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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Dear SaaStr: What’s a Good Benchmark for B2B Sales Cycles? To overgeneralize, but to give you a pretty rough sense: Sales cycles are very much impacted by the intent of the prospect. Intent varies from High Probability / Intent Opportunities (“I Need to Buy Now” — this exploded during the pandemic) to Very Low Intent…
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Dear SaaStr: How Do I Know if My Competitor is Cold Calling My Customers? Just assume your competitor is cold calling all your existing customers. They should be. Be most worried if they are doing it well. They should be calling your customers. Yes, oftentimes the yield here can be low if your customers are very…
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Dear SaaStr: What are the benefits and drawbacks of having co-CEOs? Like many things, my thinking on this has evolved over time. I used to think having co-CEOs was almost always plainly a bad idea. And clearly, it’s still quite rare. But now I think maybe it’s only a bad idea when done for the…
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Dear SaaStr: What is considered a fair or happy medium secondary amount for the founders to take off the table at a Series B VC funding round? Secondary sales done right truly align founders and the company and incent them to go long. See Brian Halligan’s (co-founder and Chairman of HubSpot) great learning and example…
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Dear SaaStr: Should You Ask a Prospect What Competitors They Are Looking At? Yes. And in 2026, more than ever. You’ll find 90% of the time you’ll want to not just tell a prospect who you are competing with, but do so aggressively. And box the competition out at the start. “Great to learn about…
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Dear SaaStr: If I White-label my B2B product, will it hurt me on branding my own company? Just do it. If it’s easy to do. Lots of folks agonize over white-labelling. The brand benefits will go to my partner, not me. I’ll be valued less. Etc. etc. But bear in mind a few things: All…
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Dear SaaStr: How Long Should You Give a New Sales Rep? The tough truth is from 1.0–1.5 sales cycles. And you’ll often, though not always, know sooner. Sales is tough. It’s a lot of Nos to get to a Yes. And while sales is pretty similar in SaaS at a given price point / ACV,…
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Dear SaaStr: I’m Pretty Hands Off on the Sales Team. What Will I Learn Getting More Involved in Sales? The most important thing that you will learn is how businesses truly scale on the revenue side. You may think you know this intuitively, but you don’t: You may think sales organizations magically create revenue. They don’t. They…
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Dear SaaStr: I’ve Got 4 Sales Reps. Should My VP of Sales Have Their Own Quota? Maybe for a sales cycle or so. But not much beyond that. If you only have 4 AEs, then it’s reasonable for your Head of Sales to carry a small quota … at least temporarily. At this stage, they’re…
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Dear SaaStr: Can free pilots and trials periods count towards gross revenue then deducted as a marketing expense? No. First, if you really want to do this — i.e., net a pilot against marketing expense — then you do have to still charge for it. Even if you provide the customer other services. Second, it’s misleading. The…
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Dear SaaStr: Why Do Enterprise Customers Insist on Pilots? I know your sales team probably hates pilots, because in a sense, it means they have to sell the deal twice. Once for the pilot, and again to convert the pilot for a longer deal. Having an “opt out” clause after a pilot ends helps, but…
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Dear SaaStr: What Do You Have to Get Right in a Start-Up? So many folks I meet want to start a start-up. They have an idea they are passionate about. They’ve worked under a great CEO, and they’re ready — they think — to do it on their own this time. What does it take?…
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Dear SaaStr: What’s the #1 Way I Can Accelerate My Career Growth? My uber-learnings: Find the best boss you can; and Take on every initiative, project, task, and endeavor you possibly can from her. And work for them for a while. Long enough to get promoted once, ideally twice. Ideally, 3-4 years. The best career…
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"To really invest in your team, product, etc. you need at least $1 on the balance sheet for each $2 in ARR. At $20m ARR? You need $10m in the bank to make the hires, burn the tokens, etc. to really get to the next level. Below that … you hesitate." pic.twitter.com/Vdgzq0uKxC — Jason ✨👾SaaStr.Ai✨…
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Dear SaaStr: What’s the #1 Reason You See Sales Reps Fail These Days? The #1 reason I see sales execs struggling today in new roles: they are convinced their playbook is better. And refuse to run the one that is already working. They are convinced they know better. That the founders are wrong, or whomever…
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