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. If you haven’t sold to the F500 / Global 2000 before, you’ll be somewhat surprised to learn...
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...
Dear SaaStr: What Successful Startups Were Launched While The Founders Worked 9 to 5? I’m not aware of any huge successes in SaaS that were active side projects while the founders worked at different companies. But there are a bunch that were side projects at the same...
Dear SaaStr: A Co-Founder is Asking for More Equity Post Fundraising. What Should I Do? Listen. It usually means something is wrong. Or at least, off: If you got the equity splits right at first, usually, big issues don’t come up later. This may be a sign you need to...
Dear SaaStr: Does valuation play into how likely anyone would want to acquire the business from the founders? Absolutely. A lot. There is no question “too high” of a valuation can discourage an acquisition. Acquirers will generally assume they have to pay more than...
Dear SaaStr: What’s the #1 Most Important Thing in Pricing A New SaaS Product? I think the #1 thing to think about is context. Software all sort of all, rough-and-tough, costs the same to build and ship. Why is Calendly $10 a month, when Salesforce is $200 a month...
Dear SaaStr: did you ever have a situation where you were talking to a person but that person turned out to be a billionaire? I’ve done OK, but I’ll never be a tech billionaire. However, I’ve met and worked with many (as crazy as that sounds to say “many”) in my...
Dear SaaStr: What’s the difference between a VP of Marketing and a VP of Demand Gen? Perhaps nothing. Perhaps. A lot of demand gen leaders want to be a “VP of Marketing” next, and that can be a great hire, and a great title to give them. But in...
Dear SaaStr: What’s The Number One Challenge for Scale-Up Stage Founders? In SaaS, once you have even a few million in ARR, the #1 challenge is recruiting top-tier VPs and building a truly top-tier management team: SaaS products mostly don’t sell themselves. You...
Dear SaaStr: What Would Be The Single Most Important Advice You Would Give Other Entrepreneurs? Quit today if you don’t want it bad enough. But … never quit if you truly do. … Now, by “quit” I don’t literally mean leave the keys on your...
Dear SaaStr: Does a Big Exit Make You Happy? Well here in the SF Bay Area … we live in a strange place. Folks I know with “infinite” money sort of fall into 3 buckets: Category 1: Still Building Stuff. For Whatever Reason. In their DNA. This is...
Dear SaaStr: What Is The Best Indicators of Product Market Fit at an Early Stage SaaS B2B Startup? This is a rough metric, but I’d say from experience working closely with 25+ SaaS companies … if you aren’t growing > 10% a month after $10k in MRR or so … then you...
Dear SaaStr: How much money do the best SaaS inside sales AEs make? You can back into it. Ultimately, in most SaaS startups, the sales reps will take home about 20% of the total deal value they close. Maybe 25% if SMB sales and/or a startup is very well funded. At...
Dear SaaStr: What does “old-school” series A funding mean? Most likely: trying to buy 15-20%+ of a company, that is reasonably capital-efficient, and has at least product-market fit and some early traction, that hasn’t done endless seed rounds before...
Dear SaaStr: What Is The Average Time it Takes a VC to Make an Investment Decision? For hot seed and even Series A investments? 20 minutes into the first face-to-face meeting. The average VC basically makes the initial decision to tentatively invest very quickly —...