10 Ways to Build a Moat in SaaS. But AI is Also Making Them Weaker.
The real moat in SaaS is brand Almost every market leader has a really, really good competitor or 2 or even 3 That would honestly do the job just as well — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) February 5, 2025 A while back we did an extra “Day 0” AMA...
Eventually … Almost Everyone Has a Sales Team
Eventually … everyone goes a bit enterprise Eventually … everyone adds a sales team https://t.co/6h3LesrvRo — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) October 16, 2025 The lure of freemium (like The Force) is strong. No headaches. Customers try and...
5 Ways AI Has Already Changed SaaS Sales Forever with Perplexity’s CBO Dmitry Shevelenko and SaaStr CRO Confidential Host Sam Blond
Perplexity’s CBO Dmitry Shevelenko and host of the SaaStr CRO Confidential series (and former CRO at Brex), Sam Blond at SaaStr Annual share how AI has already fundamentally rewired how SaaS sales works.
30+ Tough Learnings from Losing a Top Customer
On both SaaStr University and Twitter, we had 30+ founders, CEOs and execs share their top, tough learnings from losing one of their top customers. There are some great teachable moments here, and also some deja-vu if you’ve been through it! “I should...
That Super-Successful VP of Sales. Great? Or Just Lucky?
I get sent this resume to review all the time. Director+ of Sales at Slack / Zoom / Mongo / Datadog / Qualtrics Your Brand Name SaaS Company. Took Hot Start-Up from $0 to $50m as VPS from Day 0. Was there “early” through IPO and did amazing things. That all sounds...
The 1 Simple Test to Know if You’ve Actually Hired a Real VP of Product or Customer Success … Or Not
I remember the first time I had a “head of product” in SaaS. I’d known him for many years, and knew he was great … but didn’t really know what help he could give us. I just knew we needed help around $2m-$3m so I asked him to help. I...
Dear SaaStr: How Do I Convince My Customers with Monthly plans to Upgrade to Annual Plans?
Dear SaaStr: How Do I Convince My Customers with Monthly plans to Upgrade to Annual Plans? My advice: Don’t. It’s too many calories expended for not enough benefit. Let me explain what I mean … Large customers only pay via invoices, especially for any deal of any...
Fake Multi-Product vs. Real Multi-Product
Go multi-product too early, it’s a huge distraction Go multi-product too late, growth stalls Getting it right is a key part of the CEO’s job after $10m-$20m ARR — Jason ✨👾SaaStr 2025 is May 13-15✨ Lemkin (@jasonlk) January 2, 2024 So one thing that’s...
CRO Confidential: How Windsurf Built A Billion-Dollar AI Company and a Winning Sales Machine with VP of Worldwide Sales, Graham Moreno
Join us on this episode of CRO Confidential as host Sam Blond dives into the remarkable journey of Codium’s VP of Worldwide Sales, Graham Moreno. Discover how Graham led Codium from a 30-employee startup to a unicorn with 150 employees in just one year.
Dear SaaStr: What’s The Hardest Part About SaaS Companies, At Each Stage?
Dear SaaStr: What’s the Harder Part About SaaS Companies, At Each Stage? The hardest part changes every 12–24 months, and the whole company changes every 30-36 months or so. But a few thoughts on “the hardest part” for the first few stages: From $1-$100k in...
Dear SaaStr: Should SaaS Startups Really Have CROs or COOs? Is That Too Many Management Layers?
Dear SaaStr: Should SaaS Startups Really Have CROs or COOs? Is That Too Many Management Layers? A few years ago, I would have said No. There’s no way a SaaS startup needs a “CRO” or “COO” or other C-level Officers Without a Clear, Single Functional Area to Own Until...
Dear SaaStr: How Many Sales Reps Do I Need?
Dear SaaStr: How Many Sales Reps Do I Need? More than you probably would think. You can back into how many sales reps you’ll need in SaaS: First, figure out how much sales-driven revenue you need to close in the next twelve months. Because that’s more than now....
Dear SaaStr: What is a Good Refund Policy for a SaaS Product?
Dear SaaStr: What is a Good Refund Policy for a SaaS Product? SaaS startups, especially those that sign customers to annual customers, will have customers that want to cancel those un-cancelable contracts and get a refund. Even customers that pay monthly on credit...
Dear SaaStr: What Causes Co-Founder Breakups?
Dear SaaStr: What Causes Co-Founder Breakups? Yes. I’ve had one, and watched several. It’s really tough to go through. The root cause for mine, and most of the ones I’ve observed, is disalignment on goals and outcomes: Do you want to IPO, but your cofounder would be...
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