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 —...
Dear SaaStr: What Kind of Background Checks Do VCs Do on Entrepreneurs They Fund? It varies. Everyone does some background checks, or least they did outside of the Boom Times of late 2020 through late 2021. And some do very in-depth ones with lots of “off sheet”...
Dear SaaStr: How Do Investors Feel About “Acquihires”? Back when I started investing, in 2013, VCs worked on getting acquihires for their struggling startups. A lot of energy was put in to find a “soft landing” for struggling investments...
Dear SaaStr: Did it ever take you a year to close a sale? Absolutely. This is pretty common in the enterprise. It took me about 18 months to close Google, for example. And that was just for the initial group of users: Need identification and discussions with...
Dear SaaStr: What Was the Toughest Rejection You Ever Had in Sales? The hardest rejection I’ve had in sales was around renewals. Especially ones I thought we really had earned. But still lost. In particular, in the early days of EchoSign / Adobe Sign, we had a...
Dear SaaStr: Is It Normal for a Founder CEO to End Up With Just 10% Equity? Yes — if you are venture-backed. Roughly speaking, this is what generally will happen after 3 rounds of traditional venture capital. Expect it and plan for it. If the company sells...
Dear SaaStr: What Should Happen When a Co-founder Wants to Quit? This is one of the toughest situations to be in. First, figure out if it’s just anxiety. Starting something is hard. Getting to the first $1m in ARR is borderline impossible. If it’s “just” anxiety, and...
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...