Dear SaaStr: If you were hiring a head of sales for a high-priced, niche B2B SaaS product, would you focus on general B2B SaaS sales experience or on market/customer knowledge, assuming it will be very difficult to find a candidate with both? This is the scenario when...
Dear SaaStr: Should I Hire a Sales Rep First, Or a Sales Manager First? The ideal flow is: You (founder-CEO) close the first batch of customers, say the first 10 or 20. If you don’t, you’ll never really know how it’s done. Or be able to help anyone else, really. Then,...
Dear SaaStr: How Do You Take Care of Yourself As a Founder? Quiet quitting, feeling sorry for yourself, working 30 hours a week, etc. — that doesn’t really work for a founder. It may feel good in the short term, but it doesn’t work. It doesn’t get you to success. But...
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...