Dear SaaStr: How Do You Compensate Reps on Multi-Year Deals?
Dear SaaStr: How Do You Compensate Reps on Multi-Year Deals? In the early days, when Cash is King, pay the sales reps a full commission on all cash paid up-front. It’s what I did. 95% of the time, this is what you want to do. As as a SaaS founder, I paid...
Dear SaaStr: How Do You Steal Customers From the Leader in the Space?
Dear SaaStr: How Do You Steal Customers From the Leader in the Space? There are so many products I would buy if the vendor just said "I'll do all the work for you" Instead, they all just want to tell me why they are 10x better But not really help me:...
Dear SaaStr: What’s the Best Advice Founders Never Hear?
Dear SaaStr: What’s the Best Advice That Entrepreneurs Never Hear? My list of top advice founders never hear: Slow it down if you don’t have a great co-founder. We all get excited to “get going” with a start-up. But if your co-founder isn’t great, if they don’t...
Dear SaaStr: How Should I Specialize My Sales Team?
Dear SaaStr: How Should I Specialize My Sales Team? If you’re asking the question, then the answer is probably yes 😉 One thing is clear: most founders and VPs of Sales and CROs look back and wish they’d specialized their sales team earlier. And not have...
Dear SaaStr: We Have a Sales-Led Motion and SMB Customers And The Economics Aren’t Working
Dear SaaStr: We Have a Sales-Led Motion and SMB Customers And The Economics Aren’t Working. What Do You Suggest? You have to be ruthlessly efficient with a sales-led SMB motion. It can be done: Toast does it at a $10k ACV with fairly low gross margins: Slice...
Dear SaaStr: How Do I Learn to Close Big Enterprise Deals … Better?
Dear SaaStr: How Do I Learn to Close Big Enterprise Deals Better? Closing high-ticket enterprise deals is a different beast compared to SMB or mid-market sales. It requires patience, strategy, and a deep understanding of the enterprise buying process. In fact,...
Dear SaaStr: When Should We Start Pushing For Multi-Year Contracts?
Dear SaaStr: When Should We Start Pushing For Multi-Year Contracts? For most of us: stop pushing for them in the Age of AI. The market has shifted, and fighting it costs you more than it gains. Here’s the reality: shorter contracts are now the norm across B2B +...
Dear SaaStr: We Lost an Enormous RFP Because We are Too Small. Any Advice?
Dear SaaStr: We lost an enormous RFP because we are too small. Any advice? This is indeed a big bummer. But it truly does make you stronger. If you commit to winning the next one. Six thoughts on how to do better next time: First, move them into your Lost Now (But...
Dear SaaStr: Is it OK to Modify the Standard SAFE Form?
Dear SaaStr: Is it OK to Modify the Standard SAFE Form? Ideally don’t. If you do — at least be transparent and crystal clear on what changes you are making. SAFEs require a high degree of trust to work. Hiding changes undermines that trust....
Dear SaaStr: Do Any Top B2B Events Give You “The List”?
Dear SaaStr: Do Any Top B2B Events Give You “The List”? No, no good ones do, and for good reason. Top tier B2B events, especially ones focused on quality over volume, deliberately don’t hand over attendee lists to sponsors as a blanket data asset. If...
Dear SaaStr.ai: At What Point Should We Hire an Internal Recruiter?
Dear SaaStr.ai: At what point has a start up do you hire a recruiter internally versus paying recruiters 20% fees? Hire a full-time internal recruiter once you’re hiring 5+ people per quarter consistently. Here’s the math: If you’re paying 20%...
Dear SaaStr: Should Both Founders Come to VC Pitches?
Dear SaaStr: Should both founders be at investor pitches, or just one is one? Both own 50% BTW. The CEO should always be at every VC pitch. The other founder? It is nice to have them there, especially if she or he can answer certain questions (e.g., product,...
Dear SaaStr: How Do We Reduce Churn?
Dear SaaStr: How Do We Reduce Churn? Churn is one of the most critical metrics in software. Maybe really the most critical in the end. With too much churn … in the end, it just doesn’t compound. It’s the silent killer of growth. You can’t scale...
Dear SaaStr: Our VC Is Encouraging Us to Hire Aggressively and Increase the Burn Rate. Should We Listen to Them?
Dear SaaStr: Our VC Is Encouraging Us to Hire Aggressively and Increase the Burn Rate. Should We Listen to Them? In my experience, about 66-70% of the time this is bad advice, especially if it is coming from a Very Large VC. Not always. But more often than not. Why?...
Founder SaaStr
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