We just wrapped SaaStr AI Annual 2026, and the closing Q&A on Day 3 ended up being one of the most engaged of the whole gathering. No script, no prepared deck, just an hour-and-a-half of questions from the audience on the topics most on their mind. We went off on a lot of tangents. Some…
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Dear SaaStr: How do I Convince My CEO that Marketing is Important? A lot of CEOs these days do seem to be late to truly invest in B2B marketing, and most especially, to hiring a true VP of Marketing. In the Age of AI, so many CEOs hack it to $5m, $8m, $20m+ in ARR…
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Dear SaaStr: How Do I Know If My New VP of Marketing Is Going To Make It? Dear SaaStr: How Do I Know If My New VP of Marketing Is Going To Make It? You’ll know pretty quickly if a new VP of Marketing is going to make it, or not. The best ones deliver…
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Dear SaaStr: Should a Startup Founder Handle Sales Themself When First Getting Started? The answer is yes – 95% of the time. The “best” sequence for building a repeatable sales engine is roughly: The CEO/founder should close at least the first 10 (or 20 or whatever) customers. That way, she knows. She knows the process,…
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Dear SaaStr: How Long Does It Take the Average B2B Startup to “Exit”? I took a look a little while back at how long it took the average SaaS company that was sold for $1B+ to get that acquisition. The answer? 11.7 years on average, with a median of 10.0 years (maybe the better metric):…
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Dear SaaStr: What Are The Top Things to Know Before Starting a B2B Startup? A lot of founders ask this question hoping to hear something they don’t already know. The honest answer is the opposite. The hard truths about starting a B2B company are mostly things you already suspect but haven’t fully accepted yet. Accept…
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Dear SaaStr: I’m a Seed Stage, First Time VP of Sales. What Should I Do To Be Successful? First, congrats. That said, I have to give you the hard truth before the playbook: most first-time VPs of Sales hired at seed stage fail. Not because they’re bad. Because the role itself is set up to…
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Dear SaaStr: What are some common reasons that CEOs and other top executives are fired? Ironically, it is rarely for missing the plan — at least at start-ups. Rather, execs and CEOs are fired for (x) hiding that they are missing their plan, and (y) blaming others. The reality is VCs and board members know…
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Dear SaaStr: How Long Should I Wait to Follow Up After A Big Customer Pitch? You shouldn’t wait at all. Follow up immediately after the initial pitch meeting. Ideally, within the same day. The best always do. If you can’t do it that quickly, make sure it’s no later than 24 hours. Here’s why: 1. Momentum Matters…
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Dear SaaStr: How Do I Know If It’s The Right Time to Sell My Company? First off, the axiom that companies are bought, not sold, is mostly right. 95 times out of 100, you can’t wake up some morning and just go sell your start-up. Unless there are pre-existing relationships that have expressed a desire…
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Dear SaaStr: When Do You Start to Develop a Brand in SaaS? In my experience, probably as early as $2m worth of happy customers. At least the beginnings of a “mini brand”. At that point, you don’t have a world-famous brand or anything. But you do start to have a “mini-brand”, where folks in your…
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Dear SaaStr: When and how should SaaS startups offer reduced pricing vs the competition? For most B2B apps, you want to at least start with “just right”, Goldilocks pricing: #1. Too high a price, and you start to add friction to the sales process. Deals take longer, leads shop other vendors, etc. That may be…
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Dear SaaStr: I’m Joining a B2B Startup at $3m ARR as VP of Sales. What Should I Do First? Stepping into the VP Sales role at a company with $3M ARR is a pivotal moment. At this stage, the company has likely found some product-market fit, but scaling efficiently and predictably is the next big…
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Dear SaaStr: What sales techniques helped you consistently succeed while others failed? A few that basically always work in sales … but that so many don’t do actually do: Being a product expert. 95% of the sales execs I talk to in software don’t know the product much at all. A huge miss as half…
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Dear SaaStr: I am a startup founder that writes extensive monthly report to investors. We are also doing weekly meetings, are they asking for too much of my time? Yes, that’s too much. Some rough rules: For every 1% of a company an investor owns, they get one meeting / Zoom a year until you…
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Dear SaaStr: What’s considered a large amount of money for an investor? The answer isn’t obvious from the outside. And it’s something founders should know. Is $1m a lot? $100k? $20m? It really varies by VC and by fund. A rough answer is investing more than 1.5%-2% of an individual fund into one deal is a…
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Dear SaaStr: What Sales Comp Plan Should I Use For Our Very First Sales Rep? At the end of the day you have to solve for two things: A plan that gives the reps a living, fair wage; and A plan that you know and feel is accretive to the company. Sales reps have to…
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Dear SaaStr: How Long Should You Give a New Sales Rep? The tough truth is from 0.5–1.5 sales cycles. And yes this is true even in tougher times. Probably even more so in tougher times. Sales is tough. It’s a lot of Nos to get to a Yes. And while sales is pretty similar in…
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Dear SaaStr: What Was Your Very First Sales Story? How Did It Go? My very first sales deal was for $6,000,000. In my first start-up, I was mostly hunting whales — seven-figure and eight-figure deals. I had no experience doing any of this. For our First Big Customer, we’d been negotiating a $6m/year contract for…
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Dear SaaStr: How Do I Know If My New VP of Marketing Is Working Out? It’s tough. Way too many senior marketers today just want to be strategists. Or just manage a few agencies and work on brand. That’s not what you need. You’ll know if your VP of Marketing is working out by looking…
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Dear SaaStr: Should I Remove Monthly Subscriptions to Drive Down Churn? Generally — no. Annual plans only mask churn. They don’t eliminate it. And at least for SMBs and prosumer customers, not having a monthly edition can add significant friction to buying. That means less customers & less sales. I’s a double-edged sword. It simplifies…
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Dear SaaStr: Should We Over-Charge or Under-Charge our First Customers? My general rules: Overcharge if the customer is big, i.e., >$50k-$100k a year o nor so in ACV. Undercharge if the customer is smaller by revenue. There’s a method to the seeming madness here. You’re learning very quickly here if you are enterprise or mass-market…
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Dear SaaStr: What’s It Like to Have Your Company Acquired by One of the Tech Giants? It’s a lot of change. The pressure is mostly or at least partially off. Unless there is a huge earn-out or retention payment tied to performance, the pressure is off. Not all of it. But the insane founder-CEO pressure you…
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  Dear SaaStr: How can I boost my sales if I am in B2B sales? My top tips for AEs: Grab your CEO and bring her into bigger deals. Ask your CEO to join you on a few sales calls a month. Deals will close at a higher rate if the CEO joins. Customers love…
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The biggest mistake you can make as a founder when you hire your first VP of Sales is stepping out of sales I see this again, and again It only works with the very best VPs of Sales Every other first VP of Sales needs you doing at least half of what you were doing…
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