Business Day” in the Age of AI
- Dear SaaStr: How Do I Know If My New VP of Sales is Working Out?
- The 8 Things No One Tells You About ‘Prosumer’ Vibe Coding (That You Need To Learn To Build a Real B2B App)
- Two Billion+ B2B Companies Lost Salesforce Access Indefinitely. This Is Your Security Wake-Up Call.
- PagerDuty Falls to ~$1B Market Cap on $500M ARR. Just 2x ARR. Profitable Isn’t Enough. You Have to Grow.
- Dear SaaStr: I’m at $5m ARR. Should I Hire a CRO?
- The “Buy Your Own Product” Test: Why Every B2B Founder Should Be Their Own Customer (At Least For A Day)
- Our AI SDRs Are Sending 10x More Outbound Emails Than Our Human SDRs — With The Same or Better Results
- The First $100,000,000 ARR at UiPath: How Founder CEO Daniel Dines Went From 10 Years of Struggle to Hypergrowth
- Dear SaaStr: How Many Industry Events a Year Should A Startup Founder Attend?
- How the New SaaStr AI Benchmarking Tool Can Build Your 2026 C60 Plan in Seconds
- The Only 3 Ways to Actually Make Money in B2B AI (And Why “AI-Enhanced” Doesn’t Count Anymore)
- Gartner: Enterprise Software Spend Will Grow a Stunning 15.2% Next Year. But Most Of That Will Go to Price Increases and AI Apps
- Dear SaaStr: I Feel Like I’m Not Getting Enough Done as an Early Stage CEO. What Should I Do?
- Is AI Support Perfect? No. But It’s A Lot Better Than No Support at All
- How Hard It Is to Be a Great VC? Vencap’s Real Hard Numbers from 1,900+ Funds
- Dear SaaStr: How Long Should a CEO Continue Being the Head of Product?
- Our 20+ AI Agents and Their Moats: Real But Weak
- Dear SaaStr: How Much Vacation is Normal for an Early Stage Startup CEO?
- Figma is at $20B. Right Where Adobe Offered to Buy It. When Is Saying ‘No’ Worth It in A Strong M&A Deal?
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