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- 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.
- You’ll Know if That New VP is Going to Fail at the First Board Meeting. Here Are The Clear Tells.
- Dear SaaStr: Should I Use an AI SDR Before I Have a Working Human SDR motion?
- 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
- 5 Interesting Learnings from Cloudflare at $2.8 Billion in Revenue: 36% Growth, a 20% Layoff, and a Stock at 50x Revenue
- Yes, Your CRO / VP of Sales Also Has to Be a Great Salesperson Themselves
- Dear SaaStr: What Should I Look For In My Very First Sales Rep?
- We Run Monaco, Agentforce and Artisan for Outbound. Why We Still Also Built Our Own “AI ABM” Tool for Our Top Accounts
- 10 Crystal Clear Signs Your VP of Sales Just Isn’t Going to Work Out
- Dear SaaStr: My Co-Founder is Threatening to Quit Unless I Give Him More Equity
- 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
- The Problem With Junior Marketing Hires (And What a True VP Costs)
- Dear SaaStr: I’ve Gotten to $1m ARR Selling Myself. What Should I Look For in My First Ever Head of Sales?
- You’ll Probably End Up With 40% Of Your Revenue from “International.” Invest Earlier There.
- What a Great VP Sales Does In Their First Week. Watch For It.
- Dear SaaStr: What Are The Top 10 Metrics For B2B Companies To Track?
- 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.”
- What To Look For In Your First Marketing Hire
- We Vibe Coded Our Own Calendly. Our AI Agent Pushed Us To Do It, and It Was Right.
- 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
- SaaStr AI App of the Week: Chargebee. The Billing System Behind How Gorgias, CodeRabbit, Lambda and Zapier Price AI
- Which to Choose, If You Can Choose, Between Bootstrapping and Raising a Seed Round
- We Got a $240,000 Estimate for Agent API Access. Our Agent Suggested a $5 Postgres Instance.
- Dear SaaStr: How Can I Make Sure My Board Doesn’t Fire Me?
- 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
- 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
- Dear SaaStr: When Should We Start Pushing For Multi-Year Contracts?
- “This Is a Pretty Fancy Dinner. That Probably Means I’m Overpaying.” A Dreamforce Lesson From a Top 5 Customer
- Dear SaaStr: What Should I Do after a Failed Startup? Get a Job or Try Again?
- What 17,000 Subscription Apps Tell Us About Free Trial Length: Annual Plans Convert 86% Better With 30-Day Trials, Monthly Tops Out at Two Weeks, and AI Apps Hit a Wall at 16 Days
- 9 Things Your New Head of Product Should Do in Their First 30 Days
- Dear SaaStr: When Is the Best Time for a Co-Founder to Leave a Startup?
- The Best AI + B2B Events to Sponsor in 2027: Where the Buyers Are
- Almost Every Pre-AI Vendor We Use Is Raising Prices for Agent Access. They May Be Building an Agentic Death Spiral
- Great VPs of Sales Never Hide from a Miss
- Dear SaaStr: Does Freemium Always Work?
- The Irreplaceables. The Employees to Never Let Go. Even If You Have to Invent a Role.
- SaaStr AI App of the Week: Larridin. The Median Engineer Now Bills $213 a Week in AI Coding Tokens. Larridin Tells You What It Bought.
- Dear SaaStr: How Big a Discount Should I Give For Multi-Year Deals?
- Everyone Should Publish the Deepest, Most Direct Competitive Evals They Can. Case Study: $100m ARR Gorgias for AI CX
- I Hired My VP of Marketing at $20k MRR. It Wasn’t a Week Too Early.
- Anthropic Pushes Its $2 Trillion IPO to November, Meta’s Muse Hits #1, and a $40M Seed for a Model That Doesn’t Talk: The Latest 20VC x SaaStr
- 5 Interesting Learnings from GitLab at $1.13 Billion in Revenue: 24% Billings Growth, $20M of Flex in Six Weeks, and 400 Basis Points of AI Margin Cost
- The 30-Day Test: How to Know if Your VP of Sales / CRO Will Succeed
- Dear SaaStr: How Do We Close Bigger Deals?
- Stripe’s AI CRO on the Fastest-Growing AI Companies: 175% Growth, 48% of Revenue From Outside the Home Market, and Agents About to Read More Stripe Docs Than Human
- All Platforms Have Their Favorite Partners. Be One Of Them If You Can.
- Dear SaaStr: When My Startup Raises $10m, Would It Be Appropriate to Take a $170k Salary (no co founders)?
- The SaaStr AI Guide to Building a Top-Tier Inbound AI Agent: 17,000 Conversations, ~600 Meetings Booked, and 60% More New Business
- Why It May Take You 12-18 Months to Hire a Great VP, Sales — Period. And What to Do About It.
- Dear SaaStr: Why Are Pricing Tiers So Effective?
- Being a System of Record Helps With Retention. But Alone, It Won’t Equal Growth
- The #1 Clear Sign a VP Will Fail. Be Honest With Yourself When You See It
- 10 Tips To Get Better at Recruiting. We All Need To.
- Dear SaaStr: Should I Publish My Pricing?
- The New Career Path: Joining a 0% Grower. Maybe For Many, It’s Better.
- The #1 Hack To Making Sure a VP of Sales or Top AE Will Work Out
- Focus Your Marketing Efforts on What Your CMO / VP Marketing is Good At
- 20VC x SaaStr: Pacing the Frontier, Meta Ships Muse And It’s Great, and Miro Sells for $1.35B After a $17.5B Mark
- Dear SaaStr: I’ve Hired 2 SDRs. Can I Hire an AE to Manage Them?
- A Full Teardown of How SaaStr AI Actually Runs Inbound, Renewals, and Outbound on the Latest The Agents
- 10 Things That Would Have Helped Me Go From $1m to $10m Faster with Less Stress
- Dear SaaStr: Why Are VCs So Adamant About Warm Intros?
- What’s Truly “Great” Now in B2B + AI Per ICONIQ? 115% Growth at $100M+, 55% Gross Margins, and $655K in Revenue Per Employee
- 12 Things You’ll Look Back On in B2B … And Regret
- Dear SaaStr: How do VCs Really Feel About Founder Salaries? I Was Told That a General Rule of Thumb is 75% of Market
- 5 Interesting Learnings from ServiceTitan at $1.14 Billion in Revenue: 21% Growth … But a Back Half Guided to Mid-Teens, and a 30% One-Day Stock Price Drop
- Monthly Quotas are Better than Quarterly, At Least Until $10m ARR or So. Here’s Why.
- How to Price Your Product in the Early Days (Hint: It’s Actually Easy)
- We Mentioned Replit in 214 Articles Last Year. For Free. Most Vendors Have No Plan For Customers Like That
- 5 Non-Obvious Things To Know About VCs
- Dear SaaStr: Should I Cap Commissions of My Top Salespeople? They Make So Much
- What Would an Independent Slack Look Like If It Hadn’t Sold to Salesforce? And Would It Still Be Worth $27 Billion?
- The First Week of a Great VP of Sales. And The First Month of a Mediocre One.
- The CEO Never Gets to Step Away From Sales
- We Run 21 AI Agents and They’ve Closed Millions. But There Still Isn’t a Good AI Account Executive. Yet
- Why You Should Kill Your Competitor in B2B
- Dear SaaStr: When Should a Startup Hire its First Sales Person, and What Should Their Profile Look Like?
- Harvey Puts a Former Practicing Lawyer in Every Deployment. About 180 of Them. Here’s How That Model Works
- SaaStr AI App of the Week: Sumble. The Kaggle Founders Rebuilt Sales Intelligence Around Context, Not Contacts
- Dear SaaStr: What’s a Good Benchmark for B2B Sales Cycles?
- Is the Era of the Sales-Guy CEO … Over in B2B?
- Of Course Your Competitor Is Trying to Sell To, And Steal, Your Customers and Prospects
- Dear SaaStr: What Are The Benefits and Drawbacks of Having co-CEOs?
- One Thing Miro + Airtable Show: Getting Cash Flow Positive Isn’t Magical
- Before You Start as a VP — Please, Please, Please. Do a 60-Day Plan. And Make Sure the CEO Agrees With It.
- Dear SaaStr: What’s a Fair Amount of Founder Secondary in a Series B VC funding round?
- 20VC x SaaStr: Jensen Declares AGI, $170M of Secondary Before the Series C, and Why Index Walked Away From Town
- 5 Interesting Learnings from Snowflake at $6 Billion in Revenue: 37% Growth and Accelerating, 126% NRR, and a Gross Margin Guided Down to Pay for AI
- The 3 Financial Plans You Need for The Year: C-90, C-60 and C-10 (Updated)
- Dear SaaStr: Should You Ask a Prospect What Competitors They Are Looking At?
- ElevenLabs Went From $0 to $600M+ ARR in 41 Months. When the AI Agent Closes the Deal, They Still Pay the Human. With Carles Reina, First VP of Revenue
- What VCs Are Looking For Now: $25B+ Exits. The New “Decacorn”
- Dear SaaStr: If I Whitelabel My B2B Product, Will it Hurt Me on Branding?
- Meet Our Agents: What All 20 Actually Do, What They Refuse to Do, and Every Place They’ve Failed Us
- Champion Change: You Gotta Jump On It
- Dear SaaStr: How Long Should You Give a New Sales Rep?
- Founders Are Coming Back to Run Their Pre-AI B2B Companies. Because It’s The Last Stand.
- Don’t Hire a CRO / VP of Sales Everybody Loves
- Dear SaaStr: As a Founder, What Will I Learn Getting More Involved in Sales?
- Jason’s Takes on This Week’s 20VC: Locks Beat Guardrails, Agents Pick Your Software, and Building With 448 Open Tasks
- Beyond the SaaSpocalypse: The Winners and Losers of 2026 (So Far)
- Dear SaaStr: I’ve Got 4 Sales Reps. Should My VP of Sales Have Their Own Quota?
- California Is Taxing SaaS and AI Tools and Is About to Make Your Software 8-10% More Expensive. Here’s What SB 122 Does to Buyers and Vendors
- No, Free Pilots and Free Trials Aren’t Revenue. Keep it Simple — And Real.
- 20VC x SaaStr: Nvidia Guides to 70% Growth, 1,000 Agents Breach Hugging Face, and Clay at $7B
- Goodnight & Goodbye, SVB
- The Top 10 Mistakes Folks Make Hiring Their First Sales Team (Updated)
- Dear SaaStr: Why Do Enterprise Customers Insist on Pilots?
- 5 Interesting Learnings from Salesforce at $45 Billion ARR: 14% cRPO Growth, 6% Organic Growth, and $2.53 of EPS From Its Anthropic Stake
- After $2m in ARR — Start Specializing Your Sales Team
- Dear SaaStr: What Do You Have to Get Right in a Start-Up?
- The CPOs of Harvey, Glean and Rubrik on What It Actually Takes To Ship a Category-Winning Agent
- Our Newest AI Agent Is a Renewal Agent. It Builds a Better Renewal Deck Than Any Human Could, For Every Single Account. Not Just the Big Ones.
- In The Early Days, You Won’t Have Enough Customers. But Your Mini-Brand Will Come to Your Rescue.
- Dear SaaStr: What’s the #1 Way I Can Accelerate My Career Growth?
- ICONIQ: The 100%+ Growers Added 133% More Headcount in H1 2026. But The 50%-100% Growers Cut Hiring Almost in Half.
- To Really Scale, You Need $1M on Your Balance Sheet for Every $2M in ARR
- Dear SaaStr: What’s the #1 Reason You See Sales Reps Fail These Days?
- We’ve Been Running Salesforce Headless for 6 Months on Our Own “Claudeforce.” We’re Never Going Back
- 10 Things That Tell a VC You May Not Be Ready for “Prime Time”
- Dear SaaStr: My Sales Rep is Grossly Underperforming but is Involved in a Key Deal. Should I Fire Him or Wait for The Deal to Close?
- Owner.com Did an AI Rebuild to Accelerate Past $100M ARR. The 7 Top Lessons, and What It Takes to Copy Them
- What Differentiates The Best Founders? They Really, Really Know Their Stuff
- Dear SaaStr: Should I Send My Pitch Deck to Any VC Who Asks for One?
- Rule of 40 Is Half Dead: Growth Is All That Matters, Margins Above 25% Don’t Help, and Category Beats Both. The Latest From Kroll
- You’ll Lose Customers. It Hurts. But Don’t Let Them Become Angry Ex-Customers.
- Dear SaaStr: What’s The Best Way to Fire Your Co-Founder … Who Was Once a Friend?
- When Agents Take Over the System of Record: 40GB Nobody Typed, a Renewal Agent Built in Half a Day, and Why Our Agents Love Clay: The Agents #013
- 50% of the Work Created in Linear Is Now Created by Agents. A Year Ago It Was 3%.
- If the CRO / VP of Sales Doesn’t Believe, It’s All Over. You Both Just Need to Move On
- Dear SaaStr: Should I Do a Dinner or a Booth at a Big Industry Event? Or Just Buy Tickets?
- 20VC x SaaStr: Nvidia Pays $6B for Poolside’s Model Factory, OpenAI Has to Go Public in 2027, and Why $9B No Longer Clears the Bar for Seed
- Only 7 Public B2B Companies Are Growing Over 30%. In the AI-Native Cohort, That Would Be Last Place
- Dear SaaStr: What Are Some Signs That Your B2B Marketing Programs Won’t Scale Well?
- Dear SaaStr: When a VP Sales is Struggling, What Do They Start to Do That … They Shouldn’t?
- A Quiet Salute to the CEOs Still Rebuilding for the Age of AI. Most Are Maybe 40% Of The Way There.
- 5 Interesting Learnings from Box at $1.29 Billion in Revenue: 17% Billings Growth, 106% NRR, and 20 Basis Points of AI Margin Cost
- Dear SaaStr: Why Do Many Startup CEOs Quit After Their Companies Are Acquired?
- The 3 New Pricing Models in B2B. Pick One, Because The Old One (Just Seats) Really is Dying
- The Best CROs and VPs of Sales Make Their B Team Shine
- Dear SaaStr: How Does a Sales Rep Truly Add Value?
- BigCommerce vs. Shopify: When Second Place Is a Very Tough Place to Be
- The Top 5 Reasons I See CROs Flame Out
- Dear SaaStr: How Long is a Venture Round Supposed to Last?
- Stripe Buys OpenRouter for $7B, Anthropic Turns Its First Profit, and Silver Lake Circles Workday at $43B: 20VC x SaaStr
- Dear SaaStr: Growth Has Slowed and My VP of Sales is Pushing Me To Hire More Reps. Is That The Right Way to Go?
- Everyone Ends Up With a Sales Team. Even in the AI Era. The Team Just Scales Later Now. See, E.g., Replit, Gamma, Lovable, Anthropic, etc.
- A Simple 4 Part Test to Know If You’ve Hired the Right VP
- ServiceTitan Just Shut Off Podium’s Integration for ~1,000 Shared Customers. Why? Agents Turned a 9-Year Partner Into a Direct Competitor.
- Dear SaaStr: How Do You Build a Real Exit Strategy?
- Vertical B2B Leader Owner Acclerated After $100M ARR With Agents. The Key Insight: Every Time a Customer Logs In, Owner Has Failed.
- Top 10 Mistakes I See New CROs and VP Sales Make The First Week on the Job
- Dear SaaStr: Can A Great Sales Rep Sell Any Product?
- 5 Interesting Learnings from Atlassian at $6.6 Billion in ARR: 28% Growth, 44% RPO Growth, and a 35% One-Day Stock Pop
- 9 Tips To Closing More Bigger Deals
- Dear SaaStr: One of Our Most Respected Team Members Quit and Folks Are Leaving. What Do I Do?
- Rippling Ran 2,100 Scored Agent Runs Per Model on Real Payroll Data. The Cheapest Model Tied the Most Expensive One.
- On Your Next Big Deal? Double Your Pricing.
- Dear SaaStr: I Was Fired Without Cause. Should I Tell My Story Publicly?
- We Churned Notion After 7 Years. Our AI Agent Took Its Last Job.
- Dear SaaStr: How Can I Become a Better VP of Sales?
- Jason’s Takes on This Week’s 20VC x SaaStr: The Agents Never Suggested Canva, The Meme You Can’t Outrun, and Why I Only Underwrite Founders Now
- The 0% Quota Club (And Why the Same Mediocre Rep Hits 70% at One Company and 0% at Yours)
- Dear SaaStr: The CEO of Our Competitor Wants to Meet – What Should I Do?
- Gamma’s CEO: Why Getting to $100M ARR Without A Sales Team Worked. And Why It Was a Mistake.
- Dear SaaStr: What’s Your #1 Opener in Sales?
- Klaviyo’s CEO on Building at $1.5B With Agents: “Dark Factory,” Composer, and Why Every Single Employee Had to Hit L3 by June
- Databricks Just Crossed $7B ARR Growing 80% (!): A 30-Point Acceleration, a $190B Valuation, and the Margin Bill for Agents
- Canva Cuts 2026 Growth by a Third, Jeff Dean Walks Out of Google, and Elon Builds His Own Fab: 20VC x SaaStr
- B2B For Physical Products Is Crushing It: Shopify +34%, Toast +23%, Samsara +30%
- Dear SaaStr: At What ACV Size Do I Need an Account Manager in B2B?
- Beware the “Mediocre Recycled.” The Zombie Executives of B2B + AI.
- A Checklist: 10 Signs You Shouldn’t Hire a Sales Rep
- 5 Interesting Learnings from Palo Alto Networks at $11.4 Billion in Revenue: 60% ARR Growth, 120% NRR, and a $25B Acquisition That Doubled the Stock
- 90%-95% of Salespeople Won’t Make It At Your Startup. A 6 Part Test to Help You Get It Right.
- Pylon’s Founders at SaaStr AI Day: How Its Support Team Deflected 50% of Tickets Without Increasing Headcount
- How Mailchimp Went From $1B+ ARR to … Shrinking Inside Intuit. A Death Spiral in the Age of AI?
- When You Hire Your First Sales Rep — Just Make Sure You Hire Two
- Atlassian Just Deleted Loom’s Free Creator Seats. They Were Also Loom’s Distribution.
- Dear SaaStr: What Is A Good Demo Conversion Rate for a SaaS Startup?
- The Simple Math Behind a 3x Venture Fund: Why Your Best Investment Needs to Return the Whole Thing
- Backstory Retiered Its Entire Customer Base in 3 Days. The Same Exercise Used to Take Five Teams a Quarter.
- 5 Interesting Learnings from Shopify at $14B in Revenue: 34% Growth, 18% Free Cash Flow Margins, and AI Orders Up 3x
- If You Don’t Think You Need a VP of Product, VP of Marketing, Etc. — Then You Haven’t Worked With a Great One
- I Bought 30+ APIs This Year. Only Exa Asked How It Went. Copy Them.
- 10 Things That Always Work in B2B Marketing
- Hire the Right Type of VP Marketing — Or You’ll Just End Up With a Bunch of Blue Pens with Your Logo On Them (Updated)
- “Our AI Agent Rewrote Our App Without Telling Us” The Agents #12 is Here!
- Airtable Just Sold for $2.25B at 2.7x ARR. It Raised $1.4B and Was Once Worth $11.7B. This Was … Market
- Dear SaaStr: How Do You Compensate Reps on Multi-Year Deals?
- 5 Interesting Learnings from Palantir at $7.7 Billion ARR: 93% Growth (!), 157% NRR, and a Rule of 40 Score of 155%
- 12 of the Most Common Mistakes Scaling Your First Sales Team
- Nue’s Guided Selling Playbook Took 2 Minutes to Build. The Full Implementation Still Takes 90 Days.
- I Was Wrong About Marketing ROI. Here’s What $100,000,000+ in Sponsorship Sales Taught Me.
- 2026 Is The Biggest IPO Year In History. But Take Out SpaceX And Right Now It’s One of the Worst.
- The AI Board Member: Should Yours Should “Chair” the Next Meeting? At Least Conceptually
- Jason’s Takes on This Week’s 20VC: The Toggle Is a Permission Grant, The Blame Test Decides the Deal, and Why Five Years of Price Increases Is a Countdown
- The #1 Most Important Thing to Understand About AI SDRs: They Can’t Figure It Out For You. That’s Still Your Job. For Now, At Least.
- Dear SaaStr: I Fired My VP of Sales. What Now?
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