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- Did Windsurf Sell Too Cheap? The Wild 72-Hour Saga and AI Coding Valuations
- Who Should Marketing Report To? What 3,000+ Companies Actually Do (And Why It Matters)
- The Real Work of AI: Why Human-in-the-Loop and Orchestration Are Bigger Jobs Than You Think
- 11 Signs To Predict If a Venture Investment Will or Won’t Work Out
- Aaron Levie Box’s CEO: The Great AI Acceleration: Why No Position Is Safe (And That’s Good News)
- The Early Days: 5 Things Vanta Got Right, And 5 It Got Wrong, Getting to First $10m ARR
- How Anthropic Rocketed to $4B ARR — And Why Your B2B Playbook May Already Be Obsolete
- Vibe Coding is the Future. But “Roll Your Own?” That’s More Complicated.
- Dear SaaStr: My Customer Hasn’t Paid. When is it Worth it to Hire a Collections Agency?
- Anthropic May Never Catch OpenAI. But It’s Already 40% as Big.
- Cursor: Our Users Love Per Seat Pricing. It’s Just The Cost Side Makes It Harder.
- AI-Native GTM Teams Run 38% Leaner: The New Normal?
- We Thought These Leads Were Dead. Our AI Proved Us Wrong (And Booked 4 Meetings in 48 Hours)
- AI and the Bottom Line with Canva’s CCO: How They Built a $7B Enterprise Motion on 16 Billion AI Interactions
- SaaStr AI App of the Week: Syllable.ai
- Dear SaaStr: What Are The Top Worries Founders Have As They Start to Scale?
- The Latest 20VC + SaaStr: Meta’s $1B Talent Raid, the End of Triple-Triple-Double-Double, and Why AI Laggards Are Getting Left Behind
- Olo vs Toast: $2B vs $25B – The Strategic Tale of Two Tech Giants
- We Sent 4,495 AI SDR Emails in 2 Weeks and Got The #1 Response Rate. Here’s How (It’s Not What You Think)”
- Dear SaaStr: What Does the Day-to-Day Look Like For a Customer Success Manager?
- NVIDIA Hits $4 Trillion: What Founders Can Learn from the Greatest Growth Story Ever Told
- Only 11% of Unicorn Exits Are IPOs Now (Down from 53%)
- Sales In The Age of AI: The Playbook from The CROs of Databricks, Windsurf, Perplexity and Owner
- 5 Interesting Learnings from SEMRush at $425,000,000 in ARR
- Dear SaaStr: At $20,000 ACV, How Many Customers Should Each Customer Success Manager Have?
- Canva Is Giving Its 5,000 Employees a Week to Learn AI. Will It Work?
- 88% of B2B IPOs Have Founder CEOs. And Those Ones Do Far, Far Better
- From AI Billions to Sales Struggles: The Top 10 SaaStr Posts of The First Half of 2025
- Dear SaaStr: How Do You Best Pick and Choose Board Members and Senior Advisors?
- Palantir’s +79% vs Bill’s -43%: The AI Divide That Defined SaaS Performance in 1H’25
- VC Dollars Are Up, Yes. But VC Rounds? They Are At a 7+ Year Low
- Webinars Almost Always Work. If You Really Commit. Start Next Week.
- Dear SaaStr: What Are The Top Mistakes Managers Make In Startups?
- NFDG: The $1.1B VC Fund That 4X’d in Two Years—Then Got Acquired by Meta
- Top 10 Interesting Learnings From Figma’s IPO … That You May Have Missed
- Yes Customer Testimonials — Done Right — Are Super Important
- Dear SaaStr: How Do I Hire a Great VP of Sales?
- It’s Not Just You. Lead VCs Are Taking More of Each Round
- The Early Days: How Veeva Hit $100m ARR With Just $3m Raised — And a Deep Vertical Focus
- Dear SaaStr: How Should I Calculate Gross Dollar Retention For Our Investors?
- PE Loves SaaS Again: Thoma Bravo Buys Olo for $2 Billion
- The Vertical SaaS Gold Rush: Why Non-Tech B2B Is Growing 250%+ Faster
- AI Agents in B2B: Top 10 Learnings from Aaron Levie, CEO of Box and IBM’s VP of AI
- The Latest 20VC + SaaStr: Rule of 80, 9-Figure Zombies, and the Death of Predictable Venture Math
- The Surprising Enterprise AI Giants: Oracle and SAP (Really!)
- How to Handle, and Share, Bad News
- SaaStr Live: How Wiz’s CMO Built a $32B Marketing Machine (Without Any Marketing Experience)
- Microsoft: We Need A Lot Less Employees. And a Lot More AI Infrastructure.
- What’s Accelerating in 2025: $5B+ Unicorns
- 7 Changes You Can Make Today To Grow Faster
- Dear SaaStr: How Do I Ramp a New Sales Rep at a Seed Stage Start-Up?
- 5 Interesting Learnings From Figma at $900,000,000+ ARR. The B2B IPO of The Year?
- What 300 of The Highest Growth B2B Startups Are Actually Doing With AI: The Latest from ICONIQ
- Everything Now is Just So Much Faster in The AI Age. Have You Adjusted?
- Why AI Has Taken Longer to Come to Sales Than Coding with Artisan’s CEO
- Dear SaaStr: I’m Joining a Start-Up as Head of Sales At Just $1m ARR. What Should I Do First?
- Salesforce, Microsoft, Google and Atlassian All Raise Prices Again in 2025. Hooray.
- AI Apps The SaaStr Team Loves — and Uses Every Day
- The Confounding Logic of Discounting
- Yes, Open AI Has Raised an Insane Amount of Money. But It Tracks Insane Growth Almost 1:1
- Dear SaaStr: How Should Startup Founders Approach Early-Stage Hiring?
- The Early Days: How Deel Went From $1m to $100m ARR in Just 20 Months
- How AI Led Palantir From Slow Growth (13%) to Hypergrowth (49%!)
- 10 Marketing Tactics That Always Work for Early-Stage SaaS StartUps
- Dear SaaStr: How Should Founders Build Their First Customer Success Team?
- 7 Of The Biggest Mistakes First-Time Founders Make. And How They Can Be Avoided.
- IPO Offerings Are Already Up 62.5% This Year. With Much More to Come. We’re Back
- Dear SaaStr: What Are The Rough Benchmarks for Raising a Series A?
- Sink or Swim: Every Enterprise Conversation is AI Today. And Every Enterprise AI is Different.
- 10 Brutal Truths From Coatue About AI and Who Gets Left Behind: The Great Separation
- The Great AI Talent Grab: The Latest 20VC with Jason, Harry and Rory
- AI Won’t Replace Sales Reps So Much as ‘Deflect’ Them: What Support’s 70% Deflection Rates Tell Us About Sales’ Future
- At Least 20% of Your New Customers Should Come from Referrals and Word of Mouth. Ideally, 50%.
- AI and Cybersecurity: How Rubrik’s Co-Founder Built a $1B+ ARR Platform While Joining the AI Revolution
- Wealthfront Files to IPO at $340,000,000+ ARR. IPOs are Back!
- VPs That Can’t Hire … They Aren’t Real VPs. At Least, Not Yet.
- M&A Is Back! Melio’s $2.5B Exit to Xero — In Just 7 Years!
- Dear SaaStr: What is a Normal Commission for an Account Exec as a Percentage on Revenue of a Deal?
- GTM in The Age of AI: The Top 10 Learnings from ICONIQ’s 2025 B2B SaaS Report
- Why Mergers & Acquisitions Are Weird and Unpredictable
- Dear SaaStr: How Much Equity is Typically Given Out to the First 50 Employees?
- From $10M to $100M ARR in 5.5 Months: Inside Replit’s AI Coding Rocketship
- If Your Team Hasn’t Rolled Out Truly Great AI Into Production Yet… It’s Time to Reboot the Team
- Sometimes All Your Bigger Customers Want is Just To Be Heard
- The Great SDR Downsizing: 36% of B2B Companies Cut Sales Development Teams in 2025
- Dear SaaStr: My CAC Has Doubled Over The Last Year. Should I Stop Hiring?
- Navan Files for IPO: The Opening of B2B IPO Floodgates?
- How Long It Roughly Takes to Close a Deal in SaaS. And Why.
- How 1,000+ B2B Startups Are — And Aren’t — Growing. The Real Data.
- How The Top 25 B2B Public Companies Have Performed In 2025 So Far — And What They Tell Us About the Future
- Outbound Always Works. If You Do It Right. And You Put In The Time.
- Dear SaaStr: What Should I Know As a First-Time Customer Success Manager?
- The $14.8B AI Deal That “Makes No Sense,” IPO Pops, and Why Legacy B2B is Stuggling: The Latest SaaStr + 20VC Breakdown
- The $939B Question: Is AI Eating SaaS or Feeding It?
- Dear SaaStr: I Just Sold My Business for $130M. Should I Stick Around?
- Welcome Back Duplo Cloud & Pylon to SaaStr Annual 2026! 🎉
- The Top 3 Reasons AI Sales Tools “Don’t Work” (Spoiler: They Actually Do)
- The $4.5B Board Meeting: Inside Snowflake’s AI Transformation and the CEO Who Bets His Company on Their Platform
- Dear SaaStr: How Do I Get a Job as a First Time VP of Sales?
- 5 Interesting Learnings from Okta at $2.75 Billion in ARR
- 10 Ways to Build a Moat in SaaS. But AI is Also Making Them Weaker.
- Only 37% of 2019 VC Funds Have Returned Capital: Inside the Numbers That Show Why VC Fundraising Has Gotten So Hard
- Dear SaaStr: Should I Hire a Sales Consultant as My First Sales Rep?
- AI-Native Companies Are Creating a New Performance Tier: 132% NDR, 100% Growth at Scale, and 56% R&D Investment That’s Leaving Everyone Else Behind
- ChatGPT Is Becoming the Ultimate Mega-App: And It’s Already Starting To Eat B2B Software
- Dear SaaStr: What Are Some Tips For Shortening Enterprise Sales Cycles?
- Databricks Just Caught Snowflake at $3.7B ARR. Here’s How They Did It (And What’s Next)
- AI is Already Increasing Our Cognitive Load. That’s Only Going to Increase — Dramatically.
- A16Z: Enterprise AI Spending is Growing 75% a Year.
- Dear SaaStr: How Often Does a Typical SDR Follow Up With a Prospect? Probably Too Often These Days
- MCP and The Fight Over Whose Data it is: The Coming Enterprise Software Revolt
- Eventually … Almost Everyone Has a Sales Team
- Dear SaaStr: How Do I Make Sure My First 1-2 Sales Reps Are Strong?
- SaaStr on 20VC This Week: Why 40% Cloud Adoption Marks the End of Easy Growth. And Why the AI Budget War is Just Getting Started
- Before You Start as a VP — Please, Please, Please. Do a 60-Day Plan. And Make Sure the CEO Agrees With It.
- The ChatGPT Moment: When 8 Years of Growth Happens in 8 Months
- Dear SaaStr: Should I Let My VP of Sales Go? I’m Not Sure I’ve Made The Right Hire
- Dear SaaStr: How Do You Balance Optimism with Realism When Pitching VCs?
- The VP of AI Trap: Why Hiring One Exec Won’t Transform Your Company. In Fact, It May Make It Worse.
- A16Z: The Median Enterprise AI Startup now Hits $2.1M ARR by Month 12
- Dear SaaStr: What Are Some Interview Questions a CEO Can Ask an Account Executive?
- 5 Ways AI Has Already Changed SaaS Sales Forever with Perplexity’s CBO Dmitry Shevelenko and SaaStr CRO Confidential Host Sam Blond
- Why Every B2B Software Company is About to Become a Backend Service. You Need To Get Ahead Of It.
- CMO Budgets Are Flat for 3+ Years. But 99% of CMOs Say Gen AI is a Top Priority.
- Dear SaaStr: When Should I Hire My First AE?
- 5 Interesting Learnings from Circle at $2.3 Billion in “ARR”
- Every Month is a Good Month to Raise: What 42,000+ Funding Rounds Tell Us About Raising Capital in July
- Dear SaaStr: How Does a Founder Mindset Change As You Go From Startup to Scaleup?
- The Hidden Truth About Vibe Coding in SaaS: Most B2B Software Was Never Hard to Build
- The Private Equity Hangover: What B2B Founders Need to Know About the $3.6T Exit Logjam
- Dear SaaStr: We’re at $8m ARR, Growing 50% and Bootstrapped. Should We Raise a Growth Round?
- The Great IPO Awakening: What 2025’s Surprisingly Hot Market Means for B2B Companies
- Stealth AI Churn: Are Your Customers Starting to Leave Already?
- The HubSpot AI Playbook: How Yamini Rangan Is Leading the Most Aggressive B2B AI Transformation
- Dear SaaStr: What is The Best Way to Set Sales Rep Quotas at Each Stage of a B2B Business?
- Top SaaStr Posts and Vids of the Week: The AI Database Wars, Why YC is on Fire, and a 50% AI Sales Team
- The “AI Slow Roll” is Killing Your SaaS, Why Existential Dread is Needed Today: The Latest 20VC with Rory, Harry + Jason
- Is AI Penetration … Slowing Down? Ramp Says Possibly
- Dear SaaStr: We Have More Than 20% Churn Our First Month. What Should We Do?
- SaaStr AI is Heading to London, 1-2 December!
- SaaS Is Still Slowing Down, Unfortunately: What Q1 2025 Numbers Reveal About the Cloud Software Market
- 🚀 Top 5 SaaStr Learnings from G2’s 2025 Buyer Behavior Report: You Gotta Be AI
- Dear SaaStr: Should I Move My Start-Up to SF Bay Area?
- The Death of “AI Won’t Touch Enterprise Sales”: How ChatGPT’s Record Mode Is The Start of Everything Changing
- Why Racing to $100M ARR Doesn’t Actually Predict Generational Outcomes from Scale Venture Partners
- How The Smartest Founders Are Already Winning with AI: SaaStr on My First Million Podcast
- The New Rules of AI Investing: Why Speed Beats Strategy and Labor Budget Is the New Software Budget with Google Cloud’s COO
- Dear SaaStr: What Are A Few Top Tips to Hiring The Right First VP of Sales?
- 5 Interesting Learnings from Chime at $2 Billion in ARR
- The 40% Problem: Do Your Sales Reps Really Cover All Their Accounts? And Is AI The Answer? With Yamini Rangan, CEO HubSpot
- Dear SaaStr: Can I Buy Out My Seed VCs? We’re Doing Well But We’re Not on Venture Path Anymore
- Thoma Bravo’s Record $34.4B Fundraise: Great News for B2B and SaaS Founders
- Gartner: Only 18% of CROs and 15% of CMOs are considered “AI-savvy” by their own CEOs.
- In The Age of AI, It Just Won’t Be Enough Just To Be a “Good People Person” in Sales
- Dear SaaStr: What Are Good Benchmarks for Sales Productivity in SaaS?
- Snowflake Buys Crunchy Data for $250m, Databricks Buys Neon for $1B. The New AI Database Battle.
- AI Startups Burn Through Cash 2x as Fast, and 10 Other Top Learnings from SVB’s Latest in Enterprise
- Top SaaStr Posts and Pods of the Week: The Great AI Reset, Marc Benioff on M&A and AI,
- The Top 10 SaaStr Learnings from Mary Meeker’s Latest Report on AI
- Dear SaaStr: What Are The Most Common Mistakes First-Time Founders Make Building Enterprise Sales Teams?
- The Latest SaaStr + 20VC: The Brutal Math of Venture Capital — What Every B2B Founder Needs to Know
- Dear SaaStr: How Much Equity Do You Give to Employees at Different Stages of Growth?
- 15 Questions VPs of Sales Should Ask CEOs. Before They Take That Job.
- The Great ARR Acceleration: Q1’25 Numbers Tell the Comeback Story
- Dear SaaStr: How Should I Think About Family and Balance If I Want to Build Something Big?
- AI, Sales + GTM in 2025/2026: This Changes Everything with Jason Lemkin and Owner CRO Kyle Norton
- The Bay Area Has 54% of All SaaS Funding. Everyone Else Isn’t Even Close.
- Dear SaaStr: We’re Starting a Big Paid Pilot. How Do Maximize the Chances of Success?
- 5 Interesting Learnings From Monday at $1.125 Billion in ARR
- MNTN and Hinge Health IPOs: No, You Don’t Need $500m ARR to IPO. But You Do Need ~50%+ Growth
- Dear SaaStr: What’s the Best Way to Build a Comp Plan for Account Managers Focused on Upsell?
- The Wild Ride of Informatica: 32 Years, 2 IPOs, to $8 Billion Acquisition by Salesforce
- 8 Out of 10 SaaS Founders Are Burning Cash Faster Than Ever — And Why YC is On Fire (SVB’s 2025 Data Breakdown)
- In The Age of AI, Onboarding and Time-to-Value Should Be The #1 Goal for Customer Success
- The 2026 Sales Team: 50% Humans, 50% AIs. All 1 Team.
- Perplexity’s CBO: Speed is The New Moat in AI Sales
- Dear SaaStr: Our Champion Left The Company. How Do I Ensure a Shaky Deal Doesn’t Collapse?
- Dear SaaStr: When Is It “Too Early” To Hire Your First Marketer?
- Top SaaStr Post of the Week: The Great AI Reset, OpenAI to Hit $12.7 Billion in Revenue, The 250,000 Customer Club
- 3 Ways I’ve Changed Venture Investing at SaaStr Fund
- Dear SaaStr: We Have a Ton of VC Interest But Are Profitable. Should We Still Raise?
- The Top 10 Strategies Toast’s CRO Uses to Crush Quotas
- The Latest SaaStr on 20VC: The State of SaaS 2025: IPOs, AI, and the Coming Shakeout
- How SaaStr Fund-Backed RevenueCat Went from a $1.5M Round at $7M Valuation in 2018 to $500M+ Today
- Dear SaaStr: What Is It Like … After Your Startup is Acquired?
- The AI Wake-Up Call with Jason Lemkin: Why You Need to Move Faster or Get Left Behind
- Dear SaaStr: How Can I Crush a VP of Sales Interview?
- 5 Interesting Learnings from Palantir at $3.5 Billion in ARR
- The 250,000 Customer Club: How HubSpot and Monday.com Both Created SMB+ Empires
- Dear SaaStr: What Are The Top 10 Metrics For SaaS Companies To Track?
- AI Adoption: 5 Hard Truths About the Fastest Technology Transformation in History With Aaron Levie, CEO Box
- The Great AI Reset: It’s Time to Refound Your Start-Up. Now.
- Dear SaaStr: We’re Thinking of Bringing in an Outside CEO to Help Us Scale. How Much Should We Pay Them?
- The Reality of Selling Your Company: What No One Tells Founders with Brian Halligan, Co-Founder and Chair of HubSpot
- Are You Fundable Today? Just Ask Your Existing Investors. Just Ask Them.
- The Bar Today for a Series B
- Dear SaaStr: I’ve Got 4 Sales Reps. Should My VP of Sales Have Their Own Quota?
- New SaaStr on 20VC! “The VC Playbook: What’s Working in 2025”
- Our CAC is Way Too High. Should We Cut Marketing To The Bone?
- Dear SaaStr: What Are Some Red Flags an Investor Might Not Be Serious?
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