Dear SaaStr: What’s It Really Like to Be CEO of a Startup? Let me just throw out a few things I’ve learned that being a CEO of start-up isn’t, or isn’t as you’d expect: It isn’t glamorous until you are At Scale and Hot, at the very minimum. At $10m-$20m+ in revenues, maybe. Maybe not even until pre-IPO….
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Dear SaaStr: What is The Biggest Pain for a CEO? Competition is stressful. Raising funding can be hard. Partnerships can be frustrating. But the hardest part is always recruiting. And it never gets easier, not really. Every CEO I see past $2m in ARR or so, be it Unicorn, IPO’d, or figuring out how to…
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Dear SaaStr: What Are The Top 5 Things I Should Know Before Starting a SaaS Startup? My Top 5: It will take you at least 24 months to really get anywhere. Everyone mentally budgets 10–12 months. It’s never enough. At least, not to get enough paying customers from Code Zero. an AI and vibe coding…
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Dear Saastr: As a CEO, How Do You Know That Your New Employee is an A,B, or C Player? You might not at first. So get help. But you’ll get better at this. As a first-time manager, you really won’t have the experience to know really who is an A, B or C player for…
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Dear SaaStr: A big customer payed for a year but doesn’t use the product. Should I just mark them as churned? No. Don’t necessarily count a big customer out that hasn’t deployed … yet. Instead, what you should try to do is renew them, especially in the enterprise. Go help them actually deploy the software. …
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Dear SaaStr: When Is It Worth Enforcing an Autorenewal Clause if the Customer Doesn’t Want to Pay? Dear SaaStr: When Is It Worth Enforcing an Auto-Renewal Clause if the Customer Doesn’t Want to Pay? Never. Just turn it off. Auto-renewal clauses are absolutely worth having in your contracts. You really don’t want to chase customers…
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Dear SaaStr: What qualities do the great salespeople have? When I'm ready to buy, A great sales rep makes it easier. And better. And gets all my questions answered. A mediocre rep just makes it harder. — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) April 2, 2022 A few qualities of the best sales reps:: 1. They really…
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Dear SaaStr: Is There Any “Con” In Giving Our Sales Tool For Free to Early-Stage Startups? Free can absolutely work. Done right, it’s built some of the biggest companies in B2B + AI: ChatGPT. Claude. Cursor. Slack. Zoom. Canva. Notion. Figma. Almost every AI video generation tool out there. All built massive businesses on the…
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Dear SaaStr: At What ACV Can We Afford a Sales Team? The short answer hasn’t changed much: it’s still tough to afford a human sales team below $299 a month / $3k a year ACV. At least in the U.S. and Western Europe. The math just doesn’t bend enough. But here’s what has changed: AI…
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Dear SaaStr: If We Have Two Overlapping Products is it Better to Have One Sales Team or Two? It’s almost always better to have different sales teams handling different products Why? If for no other reason — Incentive Alignment. Sales reps work on commission, and they are driven almost entirely by what they get the…
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Dear SaaStr: How do I prepare myself to become a successful startup CEO? My list of 6 things that will help: #1. Manage People This is one of the best things you can do, because 50% of the job of a CEO is recruiting a team, leading a team, empowering a team, convincing a team….
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Dear SaaStr: What Are The Biggest Lessons You’ve Learned from Failure as an Entrepreneur? Don’t Fail. I’ve almost failed several times. Really almost every time. But never actually failed. Why not? Never quit. You can’t fail if you don’t quit. Find great co-founders. If you find truly great cofounders, you always have another card to…
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Dear SaaStr: When Is It Too Soon to Target Enterprise Customers in SaaS? It too soon to target enterprise clients when you can’t support their needs 90 days after you close them. It’s sort of OK in the enterprise to promise features and functionality that are sort of there … so long as you deliver…
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Dear SaaStr: How Can You Land Big Customers If You’re a New Startup No One Has Heard Of? Solve one of their top pain points, for real — that no other vendor is solving. And do it in a way that isn’t super risky. If you haven’t sold to the F500 / Global 2000 before,…
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Dear SaaStr: What Should a Bootstrapped Startup Focus on during the Initial Stages of Revenue Growth, Getting More Customers or Making a Few Customers Really Happy? It’s a question I hear all the time. Especially bootstapped startups have so few resources. Should we put them into the few customers we have, or into getting the…
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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 VP of Sales that has sold at your “high end” price point. They will be much better at you than this. At…
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Dear SaaStr: How Can You Ensure a Smooth Transition When A New Team Member Takes Over a Customer Account? Add value in the first interaction. This is so rare. There’s nothing more frustrating than getting a random email, “Hi, Tony is gone from the company. I know nothing about you, but I’m your new rep….
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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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Dear SaaStr: Can A SaaS Startup Really Scale With 2 Co-CEOs? Many will tell you it’s a bad idea, and it probably is — in most cases. I sort of tried this myself, and it didn’t quite work. We had all the classic problems of unclear authority, especially as times got tough. But here’s the…
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Dear SaaStr: What are some no-no’s when it comes to funding a startup — and working with VCs? Here’s my list of top No-No’s: Never assume your existing investors will write you another check. They may, but it’s hard to predict if they will. Just assume any more money has to come from new investors….
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Dear SaaStr: Which Tactics Always Work to Drive Down Churn, and Drive Up Retention? The best tactic I’ve ever seen is a simple combination of 3 things: Measure it, Segment it, and Drive it Down — Irrespective of Where It is Today. Churn is a bummer, and high churn is bad. But I’ve yet to…
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Dear SaaStr: Should an early- stage B2B startup meet every customer face-to-face to receive feedback? If you could — all of them. The more customers you meet in person, the more that buy from you, and the more “more stuff” they buy from you after,. The full data here from Toast, Brex, Slice and more…
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Dear SaaStr: How Long of a Ramp Period Should I Give a New VP of Sales? Look, to be clear, the best ones just hit the ground running. Their first week and really even their first day. Everyone else … looks a little lost when they start 😉 For a Head of Sales at a…
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Dear SaaStr: What are the signs that an enterprise SaaS startup is ready to scale by hiring more sales people? In the early days, it’s simply that you have a few more leads than you can currently handle. For a higher-velocity, in-bound driven B2B product, most sales reps will have trouble processing more than 50…
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Raise prices on existing customers,Doesn’t help if you are growing quickly. Just makes them unhappy. Raise prices on new customers,Forces you to deliver more value. Often makes everyone more happy. — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) April 7, 2022 Dear SaaStr: How Do You Change the Price of Your SaaS Product Without Upsetting Existing Customers? My…
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