Dear SaaStr: When Should I Vibe Code An App vs. Buy One?
Dear SaaStr: I keep hearing about “vibe coding” and founders building their own internal tools with AI. But we already pay for a bunch of B2B products. When does it make sense to vibe code something yourself vs. just buying an off-the-shelf product? Great...
Dear SaaStr: I Want to Roll Out an AI SDR. How Do I Start?
Dear SaaStr: I Want to Roll Out an AI SDR. How Do I Start? First, get clear on what you’re actually buying — and what it actually does. We’ve now been running AI SDRs at SaaStr for over a year. Multiple platforms. Real data. Real pipeline. And the honest...
Dear SaaStr: Do You Have to Have a Super Strong Brand Like SaaStr To Get AI SDRs to Work?
Dear SaaStr: Do You Have to Have a Super Strong Brand Like SaaStr To Get AI SDRs to Work? Honest answer: it helps. A lot. But it’s not the thing that determines whether you succeed or fail. Let me explain what brand actually does — and doesn’t — do for AI...
Dear SaaStr: Should I Run 20+ AI Agents the Way SaaStr Does?
Dear SaaStr: Should I Run 20+ AI Agents the Way SaaStr Does? The honest answer: probably not entirely like us. But you should start now — because the gap between teams who have been running agents for 12 months and those who haven’t is compounding every week....
Dear SaaStr: What’s the Best Way to Follow Up With a Prospect That Says “I’ll Get Back to You”
Dear SaaStr: What’s the Best Way to Follow Up With a Prospect That Says “I’ll Get Back to You” Let’s start with honesty: “I’ll get back to you” almost always means No — or at best, Not Now. That’s not cynicism....
Dear SaaStr: How Can I Become a Better VP of Sales?
Dear SaaStr: How Can I Become a Better VP of Sales? The hard truth: most VPs of Sales fail not because they can’t sell, but because they don’t understand what the job actually is. It’s not managing a team. It’s not building process decks....
Dear SaaStr: I Have a Final Interview for an SDR Role at a Top Vertical SaaS Company. How Do I Nail It?
Dear SaaStr: I made it to the final round for an SDR position at a leading vertical B2B company. The interview is with the Sales Manager. How do I prepare so I actually get this offer? First off — congrats. Making it to a final round SDR interview at a real vertical...
Dear SaaStr: We Have a $5M Acquisition Offer at $500K ARR. What Will Our VCs Think?
Dear SaaStr: We’ve raised $2M and our investors don’t want to put more money in. We’ve about 7 months of runway. An acquirer wants to purchase us for $4-5M. What will our VCs think of this outcome? I get versions of this question a lot, and I want to...
Dear SaaStr: Should I Take On Venture Debt?
Dear SaaStr: We’re at $4M ARR, growing well, and a lender is offering us $3M in venture debt. Our investors think it’s “non-dilutive capital.” Should we take it? Short answer: Maybe. But understand what you’re signing before you do....
Dear SaaStr: Is it Wisest to Approach One Investor at a Time?
Dear SaaStr: Is it Wisest to Approach One Investor at a Time? No. First, it takes too long. If a VC doesn’t know you, and you aren’t a “super hot” start-up, even if you do get a term sheet — it may take months. Yes, term sheets get done in one day. I haven’t done...
Dear SaaStr: My Investor Wants Weekly Meetings. Is This Too Much Time?
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. Some rough rules: For every 1% of a company an investor owns, an investor should get one meeting 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 potentially better one. But — if your job isn’t bad, and your boss is pretty good, it’s worth...
What’s It Really Like to Be CEO of a Startup
Dear SaaStr: What’s It Really Like to Be CEO of a Startup? Let me just throw out a few things I’ve learned that being a CEO of start-up isn’t, or isn’t as you’d expect: It isn’t glamorous until you are At Scale and Hot, at the very minimum. At...
Dear SaaStr: What is The Biggest Pain for a CEO?
Dear SaaStr: What is The Biggest Pain for a CEO? Competition is stressful. Raising funding can be hard. Partnerships can be frustrating. But the hardest part is always recruiting. And it never gets easier, not really. Every CEO I see past $2m in ARR or so, be it...
Founder SaaStr
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