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Blog Posts, Early, Q&A
Dear SaaStr: What Are the Top Mistakes You See New Founders Make?
Dear SaaStr: What Are the Top Mistakes You See New Founders Make? My short list: Not picking a great co-founder. There’s almost no point in picking one that isn’t truly,…
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Blog Posts, Fundraising, Q&A
Dear SaaStr: Why Is a “Downround” So Bad?
Dear SaaStr: Why Is a “Downround” So Bad? Down-rounds shouldn’t be such a big deal — if the private stock markets worked more like the public ones. Public stock prices go up…
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Blog Posts, Early, Q&A, SaaS Product Pricing, Sales
Dear SaaStr: Should We Charge for Pilots and How Much?
Dear SaaStr: Should We Charge for Pilots and How Much? Charge for any true pilot. If you don’t charge, it’s not a pilot. It’s an extended demo. Now, that’s better…
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Dear SaaStr: When Do Free Trials Work Well?
Q: Is free trialing still an effective way to get customers in your B2B SaaS these days? Free Trials are Great. And really, it would be great if every app…
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Growth, Q&A, Sales, Sales
Dear SaaStr: Are Clawbacks in Sales Applied if the Customer Has Paid in Full?
Dear SaaSt: Do sales commission clawbacks typically apply after a customer’s payment has cleared (e.g. if they ask for and are granted a refund) or only up until payment is…
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Dear SaaStr: Is It OK to Fly First Class to Close A Big 7 Figure Deal?
Dear SaaStr:As a founder of a series A startup, was it unreasonable for me to use the company’s money for first class tickets? A European company was interested in doing…
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Blog Posts, Early, Other, Product, Q&A
Dear SaaStr: How Do You Know If Your Startup Idea Already Exists?
Dear SaaStr: How Do You Know If Your Startup Idea Already Exists? Well, of course it already exists. You really think you’re the only person on the entire planet that…
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Blog Posts, Early, Fundraising, Leadership, Q&A
Dear SaaStr: How Long is a Venture Round Supposed to Last?
Dear SaaStr: How Long is a Venture Round Supposed to Last? I think like many venture axioms, founders get often get bad advice here out of good solid rules. Until…
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Blog Posts, Fundraising, Q&A
Dear SaaStr: How Does an Investor Protect Themselves When Investing in a Startup?
Dear SaaStr: How Does an Investor Protect Themselves When Investing in a Startup? It’s actually pretty hard. Investing in startups actually requires a lot of trust by VCs and investors….
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Blog Posts, Q&A
Dear SaaStr: I am Leaving a Startup I Co-Founded on Good Terms. Should I Resign my Board Seat?
Dear SaaStr: I am leaving a startup I co-founded on good terms with both the company and the remaining team. Should I resign my board seat? You should. If they…
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Q&A
Dear SaaStr: What’s The Top Early Sign a New Manager Won’t Work Out?
Dear SaaStr: What’s The Top Early Sign a New VP or Manager Won’t Work Out? There are quite a few: No one good wants to join them Don’t move out…
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Blog Posts, Early, Q&A, Sales
Dear SaaStr: What’s a Good Benchmark for B2B Sales Cycles?
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…
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Blog Posts, Fundraising, Q&A
Dear SaaStr: What Happens When a VC Loses All Their Money on a Startup Investment?
Dear SaaStr: What Happens When a VC Loses All Their Money on a Startup Investment? It’s a question being asked more often these days, unfortunately. And the answer? It’s OK…
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Blog Posts, Q&A
Dear SaaStr: What’s The Typical Enterprise SaaS Cancellation Policy For $100k ACV/Bigger Deals? Should The Contract Have a Fine?
Dear SaaStr: What’s The Typical Enterprise SaaS Cancellation Policy For $100k ACV/Bigger Deals? Should The Contract Have a Fine? Generally, just track to the cash: If a customer has signed…
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Blog Posts, Exit Strategy, Q&A
Dear SaaStr: What Do Most People Not Know About Acqusitions?
Dear SaaStr: What Do Most People Not Know About Acqusitions? That people, not companies, do acquisitions. “Amazon”, “Salesforce”, “Google”, etc. don’t buy companies. Executives do — to meet their goals…
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Early, Leadership, Q&A, Sales
Dear SaaStr: How Do You Handle Commissions if the Customer Auto-Upgrades for More Seats?
Dear SaaStr: How Do You Handle Commissions if the Customer Auto-Upgrades for More Seats? There’s no perfect answer here, but what most startups do is comp the sales rep for…
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Blog Posts, Q&A
Dear SaaStr: Why is Marc Benioff Complaining About Worker Productivity?
Dear SaaStr: Why is Marc Benioff Complaining About Worker Productivity? Because it’s an issue most of us are grappling with right now. Most startups and bigger tech companies are struggling…
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Blog Posts, Q&A
Dear SaaStr: What’s The Best Way to Improve Email Response Rates?
Dear SaaStr: What are the best ways to improve your email response rate for a SaaS sales startup? Slow it down. Email is amazing. CEO, CXOs, VPs and more read…
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Early, Leadership, Other, Q&A
Dear SaaStr: What Are The Biggest Challenges For a Non-Technical Founder?
Dear SaaStr: What Are The Biggest Challenges For a Non-Technical Founder? Adding enough value the first year. If you can’t build it, can you: Sell it? That’s worth it. If…
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Blog Posts, Early, Fundraising, Leadership, Q&A
Dear SaaStr: Why Do Venture Capitalists take Board Seats?
Q: Dear SaaStr: Why Do Venture Capitalists take Board Seats? It took me a while to figure this out. When I started writing venture (vs. angel) checks, the last thing…
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Blog Posts, Early, Growth, Q&A, Sales
Dear SaaStr: As a Founder, What Will I Learn Getting More Involved in Sales?
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…
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Blog Posts, Compensation, Q&A
Dear SaaStr: What Percentage of Software Sales Reps Have Earned Over $1m a Year?
Dear SaaStr: What Percentage of Software Sales Reps Have Earned Over $1m a Year? It’s rare and it’s tough in SaaS as a sales rep to earn a fairly stunning…
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Blog Posts, Career Growth & Advice, Customer Success, Customer Success, Growth, Q&A
Dear SaaStr: What Do You Do With Churned Customers?
Dear SaaStr: What Do You Do With Churned Customers? You put them into a Get Them Back bucket and re-market to them with a dedicated program. And you have sales…
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Company Culture, Early, Leadership, Q&A
Dear SaaStr: How Do You Know When It’s Time to Leave Your Current Company and Move On?
Dear SaaStr: How Do You Know When It’s Time to Leave Your Current Company and Move On? There are a lot of valid reasons to leave your job for a…
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Blog Posts, Featured Q&A, Fundraising, Q&A
15+ Due Diligence Questions You Really Should Be Asking Every VC You Meet
If you really want to diligence a VC, Talk to the CEO of a portfolio company not listed on their twitter — Jason ✨Be Kind✨ Lemkin (@jasonlk) August 16,…
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Popular Q&A
15+ Due Diligence Questions You Really Should Be Asking Every VC You Meet
https://twitter.com/jasonlk/status/1295136982658461697 Q: What is the proper way to do due diligence on a VC firm? Here are the things, IMHO and IME, that are most important. First, if you want to do it right, you should diligence both (1) the firm and (2) the...
The 3 Types of Day 1 Pricing: Low End of Normal. Identical. And Anchor High.
Q: As an entrepreneur starting out, is it better to overprice your product or underprice it? I remember years ago I was at an event with the CEO of a SaaS leader. And I asked him how he came up with their freemium pricing model. A data science team? A/B Testing? "No....
7+ Tips On How To Build Your First Sales Team
Q: How do you structure a sales team when you’ve got zero experience doing sales? Well, first go get some experience with sales. 🙂 At least, close the first 10 customers yourself. If you don’t, you’ll never have any idea how to do it. And the odds your first rep...
Why SMB Reps Struggle in the Enterprise. And Vice-Versa.
Q: How is low/mid-ticket sales different from enterprise sales? They are very, very different. If I had to boil down how to filter potential sales professionals based on just 1 controlling criterion, it would be deal size. Enterprise sales: Reps often hunt many of...
The Top 50 SaaStr Answers on Quora in 2020
It's been a fun experience being on Quora for ... a decade 🙂 We've crossed 60,000,000 views of our answers there, so let's take a look at the Top 50 most viewed SaaStr Answers on Quora in 2020: Why do many startup owners sell...
7+ Tips On How To Build Your First Sales Team
Q: How do you structure a sales team when you’ve got zero experience doing sales? Well, first go get some experience with sales. 🙂 At least, close the first 10 customers yourself. If you don’t, you’ll never have any idea how to do it. And the odds your first rep...
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