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10 Things That Are Different in Vertical SMB Sales with Toast’s CRO
Jonathan Vassel, CRO at Toast helped scale the company from $20M ARR in 2017 to $1.7B+ ARR in Q1 2025 and a stunning $25B market cap. A look back here at the top 10 learnings from his deep dive with Sam Blond on SaaStr CRO Confidential Most SaaS companies sell horizontally to desk workers across…
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The Complete History of HubSpot’s Net Revenue Retention: From 88.6% at IPO to 115% Peak — And Why 102% Today Is Still Strong
A deep dive into one of SaaS’s most dramatic NRR transformations and what it teaches us about scaling retention in the SMB/mid-market When HubSpot filed for their IPO in August 2014, their S-1 revealed a sobering metric that would have made many investors pause: an 88.6% annualized subscription dollar retention rate. For a SaaS company…
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Dear SaaStr: How Do I Monetize a Product Without a Clear Budget Line Associated With It?
Dear SaaStr: How Do I Monetize a Product Without a Clear Budget Line Associated With It? First, bear in mind every organization from the smallest SMB to the largest enterprises has some discretionary budget. When I was a VP at F500 Tech Company, I was the most junior VP, but I still had a $400,000…
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