Dear SaaStr: Why do customers hate salespeople? Disalignment. A truly great salesperson is a resource. They help you: They educate you on the product. They honestly answer your questions. They address your concerns, seemingly patiently. They help you pilot / test the product first, in a way that drives things forward without too much pressure….
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"You probably don't need as many reps as you think you do" @kylecnorton CRO @owner. "More likely you have a pipeline problem. Spend the money there until your reps' calendars are truly full." cc @samdblond pic.twitter.com/XqfgZOlafj — Jason ✨Be Kind✨ Lemkin  🇮🇱 (@jasonlk) April 17, 2024 The other day I met with a great…
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Two successful SaaS leaders talk about product alignment, freemium models, having an open-source product and other topics in SaaS we all want answers to.

So just a little while back, Lenny Rachitsky had me on his hyper-popular podcast to talk about scaling sales, from the perspective of a founder who hasn’t really done sales. It ended up being super popular, and a fresh take on a lot of topic we talk about a lot on SaaStr. I still regularly…
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I’m not that great at sales myself (not really), but I am a student of it. A few things I’ve observed about human behavior, negotiation, and good and bad sales processes in SaaS: Customers that expect a discount really expect a discount. It’s generally easier to mark up the pricing a bit, then discount —…
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SaaStr’s CRO Confidential podcast host Sam Blond chats with the CRO of Apollo, Leandra Fishman, about Apollo’s success in a competitive market, emphasizing product differentiation, value-based selling, and the importance of customer relationships in driving sales success.

Dear SaaStr: Is It Normal to Feel Like a Pest When Prospecting for Customers For a Startup? Yes. Get better at it, get over it, and hire folks who know how to do it. Boy sales is hard. It’s being told No a lot. It’s having literal, or virtual, doors shut on your face. Sales…
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Things mediocre sales reps say: 🤷"So it turns out they don't have budget after all" ❓"I had a great call with a customer! Not sure about next steps, though." 💸"Can I discount even more?" 🤣 "Where do I find the collateral again?" — Jason ✨Be Kind✨ Lemkin  🇮🇱 (@jasonlk) February 14, 2024 Sales is…
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So a few stories from the past few weeks reminded me of a meta-challenge in managing a sales team in the founder-led sales: so many sales execs need to be micromanaged, at least up to a point. It’s not just me. Sam Blond, CRO of Brex made a similar point at our SaaStr Miami Super…
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The path to Cheif Revenue Officer (CRO) is different for many people. Tracy Young, CEO and co-founder at TigerEye, sits down with three CROs to talk about how they navigated the journey to revenue leader. Jane Kim, former CRO of CircleCl, Laurabeth Harvey, President of Field Operations at Lattice, and Erica Anderson, Notion’s CRO, all share the key decisions or events that shaped their careers.

At SaaStr Miami, former Founder’s Fund Partner and CRO of Brex Sam Blond — host of the SaaStr CRO Confidential Podcast — sat down with SaaStr CEO and founder Jason Lemkin for a fireside chat about finding success as a SaaS company in 2024. They discuss Sam’s learnings at Founders Fund, what the 2024 playbook looks like, hiring and motivating sales teams, and a handful of audience questions.

Dear SaaStr: Should I Hire a Sales Rep First, Or a Sales Manager First? The ideal flow is: You (founder-CEO) close the first batch of customers, say the first 10 or 20. If you don’t, you’ll never really know how it’s done. Or be able to help anyone else, really. Then, once you know how to…
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Dear SaaStr: How Do I Increase Pricing Again Without Angering Customers? One simple thought: earn it. First, plan to increase pricing in general once a year, each year for new customers. But earn it. And generally for new customers, not existing customers. How much? Well, that will depend on how much additional value you’ve added…
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So you’re hiring your first few sales reps in the early days? Before you have a great VP of Sales? It’s an interesting time. Leads are precious, everyone is a team. So you need a very certain type of sales rep. Let me give you a checklist of a few signs they won’t work out:…
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In my first start-up, I was mostly hunting whales — seven figure and eight figure deals. I had no experience doing any of this. For our First Big Customer, we’d been negotiating a $6m/year contract for quite some time (they always take time). We finally had the “all hands” meeting with all the C-level and…
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