Dear SaaStr: What’s a “Messy Cap Table?” And How Do I Fix It?
Dear SaaStr: What’s a “Messy Cap Table?” And How Do I Fix It? A “messy cap table” refers to a capitalization table that’s overly complicated, disorganized, or structured in a way that creates problems for the company, especially when...
Dear SaaStr: Should You Hire Sales Reps in Pairs To Test Them?
Dear SaaStr: Should You Hire Sales Reps in Pairs To Test Them? Ideally, yes. Yes, you absolutely should hire sales reps in pairs, especially early on. Here’s why: When you hire just one sales rep, you won’t learn anything. Not for sure. If they fail, you won’t know...
Dear Should: Should Sales Execs Do Implementation Themselves?
Dear Should: Should Sales Execs Do Implementation Themselves? Almost never — outside of the earliest days. Your first 1 or 2 reps may have literally no one else to help here, and they often have to do the onboarding and implementation themselves. But you...
Dear SaaStr: How Important Is a Strong LinkedIn Presence Today?
Dear SaaStr: How Important Is a Strong LinkedIn Presence Today? Look there are few folks out there more skeptical and critical than me on folks that waste their entire day on LinkedIn. Go do the real work, folks. 🙂 And way too many folks are selling snake oil on...
Dear SaaStr: How Do I Structure a Comp Package for Our First VP of Sales?
Dear SaaStr: How Do I Structure a Comp Package for Our First VP of Sales? He’ll have 7 folks under him, For a small SaaS company with a Head of Sales managing 7 FTEs, I’d recommend a compensation structure that aligns with both early-stage SaaS norms and your...
Dear SaaStr: What Incentives Are Given To Design Partners and Other Super Early Customers?
Dear SaaStr: What Incentives Are Given To Design Partners and Other Super Early Customers? Design partners are critical—they provide feedback, validate your product, and often become your first case studies. At least … if they are real customers, and not...
Dear SaaStr: What Are Signs It’s Finally Time to Move on From An Employee?
Dear SaaStr: What Are Signs It’s Finally Time to Move on From An Employee? "When you make a bad VP hire, it's always your fault as CEO, not theirs. The candidate can never do enough research to understand if it's really the right fit."...
Dear SaaStr: What Are the Different Types of “Commits” Each Sales Rep Should Make?
Dear SaaStr: What Are the Different Types of “Commits” Each Sales Rep Should Make? The forecasting stages for a rep typically break down into three key categories: **Commit**, **Most Likely**, and **Best Case**. Bigger companies sometimes use more categories, but...
How To Do a QBR (Quarterly Business Review) Right
Dear SaaStr: How Do I Do a Good QBR (Quarterly Business Review) With Customers? It’s a great question as QBRs have in many cases degenerated into upsell meetings, with zero value for the customer. That’s not what you want. More on that here” The...
Dear SaaStr: We Have A Less Than 30 Day Sales Cycle. How Long Should We Give Reps to Scale Up?
Dear SaaStr: We Have A 30 Day Sales Cycle. How Long Should We Give Reps to Scale Up? With a sales cycle of less than 30 days, you should expect a new sales rep to ramp up **within 1-2 sales cycles**—so about 30-60 days. Here’s why: 1. First Sales Cycle (30 Days): A...
Dear SaaStr: My Sales Rep is Grossly Underperforming but is Involved in a Key Deal. Should I Fire Him or Wait for The Deal to Close?
Dear SaaStr: My Sales Rep is Grossly Underperforming but is Involved in a Key Deal. Should I Fire Him or Wait for The Deal to Close? This is pretty common and most founders make the same mistake. Move on from the rep now. There is almost no chance he is adding value...
Dear SaaStr: How Can I Get Outbound Going From Scratch in 30 Days?
Dear SaaStr: How Can I Get Outbound Going From Scratch in 30 Days? 30 days is a tight timeline, but it’s doable if you’re laser-focused. Here’s how I’d structure the next month to ensure you’re refining your outbound motion and getting those first meetings on the...
Dear SaaStr: Is It Still Important Today To Have a Phone Number On Your Website?
Dear SaaStr: Is It Still Important Today To Have a Phone Number On Your Website? Yes, absolutely. You should put a phone number on your website for prospects to call. It’s one of the simplest, yet most effective ways to build trust and credibility with potential...
Dear SaaStr: I’m at $5m ARR. Should I Hire a CRO?
Dear SaaStr: I’m at $5m ARR. Should I Hire a CRO? No, you need a VP of Sales, not a CRO. But … in today’s world, sometimes you have to allow for a little title inflation. If they will be a hands-on sales leader, but just want the title, sometimes...
Founder SaaStr
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