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- 5 Interesting Learnings from Snowflake at ~$4 Billion in ARR
- CRO Confidential: How Windsurf Built A Billion-Dollar AI Company and a Winning Sales Machine with VP of Worldwide Sales, Graham Moreno
- The 10-Point Checklist For When You Sell Your Company With Founder Collective
- Egnyte Sells to Private Equity for $1.5 Billion after 18 Years. Slightly Slower and Steady Wins, Too.
- Dear SaaStr: What Are Great Examples of Fast Follower Companies That Become Market Leaders?
- The Per-Seat Model Isn’t Dead. But Also, Surprisingly, It Was Never Dominant.
- The Top Product Roadblocks and Headaches Scaling from $0 to the First $100M ARR with Neo4j CTO Philip Rathle
- The Top 5 Challenges in Starting a Successful SaaS Company. And 5 Things That Don’t Matter As Much As Many Think.
- The Revenue Playbook: Rippling’s Top 3 Growth Tactics at Scale with Rippling CRO Matt Plank and Sam Blond
- Top SaaStr Posts and Pods of the Week: CEO Procore, AI at Monday.com, CRO Databricks and More!!
- Dear SaaStr: What’s The Hardest Part About SaaS Companies, At Each Stage?
- Where Are The 2021 Unicorns Today? 60% Are Stuck In Limbo, Per Carta
- CEO Systems: 5 Key Lessons for Scaling Through Every Growth Phase with HashiCorp CEO Dave McJannet
- Dear SaaStr: What’s The Best Way to Improve Email Response Rates?
- NEW SaaStr Annual Speakers! CEO Gitlab, CEO + CTO Gusto, CBO Perplexity and More
- AI at Scale: 8 Learnings from monday.com Co-Founder and Co-Ceo Eran Zinman
- Salesforce: We Are Hiring 0 Engineers This Year. But We’re Growing The Sales Team +20%. Because AI.
- We’ve Got 1,000 No-Cost VIP SaaStr Annual Tickets In Our Inclusion Program. Apply Now!!
- This is Probably The Last Chance for the “Lost Generation” of SaaS and B2B
- 5 Interesting Learnings from Salesforce at $40 Billion in ARR
- Are You Really On The IPO Track? If Not, Maybe Don’t Unicorn
- The Journey from Freemium to PLG to SLG: Key Learnings from Dropbox, Salesforce and Vimeo
- Dear SaaStr: Should SaaS Startups Really Have CROs or COOs? Is That Too Many Management Layers?
- The Top 10 Reasons to Attend 2025 SaaStr Annual, May 13-15 in SF Bay!!
- The 2021 GTM Playbook Is Mostly Dead. But What’s The AI Era Replacement?
- Dear SaaStr: How Do You Know When it’s Time to “Fire Yourself” as a Founder?
- Sapphire Ventures: VC Deals in B2B Start 2025 … Down Another -8%
- Top 10 Learnings On What Getting Acquired is Really Like From Ex-Head of M&A at Own, Rackspace, NetApp and Yahoo!
- Dear SaaStr: What Are The Pros and Cons of Selling Your Company?
- The New Playbook for SaaS Customer Stickiness: 5 Key Lessons from Prismatic’s Revenue Leaders
- The Top SaaStr Posts and Pods of the Week: Procore’s CEO, Databrick’s CRO, Stripe’s CBO, Tunguz + Lemkin on AI in B2B
- Dear SaaStr: What’s a Good Example of a Monthly Investor Update?
- What to Do When a BigCo Says They Want to “Build, Buy or Partner”
- Dear SaaStr: What Are Some Things That Make a Founder Look Naive to VCs?
- How Much More Should Your Sales Team Do … Than Just Plain Selling?
- Want To Do a Podcast? More B2B Content? Build More of an Audience? Here’s My #1 Tip
- The #1 Event for SaaS and Business Software: SaaStr Annual
- The Real Story Behind B2B SaaS Growth Today: What Maxio’s Data from 2,400+ Private Companies Tell Us
- Who Is Tooey Couremanche Founder and CEO of Procore
- Incredbile New Speakers for SaaStr Annual and SaaStr.ai Summit 2025! CEOs Calendly and Bolt; CRO ServiceTitan; CBO Perplexity and Much More!
- How AI is Really Changing SaaS From the CEO of Procore, co-CEO of Monday and Chair of HubSpot
- Dear SaaStr: How Many Sales Reps Do I Need?
- The 2025 SaaS Vibe Check: What Founders Need to Know Right Now with SaaStr CEO and Founder Jason Lemkin
- 5 Interesting Learnings from Similarweb at $260,000,000 ARR
- The Only 3 Customer Success Metrics That Actually Matter for Building a $100M ARR Business with ChurnZero’s CEO
- Get Funded or Just Learn: VC Day at SaaStr Annual 2025 (!!). May 15 in SF Bay!!
- The Real Data on What it Takes to Go Big and Eventually IPO with Meritech Capital
- Dear SaaStr: When Should You Hire Your First Demand Generation Marketer in SaaS?
- One Way to Hit 50% Growth at $250,000,000 in ARR: Merge With Another Start-Up
- Is The Only Way to Get a Good Deal on a Renewal … To Threaten to Leave?
- AI in GTM: What’s Really Working in Practice with CMOs of Seismic, Sprout Social and Deepgram
- Dear SaaStr: Who Should Our First Head of Customer Success Report To?
- 5 Nonobvious Learnings from Atlassian’s Path to The First $10B in ARR With Ex-CRO Cameron Deatsch
- Top SaaStr Posts and Videos of the Week: Databricks’ and Notion’s CROs, Tunguz + Lemkin on AI, S-Tier AI vs. B-Tier Humans
- Attn VPs of Sales: Yes, It’s a Tough Job. But No One is Out to Get You.
- Will Buyers Ultimately Pay More for AI? Vendr’s Data Says … Maybe Not
- Dear SaaStr: How Can I Get Sales and Marketing to Work Better Together?
- The Latest SaaS IPO is a Re-IPO. Expect More of Them
- Going Long: How Procore’s Founder and CEO Tooey Courtemanche Built a Billon-Dollar SaaS Empire Over 23 Years
- Dear SaaStr: What Hours Do SaaS Sales Reps Work?
- AI is Driving a Freemium Renaissance. Run Toward It.
- Carta: 62% of Start-Ups Fail. And 1.3% Become Unicorns.
- Dear SaaStr: How Do You Price a SaaS Product in a New B2B Market?
- Lighter Capital: “We’ve Funded 15+ Companies at SaaStr Annual”
- 5 Interesting Learnings from Shopify at $9B in ARR
- The $10M to $1B Vertical SaaS Playbook: Key Lessons from Procore’s Chief Product Officer Wyatt Jenkins
- Dear SaaStr: What is a Good Refund Policy for a SaaS Product?
- You Could Win $500K – $5M in Funding. Announcing the SaaStr and Mayfield AI Demo Stage and Pitch Competition at SaaStr Annual
- Iconiq: Top Quartile B2B Companies Are Growing 100% at $25m ARR — And Are Planning to Grow 35% Faster in 2025
- How Dialpad Hit $300M ARR by Building Their Own AI Stack: 5 Key Learnings
- Transitioning from Sales-Led to Product-Led Growth and Scaling to $100M ARR With Apollo’s CEO Tim Zheng
- Why VCs Want to Raise Billion Dollar Fund after Billion Dollar Fund
- Dear SaaStr: What Factors Do Investors Consider When Deciding to Exit a Startup?
- 5 Keys Behind Klaviyo’s Path to $1B+ ARR in E-commerce Marketing with CEO Andrew Bialecki
- Top SaaStr Posts, Vids and Pods of The Week: AI at Figma, Ramp & Synthesia; CRO of Owner; YCombinator’s Funding Secrets
- Dear SaaStr: What Causes Co-Founder Breakups?
- The 5 Key Pillars to Machine Learning Success: Real Learnings from 6 Years in the Trenches with Nebius’ VP AI/ML
- The 5 Signs of a Great New VP
- Why Traditional Customer Success is Dead with CCOs of Slack, Mulesoft and OpenAI
- Dear SaaStr: What Types of Due Diligence Do VCs Do For Seed and Series A Rounds?
- 5 Key Learnings from How Top SaaS Companies are Actually Productizing AI with Paragon
- It’s 2025. There Is No “Downturn” Anymore. It’s You.
- From $1M to $3B ARR: Databricks CRO Ron Gabrisko on Scaling a Revenue Rocket Ship
- Dear SaaStr: Does the Bar for “Success” Keep Going Up in Silicon Valley? Will I Ever Be Happy?
- How Top SaaS Companies Drive 2-3x Better Campaign Performance Through Multi-Channel Personalization with Customer.io
- Deel is Growing 70% at $800m in ARR. Does Market Share Matter if Your TAM is Gigantic?
- Dear SaaStr: Is The “Sell Me This Pen” Question Still Relevant?
- Google Cloud + Thread AI: 5 Critical Lessons On Making Enterprise AI Actually Work in Production
- The Next Big Thing in AI Compliance: What ISO 42001 Means for Your SaaS Company with Prescient Security’s COO
- Lessons Learned Rolling out AI Agents to 16,000+ SMB brands with Gorgias’ CTO
- 5 Interesting Learnings from PagerDuty at $480,000,000 in ARR
- Dear SaaStr: Do SaaS Companies Typically Pay Their Sales Reps a Bonus on Renewals? If So, How Much is Typical?
- IBM’s $7B Bet on Vertical AI and What It Means for SaaS Founders
- S-Tier AI is Coming For B-Tier Employees
- The Playbook for Going Upmarket with Stripe’s CBO and Checkr’s COO
- The Truth About Building a Successful Multiproduct Strategy: 5 Key Learnings from Procore’s Journey to $1B+ ARR with its ex-CRO
- One Thing is Clear: AI Makes a Lot of Business Software Look Awfully Expensive Today. Is Deflation Coming?
- Dear SaaStr: What Are The Best Strategies for Raising Capital if Your Goal is To Get Acquired?
- Where AI Really Matters in Vertical SaaS With CEOs of Owner, Alloy Automation, and DoNotPay
- Top SaaStr Posts, Pods & Vids of The Week: Owner’s CRO, HubSpot’s Founder, Tunguz on AI, Synthesia at $2.4 Billion
- Dear SaaStr: What’s the Proper Way to Commission Multi-Year Deals?
- The #1 and #2 Reasons I See Sales Execs Fail Today
- 5 Key Things You Need to Know About AI Data Privacy in 2025 (and Why It Matters) with Skyflow’s CPO
- It Can Take Years to Get Acquired For Millions. So Start Nurturing Those Relationships Now.
- The Future of AI in B2B SaaS: Insights from Synthesia and Theory Ventures. Hosted by Jason Lemkin
- Dear SaaStr: How Do You Handle Customers Upset About an Autorenewal?
- Pitchbook: There Are 300+ SaaS StartUps Waiting to IPO
- How to Build a World-Class Customer Success Machine: Top Lessons from the CRO of Notion and VP of CS at GitHub
- Data-Driven Dominance: The 6-Step Playbook That Zeni Uses to Drive 110% Revenue Growth
- SaaStr’s CRO+CEO Poker Night at Annual is Back!! May 14th!! Apply Now
- 5 Interesting Learnings from Procore at $1.2 Billion in ARR
- Dear SaaStr: How Many Deals Can a Sales Rep Close Per Month?
- When and How to Launch a New Business Line With Justworks’ Head of Product & GTM
- A 10 Point Checklist To Use When You Sell Your Company. Bookmark It.
- Cutting Through the Noise of Gen AI with CEOs of Writer, Orby and Limitless + NEA
- Dear SaaStr: What is the Typical Enterprise SaaS Cancellation Policy for $100k ACV/bigger Deals?
- What’s Really Going in Venture Today: Deals Are Down, But Big AI Dollars Are Up. Per EY.
- The RevOps Playbook: Owner.com CRO’s Secrets to Scaling
- Dear SaaStr: What’s The #1 Thing I Can Implement to Improve Sales performance?
- Top SaaStr Posts and Vids of the Week: Co-Founder of HubSpot, CPOs of Rubrik and GitHub, When Outbound Works, And More!!
- The Keys to Getting to $500M ARR In Just 7 Years with Attentive’s CEO
- Dear SaaStr: As a Co-founder, How Do You Know When It’s Time to Quit?
- The Tough Side of Being Venture Backed: ActOn Sells for $53m After 17 Years … And Raising ~$53m+
- The Creator Lifestyle Looks Overrated. Maybe Stick to Building and Shipping.
- How to Maximize Your Revenue: Strategies to Stop Leaving Money on the Table with Capchase’s VP Revenue
- It’s 2025 And Even Salesforce’s Sales Team is Kind of Phoning It In (At Least Some Of It)
- SaaS Growth in 2025: What Paddle’s $36B ARR Dataset Tells Us
- Just Announced: SaaStr Annual 2025 Headline Speakers: The CEOs and CXOs of Snowflake, HubSpot, Dropbox, ServiceTitan, Canva, Descript, and 100s More!!
- The Enterprise Journey: 8 Keys to Going Upmarket Successfully with Workiva’s CEO Julie Iskow
- Dear SaaStr: What is Your Worst Memory as an Entrepreneur?
- 5 Interesting Learnings from Sailpoint at $820,000,000 in ARR
- What to Expect from a New CRO In The First 90 Days with Kathy Lord, CRO at Zensai
- The Top 10 Mistakes SaaS Startups Make: The 2025 Edition
- The Average Tech Company Pays For 275 SaaS Apps, Flat From Last Year. But It’s Paying 20% More For Them.
- If You Aren’t in the SF Bay Area, Maybe At Least Act As If You Are
- Dear SaaStr: What Do You Do When a Top Employee Slacks Off?
- What’s Really Working in Embedded Finance: Key Learnings from Adyen’s $100B+ Experience
- AI is the Best Thing to Ever Happen to SaaS. Why? It’s Unlocking Even More Budget
- Dear SaaStr: How Do You Know if a Potential Acquirer is Really Interested, Or Just Kicking the Tires?
- The Best of Scaling Vertical SaaS: 3 Deep Dives with The CROs of Slice, Owner and Mangomint
- Top SaaStr Posts, Vids & Pods of Week: HubSpot’s CoFounder, YCombinator’s Secrets, GitHub’s CPO on AI, MangoMint and More!!
- Dear SaaStr: At What Point Should a Startup Hire a Salesperson?
- How to Turn $100K Into $2.7M of Pipeline: Become a SaaStr Sponsor
- WSJ: 23% of Harvard MBAs Have No Job After Graduating. A Record.
- Dear SaaStr: What’s The Top Early Sign a New Manager Won’t Work Out?
- SaaS Is Back, But Different: Insight Partners Raises $12.5 Billion To Invest in More B2B Companies
- What Works Better for Field Marketing: Small, Intimate Events? Or the Big Mega Industry Events?
- Going Multi-Product in the Age of AI with CPOs of Webflow, Rubrik, Zoom, and ProductBoard
- Dear SaaStr: What Are The Biggest Challenges For a Non-Technical Founder?
- 3 Ways to Create and Nurture Great Customers for Long-Term Success with Workato’s SVP Embedded Sales
- When You Raise Venture Capital, A Clock Starts Ticking. At First, Softly. Then Louder and Louder.
- Dear SaaStr: What is The Biggest Difference Between Running a 10 Person Startup and a 100 Person Startup?
- 5 Interesting Learnings from Cloudflare at $1.7 Billion in ARR
- 10 Ways Sales is Different in Vertical SaaS with Mangomint’s VP of Sales
- Lightspeed VC: 100% of Startups See $250k+ Deals Take Longer Than 6 Months to Close
- Your (Belated) SaaS New Year’s Resolution: Add a Layer
- Dear SaaStr: What Are Some Startup Costs That You Didn’t Anticipate?
- Carta: 20% of VC Rounds Last Year Were Down Rounds. It’s Probably Not a Big Deal Anymore.
- AI Should Kill “Contact Me” in 2025. It’s Long Since Time.
- Dear SaaStr: How Bad Does it Look to Be on The Product Team at a Failed Startup?
- LinkedIn: The Greatest B2B Acquisition of All Time?
- The Top SaaStr Posts, Pods and Vids of the Week: HubSpot’s Chairman, Checkr’s CRO, Rippling’s CRO, and a new CRO Confidential!
- Microsoft Pays Its AI Engineers 48% More. What About You?
- 8 Quick Ways to Get More High Quality Leads. Right Now.
- Your Much Bigger Competition Isn’t Always Out to Get You. They Often Just Don’t Really Care.
- Adding AI to SaaS: Inside the AI Product Strategies of Figma, Cloudflare, GitHub and Ramp
- Dear SaaStr: What Are The Biggest Problems You Face as a Startup Founder?
- Crunchbase: 50% of VC Capital Went to SF Bay Last Year, Q4 Roared Back for Venture Capital
- The #1 Worst Hire of All When You Are Just Starting To Scale: The Mediocre VP of Engineering
- Dear SaaStr: What Are Some Successful SaaS Leaders Without Sales Teams?
- 5 Interesting Learnings from Asana at $750,000,000 in ARR
- When Your Founders Turn Down Nine Figures: The Beast Mode 2.0 Framework
- Usage-Based Revenue Models: Successes and Pitfalls from Checkr COO Lindsey Scrase on CRO Confidential
- What’s Better, X/Twitter or LinkedIn? Our Data and Some Learnings
- SaaStr Is #1 on Pavilion’s Revenue Leader Podcast
- The #1 Reason Deals Don’t Close: 53% of The Time is “No Reason”. Do Better Here.
- Dear SaaStr: What Were Your Toughest Times Before Breaking Out?
- It’s Not Just You: Founders Worry More About the Competition as They Scale, Not Less
- Never Hire a “Strategist” Unless That’s Exactly What Your Want
- Dear SaaStr: How Much Do I Pay My First Sales Rep?
- Carta: 38% of Bootstrapped Start-Ups Have Solo Founders. But Only 17% of VC-Backed Ones Do. And 10%-12% of Ones That IPO.
- Top SaaStr Posts, Videos and Pods of the Week: HubSpot’s Founder, Rippling’s and Bill’s CROs, Gong’s $100k Deals
- The Double-Stretch VP Rarely Works Out
- Dear SaaStr: My Salesteam Doesn’t Want to Do Outbound or Visit Customers in Person. How Can I Get Them To Work Harder Here?
- The Real Question for Outcome-Based Pricing Is If It Will Stick
- What Really Works When Hiring VPs, and How M&A Really Works, with HubSpot Co-Founder and Chair Brian Halligan + Jason Lemkin
- Dear SaaStr: Which SaaS Products Offer ONLY Annual Pricing?
- SaaStr Annual 2025 Running at 156% of 2024. SaaS is Back!!
- 2025 And The Rise of the “Mech AE” (Account Executive)
- Dear SaaStr: What Was Your First Meeting Pitching a VC Like?
- 2025 Should Be Better Than 2024 For Almost All Leading Public SaaS Companies
- 78% Of You Are More Bullish About 2025 Than 2024
- Dear SaaStr: Will the Failure of Bench Make VCs Reconsidering Replacing Founders as CEOs?
- Most SaaS Apps Are Just Getting Starting With AI. 2025 Will Be Radically Different.
- The Top 10 SaaStr Videos and Podcasts of the Year: CEOs of Rippling, Klaviyo and Automattic; YCombinator’s Secrets; State of AI Cloud; and More!
- Dear SaaStr: How Do You Evaluate Startups for Seed Investments?
- Yes, You Need to Focus. But in 2025, Step Up or Step Aside.
- Dear SaaStr: What Is It Like to be Pitched by Startups as an Investor?
- The Top SaaStr Posts and Pods of the Week: OpenAI on Pricing, HubSpot’s Chairman on AI, How to Sell to Developers, and More!!
- Dear SaaStr: Why Do Big Companies Buy Small Companies Instead of Competing?
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