Dear SaaStr: How You Deal With Long Sales Cycles, E.g. 7-8+ Months? "What's the best way to shorten a long saled cycle from 6 months to 4-5 months? Hire a truly great CRO / VP Sales. They know how to do this. They know how to move deals faster. How to talk to more stakeholders….
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Dear SaaStr: What’s #1 on the path to becoming a great VP of Sales? Each story is different, but there is one clear penultimate step: recruiting and managing a small sales team yourself. From scratch. What 95 times out of 100 is a recipe for failure is jumping straight from successful individual rep to VP…
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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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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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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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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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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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Dear SaaStr: I’ve Gotten to $1m ARR Selling Myself. What Should I Look For in My First Ever Head of Sales? You’re in a good spot—above $1M ARR and still founder-led sales. That’s a strong foundation. Now, as you’re automating and refining your sales process, you’re getting close to the right time to bring in…
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Dear SaaStr: What Are The Top 10 Metrics For SaaS Companies To Track? The key KPIs for SaaS companies revolve around growth, retention, efficiency, and customer success. Here are the most critical ones: ARR (Annual Recurring Revenue): This is your North Star. It’s the total recurring revenue you’re generating annually. Every SaaS company lives and…
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Dear SaaStr: What Do I Look For In My First Marketing Hire? Hiring your first marketing leader is a pivotal moment, and it’s easy to get it wrong if you don’t approach it strategically. The vast, vast majority of “marketers” are just not the right fit to be your first marketing hire and leader. Here’s…
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"Bootstrapping wasn’t a magical choice for Mailchimp. No one would fund them."https://t.co/I0X6sJVY5t — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) May 22, 2023   Dear SaaStr: If you started a new company today how long would you be bootstrapped for before seeking funding? If I were starting today — and in a sense, I’m running this experiment in…
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Dear SaaStr: When Should We Start Pushing For Multi-Year Contracts? For most of us: stop pushing for them in the Age of AI. The market has shifted, and fighting it costs you more than it gains. Here’s the reality: shorter contracts are now the norm across B2B + AI, and it’s rational buyer behavior, not…
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Dear SaaStr: Where should a new head of product focus in their first 30 days? My strong advice is speak with data. And that may mean at first — not speaking too much! 🙂 "When I joined Harvey, I did a listening tour with 60 lawyers and law firms my first few weeks." CPO @harvey Anique…
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Dear SaaStr: Does Freemium Always Work? No. Freemium and PLG models don’t always work. And sometimes, they only work partially. "For Freemium and PLG to work at scale, you probably need millions of folks to use your product. If it's 1000's … then go sell it." pic.twitter.com/2DI6meGWE2 — Jason ✨👾SaaStr 2025 is May 13-15✨ Lemkin…
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Dear SaaStr: How Do We Close Bigger Deals? If you already have a few bigger deals under your belt, but most are smaller … a few higher-level suggestions: #1. Hire a Very Good CRO / VP of Sales that has sold at your “high end” price point. They will be much better at you than…
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Dear SaaStr: When My Startup Raises $10m, Would It Be Appropriate to Take a $170k Salary (no co founders)? Yes, not a problem. You should take a “market correct” salary as soon as it’s economically immaterial to the company. I don’t write $10m checks. I write, typically, $1m-$5m checks, the stage before that. But. As…
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Dear SaaStr: Why Are Pricing Tiers So Effective? I’m no pricing psychologist or true expert, but a few learnings: Buyers like a >few< choices. Not too many, but 1 or 2. It empowers them. In product marketing and sales, always give a buyer that is interested, but dragging her or his feet … choices. One…
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Dear SaaStr: Should I Publish My Pricing? If you aren’t sure — then yes. Transparent pricing has many advantages: It makes the sales process simpler. It allows prospects and leads to do more discovery work on their own. And it places your app in pricing context with other apps. It makes the sales process faster. …
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Dear SaaStr: After closing a few deals myself as a founder, I hired 2 SDRs and closed some more. Should I hire an AE to take over the SDRs and close or a VP of sales? Try to find a VP of Sales now, and try to hire an AE now. You probably will find…
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Dear SaaStr: Why Are VCs So Adamant About Warm Intros? I’ve learned that 90% of warm intros are the biggest waste of time of all, unless they are “double qualified”. Some startups I funded on a cold email: Talkdesk, worth $10B TodayAlgolia, worth $2.25B TodaySalesloft, Vista at $2.3B Pipedrive, acquired for $1.5B Look, worry less…
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Dear SaaStr: How do VCs Really Feel About Founder Salaries? I Was Told That a General Rule of Thumb is 75% of Market The 75% Rule once you are VC Funded for more than a few million dollars is a good one. But if you raise less than that — 75% may well be too…
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Dear SaaStr: How Do I Price My SaaS Product in The Early Days, Before Product-Market Fit? Just start with comps. With comparables. Software is very expensive to build, but for the most part, costs almost nothing to ship. It might cost you $0.10 a month in hosting charges per user for an app that isn’t…
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Dear SaaStr: Should I Cap Commissions of My Top Salespeople? They Make So Much Not until the company is very big — if even then. It’s often the case that top sales reps close 2x to as much as 5x as much as an average rep. With the exact same / equal leads. And you…
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"The #1 mistake founders make when they hire their first VP of Sales? Or even just their first sales rep? They step back from sales. No. You don't get that time back. It's just what you do in sales, changes." pic.twitter.com/wwUzRvrbt0 — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) July 29, 2026 Dear SaaStr: When Should The CEO…
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Dear SaaStr: When Should a Startup Hire its First Sales Person, and What Should Their Profile Look Like? We’ve talked a lot about this on SaaStr, let me summarize my top learnings from 15+ years Try to close at least 10–20 customers yourself first, before you hire a sales rep. You can’t teach them how…
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