Dear SaaStr: What’s The Best Way to Fire Your Co-Founder Who Was Once a Friend? It’s pretty common that a co-founder doesn’t work out, unfortunately. I’ve been a part of all versions of this: I’ve had a great co-founder that went the distance with me. I’ve had one that quit less than a year into…
Continue Reading

Dear SaaStr: What Are Some Signs That Your B2B Marketing Programs Won’t Scale Well? The #1 flag your marketing efforts aren’t working is that you are spending too much — but importantly, in the aggregate. Don’t overindex on any individual campaign or initiative. Let me dig in a bit. Most B2B companies, once they have…
Continue Reading

Dear SaaStr: Why Do Many Startup CEOs Quit After Their Companies Are Acquired? Five reasons: First, it’s very difficult for most founder-CEOs to work for someone else. They generally don’t mind working with others. They don’t even need to be “the boss”. But being told what to do, especially when it’s not clearly “right”? Tough….
Continue Reading

Dear SaaStr: How Long is a Venture Round Supposed to Last? I think like many venture axioms, founders get often get bad advice here out of good solid rules. The classic rule was “18-24 months”. In boom times, it’s still true … it’s just the frenzy to get into hot deals means most VCs care…
Continue Reading

Dear SaaStr: Growth Has Slowed and My VP of Sales is Pushing Me To Hire More Reps. Is That The Right Way to Go? No. Not 9+ times out of 10. Probably 9.8 times out of 10. It’s a desperation move. In fact, the #1 sign your CRO / VP of Sales is really struggling…
Continue Reading

Dear SaaStr: How Do You Build a Real Exit Strategy? First, bear in mind acquisitions are relatively rare. The vast majority of startups will never get one strong acquisition offer. Still, it’s not random. I’ve been through it twice as a founder and about ten times as an investor. OpenRouter is joining Stripe: https://t.co/hiH0kDB3hG. As…
Continue Reading

Dear SaaStr: Can A Great Sales Rep Sell Any B2B Product? No. Not really in software. At least not well. Although many think they can. Too many. The very, very best in SaaS that are truly curious can often sell almost any product well. But this is a narrow group of the best of the…
Continue Reading

Dear SaaStr: One of Our Most Respected Team Members Quit and Folks Are Leaving. What Do I Do? Promote someone great that everyone respects into a leadership role. Right now. This is really the only answer I’ve seen to this situation. We’ve all been in it at least to some extent, at some level. Sometimes,…
Continue Reading

Dear SaaStr: I Was Fired Without Cause. Should I Tell My Story Publicly? I get it. In a sense, it happened to me — once. But I’ve learned a few things: No one cares. They really don’t. It can make you look a bit petty or weak (fair or not). No one wants to work with, or…
Continue Reading

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. It’s not attending QBRs. It’s making your number — quarter after…
Continue Reading

Dear SaaStr: Suppose the CEO of my competitor contacts me, interested in acquiring my app (privately owned). What steps would I take to avoid giving away proprietary information before the sale closes, if ever? Just meet. Meet all your competitors. You never know where it will go: It may help you head off a conflict…
Continue Reading

Dear SaaStr: What’s Your #1 Opener in Sales? The best opener is sharing how a very similar company or a competitor uses your product — and the exact specific ROI that customer gets. Everyone wants to know the playbooks of similar companies and competitors. How often does your sales team actually do this? Put in…
Continue Reading

Dear SaaStr: At What ACV Size Do I Need an Account Manager in B2B? There’s no hard rule, but here’s what the data shows: Below $8K-$10K ACV: You can’t afford dedicated account managers. You need to systematize onboarding and support instead—self-serve + a lean support team. The unit economics don’t work with humans doing 30+…
Continue Reading

Dear SaaStr: What Is A Good Demo Conversion Rate for a SaaS Startup? 10%-20%. If fewer than 8%-10% or so of your demos convert to paid customers, you’ll start to burn out your sales team. Because they generally need to close 10-15 deals a month to eat (more for SMB, less for enterprise, but 10-15…
Continue Reading

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 nothing on multiyear…
Continue Reading

Dear SaaStr: What are the most common mistakes founders make hiring their first real sales teams? A few key mistakes I see start-ups making > 50% of the time: Hiring Early Reps (#1 – #3) That You Personally Wouldn’t Buy From. Don’t hire someone with the right resume. Hire someone you’d buy your own product…
Continue Reading

Dear SaaStr: I Fired My VP of Sales. What Now? It’s tough and there may be some bumps. But honestly things probably will be better in just a week or two. What you do need to do is have a plan. You need to act fast and smart to stabilize and rebuild. Here’s what you…
Continue Reading

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: – buy out my…
Continue Reading

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 have the right skills to complement yours, and/or…
Continue Reading

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 everyone work in a round-robin or similar format on…
Continue Reading

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 does the same: As does Mangomint: As does…
Continue Reading

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, arguably … SMB sales and enterprise sales have almost nothing in common. More on…
Continue Reading

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 + AI, and it’s rational buyer behavior, not…
Continue Reading

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 Not Forever) Marketing…
Continue Reading

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. There’s an issue I see blow up several times now as…
Continue Reading