Dear SaaStr: Why Do Many Startup CEOs Quit After Their Companies Are Acquired?
Dear SaaStr: Why Do Many Startup CEOs Quit After Their Companies Are Acquired? Five reasons: First, it’s very difficult for most founder-CEOs to work for someone else. They generally don’t mind working with others. They don’t even need to be “the boss”. But being told...
The 3 New Pricing Models in B2B. Pick One, Because The Old One (Just Seats) Really is Dying
Henry Schuck, CEO of ZoomInfo, just posted his read on where B2B pricing is going. His summary, after talking to the world’s most expensive consultants and hundreds of his own customers: nobody knows. Not the experts, not the customers, and the answer keeps...
The Best CROs and VPs of Sales Make Their B Team Shine
Consistency is one of the biggest challenges with enterprise sales. This hasn’t changed at all in the Age of AI. In fact, it’s almost worst, because the best in B2B+AI are scaling faster than ever. Replit is hiring 250+ sales reps this year, up from just...
Dear SaaStr: How Does a Sales Rep Truly Add Value?
Dear SaaStr: Do salespeople add to the value received by customers? They do in the enterprise. At least the good ones do. That’s what a lot of founders miss if they haven’t worked with great mid-market and enterprise sales execs before. Let’s break sales down into 2...
BigCommerce vs. Shopify: When Second Place Is a Very Tough Place to Be
Six years ago, BigCommerce was the credible number two to Shopify in ecommerce software. Not a niche player. The only standalone, pure-play public alternative to Shopify that a public market investor could buy. It was more B2B but worryingly, wasn’t growing...
The Top 5 Reasons I See CROs Flame Out
I saw about 10 CROs leave or get fired the past 12 months across the startups I work with or have invested in at SaaStr Fund. That’s a lot. That’s actually a ton. It may be a record. I suspect it is. AI is the root cause of some of it. As many startups...
Dear SaaStr: How Long is a Venture Round Supposed to Last?
Dear SaaStr: How Long is a Venture Round Supposed to Last? I think like many venture axioms, founders get often get bad advice here out of good solid rules. The classic rule was “18-24 months”. In boom times, it’s still true … it’s just...
Stripe Buys OpenRouter for $7B, Anthropic Turns Its First Profit, and Silver Lake Circles Workday at $43B: 20VC x SaaStr
Plus the math that has to be true for AI to reach $600B in revenue: $100K of tokens per engineer, and 30% fewer engineers. A heavy week on 20VC x SaaStr with Harry Stebbings, Rory O’Driscoll and Jason Lemkin: SpaceX closed its $60B all-stock takeover of Cursor...
Dear SaaStr: Growth Has Slowed and My VP of Sales is Pushing Me To Hire More Reps. Is That The Right Way to Go?
Dear SaaStr: Growth Has Slowed and My VP of Sales is Pushing Me To Hire More Reps. Is That The Right Way to Go? No. Not 9+ times out of 10. Probably 9.8 times out of 10. It’s a desperation move. In fact, the #1 sign your CRO / VP of Sales is really struggling is...
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.
Amjad Masad, founder and CEO of Replit, posted the other day: “I thought I hated sales culture. By the end of this year, more than half my company will be salespeople.” He goes on: for most of the last decade he was a typical tech guy. Build a good...
A Simple 4 Part Test to Know If You’ve Hired the Right VP
Did you hire a good enough VP? 4 part test: – who great did they hire in the first 60 days?– did their #1 key metric improve?– did they take part of the job off your plate?– does the team believe? If they don't pass the 4 part test, they...
ServiceTitan Just Shut Off Podium’s Integration for ~1,000 Shared Customers. Why? Agents Turned a 9-Year Partner Into a Direct Competitor.
When a 9 year partnership … breaks down in the Agent Era. Podium co-founder and CEO Eric Rea posted last week that ServiceTitan gave roughly 1,000 shared customers about 30 days’ notice that the Podium integration was being switched off, in the middle of peak...
Dear SaaStr: How Do You Build a Real Exit Strategy?
Dear SaaStr: How Do You Build a Real Exit Strategy? First, bear in mind acquisitions are relatively rare. The vast majority of startups will never get one strong acquisition offer. Still, it’s not random. I’ve been through it twice as a founder and about...
Vertical B2B Leader Owner Acclerated After $100M ARR With Agents. The Key Insight: Every Time a Customer Logs In, Owner Has Failed.
Everyone agrees you have to build with AI now. That argument is over. The unsettled questions are what a product built on agents is supposed to measure, and what stops a foundation model from doing to you next quarter what you just did to your own category. Adam Guild...
Founder SaaStr
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