Dear SaaStr: How Do I Best Prevent Churn?
Dear SaaStr: How Do I Best Prevent Churn? You don’t. Instead, you drive it down. Each quarter. You can’t eliminate churn. It’s a fact of business life in selling a product with recurring revenue and thus recurring sales. You can hide churn (e.g., by signing multiyear...
Dear SaaStr: How Can an Early Stage SaaS Startup Get its First 1-3 Pilot Fortune 500 Paying Customers?
Dear SaaStr: How Can an Early Stage SaaS Startup Get its First 1-3 Pilot Fortune 500 Paying Customers? It’s not magic. And it’s not a mystery. Even though it can seem like it, until you’ve done it yourself. There are basically two paths, and one...
Dear SaaStr: What Was it Like Acquiring Your First Customer?
Dear SaaStr: What Was it Like Acquiring Your First Customer? I had very different experiences in each of my startups. In my first start-up, we were whale hunting — big, large, Fortune 500 customers. So Customer #1 showed us the path to our future. My first customer...
Dear SaaStr: How Would You Invest a 5 Million Dollar Payout From an Acquisition?
Dear SaaStr: How Would You Invest a 5 Million Dollar Payout From an Acquisition? Bear in mind I’m not a CFA, CPA, or professional financial advisor. But I have been through it. And so I know this is a more difficult question to answer than you might think. The...
Dear SaaStr: How Do You Deal With an Unreliable Co-Founder?
Dear SaaStr: How Do You Deal With an Unreliable Co-Founder? You first try to move them into an individual contributor role. If that doesn’t work, then move them out. This is one of the most frustrating outcomes, when a very talented co-founder becomes “unrealiable”....
Dear SaaStr: Why Do Most Entrepreneurs Under Price Their Offerings Initially?
Dear SaaStr: Why Do Most Entrepreneurs Under Price Their Offerings Initially? Yes, most of us at first under-price and then slowly raise prices as we gain confidence. It’s because (1) we aren’t trained sales leaders, and (2) we worry most about not losing the...
Dear SaaStr: How Can I Convince My Investor We’ll Double Their Investment By The Next Round?
Dear SaaStr: How Can I Convince My Investor We’ll Double Their Investment By The Next Round? It may be an odd & unusual question — but I think it’s a good one. If you are a VC / private investor, there’s a key meta question: why invest...
Dear SaaStr: How Do You Handle Customers That Want to Build It In-House?
Dear SaaStr: How Do You Handle Customers That Want to Build It In-House? Be “Cool”. What I mean is, we all go through this, at least, a lot of us. When you first build a start-up, it’s often feature-poor, with little-to-no brand. Internal IT teams sometimes think they...
Dear SaaStr: Why Are So Many VCs Grouchy These Days?
Dear SaaStr: Why Are So Many VCs Grouchy These Days? I think because it’s so damn hard to truly make money as a VC. So, so much harder than it felt in late 2020 and 2021: If you aren’t in the top quartile of venture fund performance at least, maybe...
Dear SaaStr: What Happens to the Management Team When a New CEO is Hired?
Dear SaaStr: What Happens to the Management Team When a New CEO is Hired? You never know exactly what will happen. However, at a practical level, I think you should plan on maybe 50% of the management team turning over if your company brings in a new CEO. Maybe more....
5 Lessons Learned from a 20+ Years Operator Turned First-Time Founder with ex-Synk and Elastic CMO Jeff Yoshimura
Jeff is the co-founder of a new stealth startup, a previous CMO at Snyk, and an operator at Elastic, Zuora, and Salesforce. His day-to-day role as a first-time founder involves a lot of work around creating and building the MVP product and filtering out all of the noise in this SaaS ecosystem. Now, Jeff shares five themes and his lessons learned over the past 6-8 months as a founder vs. an operator.
Dear SaaStr: Does the Fund Make The VC or VC Make The Fund?
Dear SaaStr: Does the fund make the VC or VC make the fund? The VC makes the fund — but it’s a little more nuanced than that. Only 2 things matters for VC until it’s late stage, and maybe even then: Getting the best founders to pick you; and Picking...
Dear SaaStr: For High Dollar Vertical SaaS, Does The First VP of Sales Need Domain Expertise?
Dear SaaStr: If you were hiring a head of sales for a high-priced, niche B2B SaaS product, would you focus on general B2B SaaS sales experience or on market/customer knowledge, assuming it will be very difficult to find a candidate with both? This is the scenario when...
Should You Hire a Sales Rep First, Or a Sales Manager?
Dear SaaStr: Should I Hire a Sales Rep First, Or a Sales Manager First? The ideal flow is: You (founder-CEO) close the first batch of customers, say the first 10 or 20. If you don’t, you’ll never really know how it’s done. Or be able to help anyone else, really. Then,...
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