Dear SaaStr: What’s the #1 Reason You See Sales Reps Fail These Days?
Dear SaaStr: What’s the #1 Reason You See Sales Reps Fail These Days? The #1 reason I see sales execs struggling today in new roles: they are convinced their playbook is better. And refuse to run the one that is already working. They are convinced they know...
We’ve Been Running Salesforce Headless for 6 Months on Our Own “Claudeforce.” We’re Never Going Back
For the past six-plus months, almost no one at SaaStr has logged into Salesforce. The data is all still there. We still pay for it. We still depend on it. We just stopped using the UI as the primary way to get at any of it. Some context on why we did this. SaaStr runs...
10 Things That Tell a VC You May Not Be Ready for “Prime Time”
Being an amateur is OK, even endearing — if it’s authentic. And up to a point. But here are some things that founders do that perhaps suggest you aren’t yet ready to raise venture capital. The good news is, it’s really easy to course-correct and...
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?
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? This is pretty common and most founders make the same mistake. Move on from the rep now. There is almost no chance he is adding value...
Owner.com Did an AI Rebuild to Accelerate Past $100M ARR. The 7 Top Lessons, and What It Takes to Copy Them
Their own customer research said restaurant owners feared AI. It was three months old and completely wrong Adam Guild CEO of Owner.com gave one of the more useful operator talks at SaaStr AI 2026 this year: three years of rebuilding Owner.com around AI, from a website...
What Differentiates The Best Founders? They Really, Really Know Their Stuff
Dear SaaStr: What can entrepreneurs do to stand out to prospective investors during a pitch? The best founders really know their sh*t. The best founders just know everything cold about their business: They know the competition cold. They don’t mock the competition,...
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
Kroll published its Summer 2026 Global Software Sector Update, covering software M&A and public comps through June 30, 2026. It’s 20 pages of deal data with a lot of detail on what the market currently pays for B2B software. The headline numbers read like a...
You’ll Lose Customers. It Hurts. But Don’t Let Them Become Angry Ex-Customers.
"If a customer wants to go, let them. In fact, help them. First, it really doesn't matter when they go, if they go. They drop off your ARR eventually. Second, treat them right, they may well come back." pic.twitter.com/QrDVkLyd19 — Jason...
Dear SaaStr: What’s The Best Way to Fire Your Co-Founder … Who Was Once a Friend?
Dear SaaStr: What’s The Best Way to Fire Your Co-Founder Who Was Once a Friend? It’s pretty common that a co-founder doesn’t work out, unfortunately. I’ve been a part of all versions of this: I’ve had a great co-founder that went the...
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
Episode #013 of The Agents is here! Same setup as always: three humans, 20+ agents in production, an 8-figure B2B + AI business. This week was about what happens when agents take over the system of record. ServiceTitan just cut off Podium over exactly this question....
50% of the Work Created in Linear Is Now Created by Agents. A Year Ago It Was 3%.
Linear published its tender offer news this week: $99 million of secondary at a $2.5 billion valuation, up from $1.25 billion at the Series C last year. Accel and 01A participated, with Salesforce Ventures and S32 coming in new. No primary capital raised....
If the CRO / VP of Sales Doesn’t Believe, It’s All Over. You Both Just Need to Move On
If the VP of Sales Doesn't Believe, It's All Over for them, at your company. You'll have to find a new one. – Back them– Help them– Get them budget– Join the calls– Go visit customers together– Get on the Zooms–...
Dear SaaStr: Should I Do a Dinner or a Booth at a Big Industry Event? Or Just Buy Tickets?
Dear SaaStr: Should I Do a Dinner or a Booth at a Big Industry Event? Or Just Buy Tickets? So the next event cycle is coming up. Dreamforce. SaaStr will be there in force, both with a booth and a dinner. Inbound, AWS Reinvent, and more. You will hear a lot of advice...
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
Harry Stebbings, Rory O’Driscoll and I went through Nvidia’s ecosystem spending spree, OpenAI’s move from number one to number two, and what happens to CFO budgets when your best people are addicted to tokens. #1. Nvidia paid $6B for...
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