My cut of the episode where Dev Ittycheria, one week back as CEO of MongoDB, told me I was wrong about the biggest story of the week. Thursday’s recap covered all four of us. This is my side of it: ten decisions I’d make sooner after an hour with Harry, Rory, and Dev. #1. A…
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Dear SaaStr: What Are A Few Top Tips to Hiring The Right First VP of Sales? Hiring a great first VP of Sales is one of the most critical decisions you’ll make as a founder. Get it right, and they’ll scale your revenue and team. Get it wrong, and you’ll lose a year. Or more….
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Sherif Mansour has been at Atlassian for 17 years. He runs AI across the product portfolio and owns the product management craft, which means 450 PMs. Atlassian has more than 20 apps. Six were built in the gen AI era and the rest are years old. More than 5 million users now use those apps…
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Remote is a seven-year-old global payroll and employment platform based in Amsterdam. It leaned in early to making payroll (and more) for distributed and global teams work, and is one of the most trusted vendors in the space. Its payroll business has passed $300 million in ARR, growing more than 300% year over year, and…
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Dear SaaStr: When a VP Sales is Struggling, What Do They Start to Do That … They Shouldn’t? Struggling in sales is tough, and you need to give your leadership some time and room to claw back to growth. But here are some signs … they won’t get there: "The #1 sign a CRO isn't…
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An IPO should be Plan A. It’s the best outcome for almost everyone on the cap table. But founders, employees and even a lot of VCs treat the IPO date as the liquidity date. For most of the cap table … most of the money comes years later. Start the clock at the first check…
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When a new CRO / VP Sales shows up to the first board meeting and doesn't know: – The top accounts cold– The top deals in flight cold– Their team and leaders cold– The top deals at risk cold There's like 0% chance it will work out — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) September 28, 2026…
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Dear SaaStr: Should I Use an AI SDR Before I Have a Working Human SDR motion? No. This is the single biggest mistake I see across all company stages, from $1M ARR startups to multi-billion-dollar public companies, and it will sink your AI SDR deployment. The Core Problem If outbound doesn’t work with humans, buying…
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With Harry Stebbings, Jason Lemkin, Rory O’Driscoll, and special guest Dev Ittycheria, back in the CEO seat at MongoDB Dev Ittycheria joined us one week into his second run as CEO of MongoDB. CJ Desai stepped down on September 28, effective immediately, and the board named Dev interim President and CEO. Desai left to run…
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Cloudflare latest quarter reported of $696.1 million, up 36%, which annualizes to $2.8 billion. Three months earlier, it had cut more than 1,100 roles, about 20% of the company, and the stock dropped 23%. In Q2 growth accelerated, and the stock jumped 17% after hours. Four days later Cloudflare raised $2.5 billion at a 0%…
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A mistake many founders make is hiring a CRO / VP of Sales who has many strengths — but is not great at selling themselves per se. In fact, I’d say the majority of B2B CEOs make this mistake when they hire a CRO at they truly begin scaling. That seasoned CRO with the great…
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Dear SaaStr: What Should I Look For In My Very First Sales Rep? The first thing to understand is that hiring your first sales rep is one of the most critical decisions you’ll make. It’s not just about finding someone who can sell—it’s about finding someone who can sell *your product* in the stage your…
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At SaaStr AI we are aggressive users of AI outbound tools: Monaco runs cold outbound. It booked a meeting for us with the right buyer at Anthropic on Day 1. That says it all. Artisan runs warm outbound. It has for over a year and booked millions of closed won for us. It’s where we…
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"The #1 thing that undermines confidence in a CRO: Unexpected Bad News. A CRO should have real visibility into the new few months. They may come in a bit above or below plan. But there shouldn't be massive variances. If so, the plan was Hope-ium." pic.twitter.com/ASbOGcOQs1 — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) September 27, 2026 We’ve…
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Dear SaaStr: My Co-Founder is Threatening to Quit Unless I Give Him More Equity; what should I do? Generally, this is the last, best chance to fix things. Founder equity splits are a tough thing. What seems fair on Day 0 may seem less fair on Day 720. The one that seemed the weaker of…
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