OK Summer is over. That means it’s time to step it up even harder: – Have you been dragging your feet on letting that VP go … that never hit plan?– Are releases … not really going out any faster?– Is the competition pulling even … or even ahead …...
Marc Benioff just provided the ultimate proof point for AI SDRs during his appearance on 20VC+SaaStr: Salesforce has used AI agents to being to tackle 100 million uncontacted leads accumulated over 26 years. 100,000,000. “We just have not had the people,”...
Dear SaaStr: I run a 30M arr software company — operating as both CEO and CRO. I feel like I failing at both – what is a better option? At $30M ARR, you’re at a stage where the demands of both the CEO and CRO roles are too significant for one person to handle...
Some of our most compelling B2B and SaaS founders built their companies from deep domain expertise. Others stumbled into their markets … almost by accident. In the middle, some sort of knew their space, but the journey was an entirely new one. Which is better...
A deep dive from the founder/CEO of FlatFile, building AI agents for enterprise data preparation in highly sensitive environments. And come meet Flatfile at 2026 SaaStr Annual + AI Summit, they’ll be back! May 12-14 in SF Bay!! I’m David Boskovic, the...
Dear SaaStr: What Should Quota Be for a Commercial Sales Rep? Our Deal Size is $20k-$50k For commercial AEs, quotas typically range from $600K to $800K annually, depending on your ACV and sales cycle. At least, once you have a repeatable process. Before that, you...
Will AI take away jobs in tech? Some of course. Even more often, already, it’s leading to headcount being rebooted and used in new ways. Salesforce for example has already repurposed headcount from 1000s of support agents into sales. Same headcount, but different...
When HubSpot rang the NYSE bell on October 9, 2014, at $25 per share, most observers saw another marketing automation company going public. What they missed was witnessing the birth of one of SaaS’s most consistent wealth-creation machines. The scorecard after...
Dear SaaStr: As a startup founder, what’s the shadiest thing a VC asked you to do (to get their funding)? I don’t think anything is truly shady in venture. Deals are generally made at arm’s length, and founders don’t have to sell any shares if they don’t...
We had a real treat this week — Marc Benioff joined Harry, Rory, and Jason on 20VC+SaaStr this week to deliver one of the most grounded and passionate takes on AI we’ve heard from any enterprise leader. In a market fueled by AGI promises and $10 billion...
