All Agencies and Contractors Have a Half Life. Move On Once You Hit It.
The best marketer I've ever worked with said to me early that you have to fire all your agencies after 6 months Why? They give you their best upfront, and then turn the gig into an annuity staffed with the mediocre I thought it was a bit aggressive But he was...
4 Unexpected Learnings from Klaviyo: How They Built a $1B+ ARR Marketing Platform That E-commerce Customers Love
Klaviyo: The $1B+ ARR Powerhouse Built on Top of Shopify Klaviyo has quietly built one of the most impressive SaaS platforms for e-commerce with ~$1B ARR growing at 35% annually, 112% NRR, and impressive 14% free cash flow margins. What makes Klaviyo unique...
Dear SaaStr: How Can I Become a Better VP of Sales?
Dear SaaStr: How Can I Become a Better VP of Sales? Being a great VP of Sales is about balancing leadership, strategy, and execution. You’re not just managing a team—you’re driving revenue, building scalable processes, and ensuring alignment across the company. Here’s...
5 Interesting Learnings From Workday at $9 Billion in ARR
So who will benefit the most from AI in B2B? The hot new start-ups, rocketing to $100m ARR in record time? Or … the established leaders, who can add AI onto their apps and not just expose vastly more functionality, but leverage all that existing customer data,...
Kruze: The Average Startup CEO Salary Is Up to $161,000
Kruze Consulting helps a ton of B2B start-ups manage their books and finance so their latest data on comp for start-ups is super helpful. Across 400+ startups, mostly B2B, they break down comp. For seed stage: CEO: $147,000 CTO: $134,000 COO / Operations: $135,000...
Dear SaaStr: How Do I Handle a CEO I Can’t Trust?
Dear SaaStr: How can I handle a distrustful, lying, and micro-managing CEO that I am reporting to at a startup I co-founded? Quit. If you are that angry — It’s Time. But — quit quietly with grace. Leave if not happy, pretend happy. Leave...
The Problems with “Small But Mighty” AI Start-Ups
So it’s become a thing with many founders and VCs to think how far you can go in AI today. Many of the early break out leaders in AI for B2B and otherwise have been “small but mighty teams”.  And it’s not a completely new vibe.  Instagram had just...
Building and Scaling an AI Company in 2025: What Top VCs Really Want to See with Zetta, Glasswing and B Capital
A deep dive with three leading AI investors who collectively manage billions in venture capital and have backed some of the most innovative companies in artificial intelligence. The Expert Panel Karen Paige, General Partner at B Capital Karen brings deep operational...
Dear SaaStr: When Should I Hire Our First Sales Person, and Who Should I Hire?
Dear SaaStr: When Should I Hire Our First Sales Person, and Who Should I Hire? "The one cheat code to making your first sales hires. The one cheat code to making sure they actually work out." with @lennysan pic.twitter.com/eULOECEPZw — Jason ✨👾SaaStr...
The Top 10 Learnings from Launching SaaStr’s Own AI: What Every B2B Founder Needs to Know
Our AI just: – helped walk a prospect through the various sponsor options at SaaStr Annual 2025– explained the benefits in perfect detail– and then routed them to a meeting with the partner team Honestly better than any human And at 6:41 pm PST The...
Top SaaStr Posts and Pods of the Week: Wiz and Rippling’s CROs; Google Cloud’s VP of Marketing; And Great Dashboards
Top Posts: #1. The #1 Thing That Makes Enterprise Customers See Value: A Great Dashboard #2. Thoma Bravo: Software Spend Will Grow 19% a Year Through 2028. AI is The Accelerant. #3. Yes, SaaS is Back. But Every CFO I Know Is Still Doing Vendor Reviews. And Still...
4 Unexpected Learnings from Databricks’ Sales Growth Machine From Its VP of Sales
A little ways back Databricks’ VP of Sales Heather Akuiyibo joined SaaStr to share unexpected things that work well at Databricks’ GTM organization … as well as some things that haven’t worked as well. 4 Unexpected Learnings from Databricks’ Sales Growth...
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...
5 Growth Channels That Drove Rupa Health to $100M+ in Value: Head of Growth’s Deep Dive — With Real Numbers
Kobe Conrad, Head of Growth at Rupa Health and Onleet, took the stage at SaaStr Annual to break down the five growth channels that transformed Rupa Health from a $20M seed-stage startup into a platform with hundreds of millions in equity and a 4,000% increase in user...
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