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The Silent Churn: Why Your Best Customers Often Leave Without a Word. We Just Did.
Jul 27, 2025
A $60,000 lesson in customer success. Eight years. That's how long we've been paying a vendor $60,000 annually. Eight years of being what most B2B companies would call a "good customer" — we paid on time, didn't complain much, and frankly, we were probably easy to...
The $400B HR Tech Boom: How Old School ADP & Paychex Are Thriving Alongside Rippling, Deel & Gusto
Jul 27, 2025
The Bottom Line Up Front: The HR tech market is experiencing an unprecedented boom with room for multiple $100B+ winners. While ADP trades at 6.5x revenue with a $132B market cap and Paychex commands an 11x multiple at $56B, the newer players are building massive...
Dear SaaStr: What Will Need to Change The Most As We Approach $100m ARR?
Jul 27, 2025
Dear SaaStr: What Will Need to Change The Most As We Approach $100m ARR? At $100M ARR, everything changes. It’s a whole new game. https://www.youtube.com/watch?v=IVfT9hY6J3Q The challenges you face at $50M ARR will feel like a warm-up compared to what’s ahead. Here’s...
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The Silent Churn: Why Your Best Customers Often Leave Without a Word. We Just Did.
By Jason Lemkin | July 27, 2025
A $60,000 lesson in customer success. Eight years. That’s how long we’ve been paying a vendor $60,000 annually. Eight years of being what most B2B companies would call a “good customer” — we paid on time, didn’t complain much, and frankly, we were probably easy to forget about. But … we’ve been using their product…
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Blog Posts
The $400B HR Tech Boom: How Old School ADP & Paychex Are Thriving Alongside Rippling, Deel & Gusto
By Jason Lemkin | July 27, 2025
The Bottom Line Up Front: The HR tech market is experiencing an unprecedented boom with room for multiple $100B+ winners. While ADP trades at 6.5x revenue with a $132B market cap and Paychex commands an 11x multiple at $56B, the newer players are building massive businesses too: Rippling at $16.5B (29x revenue), Deel at $12.6B…
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Blog Posts, Q&A
Dear SaaStr: What Will Need to Change The Most As We Approach $100m ARR?
By Jason Lemkin | July 27, 2025
Dear SaaStr: What Will Need to Change The Most As We Approach $100m ARR? At $100M ARR, everything changes. It’s a whole new game. The challenges you face at $50M ARR will feel like a warm-up compared to what’s ahead. Here’s what you can expect as you scale to $100M: Your TAM Will Be TestedBy…
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