Yes, Your VP of Sales Also Has to Be a Great Salesperson Themselves
A mistake many founders make is hiring a VP of Sales who has many strengths — but is not great at selling themselves per se. A VP of Sales who is smart, polished, and worked at the right place, in a management-level position. That can talk about quota...
Dear SaaStr: What Are The Top 3 Criteria for Hiring Your First Head of Sales?
We’ve talked a lot on SaaStr about hiring that first VP of Sales. But what if you can’t find the right person, and you’ve spent months looking? What risks should you take when you’ve realized Ms or Mr Perfect just isn’t going to happen...
Dear SaaStr: How Long Should a CEO Continue Being the Head of Product?
Dear SaaStr: How Long Should a CEO Continue Being the Head of Product? Roughly — only for as long as it’s about a 10-hour a week job. Or often, maybe only up to $3m-$5m in ARR or so. These days, especially, I see way too many B2B companies at $8m-$10m ARR or beyond...
Dear SaaStr: What Were The First Five Hires You Made After Product-Market Fit?
Dear SaaStr: What Were The First Five Hires You Made After Product-Market Fit? My first 5 hires at Adobe Sign / EchoSign, beyond the core founding+ team, once we had paying customers and first, if early, product-marketing fit: #1: Full-time sales rep at $8k-ish MRR....
Dear SaaStr: How Many Options Should I Give to the First Non-Founder Employees?
Dear SaaStr: How Many Options Should I Give to the First Non-Founder Employees of they are making below market but non-zero salaries? Here’s the tough part. It’s really hard. What you should do is give them say 3x their forgone salary in stock — 3x to account for...
Dear SaaStr: What Did You Do in Your Startup That Didn’t Scale?
Dear SaaStr: What Did You Do in Your Startup That Didn’t Scale? My list is a bit quirky, but perhaps it will help a few others to accelerate — or drop — a few things: Doing international customer support myself. For months, I did European customer support myself...
Dear SaaStr: How Do You Draw The Line Between Founder and First Employee?
Dear SaaStr: How Do You Draw The Line Between Founder and First Employee? I’d suggest if you’re not sure where to draw the line … maybe don’t. It should be obvious. Founders are “there” before there is anything. Before a name. Before a product idea, usually. Before a...
Carta: Co-Founder Break Ups Are Accelerating. 23% Now Leave Within 3 Years. 30% Within 5. 35%+ Within 7. And The Numbers Are Going Up.
The Brutal Math of Co-Founder Breakups: What 22,000+ Founding Teams Tell Us About Your Odds If you’re building a 2-3 person founding team, there’s a 23% chance one of your co-founders will leave within the first 3 years. And that number is getting worse,...
Outbound Always Works. If You Do It Right. And You Put In The Time.
"Crummy outbound may not work that well these days. But great outbound still works like magic." pic.twitter.com/DwjcgRLOVA — Jason ✨👾SaaStr 2025 is May 13-15✨ Lemkin (@jasonlk) January 31, 2025 These days, it can really feel like the Old Bag of Sales...
Eventually … Almost Everyone Has a Sales Team
Eventually … everyone goes a bit enterprise Eventually … everyone adds a sales team https://t.co/6h3LesrvRo — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) October 16, 2025 The lure of freemium (like The Force) is strong. No headaches. Customers try and...
That Super-Successful VP of Sales. Great? Or Just Lucky?
I get sent this resume to review all the time. Director+ of Sales at Slack / Zoom / Mongo / Datadog / Qualtrics Your Brand Name SaaS Company. Took Hot Start-Up from $0 to $50m as VPS from Day 0. Was there “early” through IPO and did amazing things. That all sounds...
Dear SaaStr: How Does a First Time Founder Identify 10x Hires?
Dear SaaStr: How does a First Time Founder Identify 10x Hires? How do you hire a great CTO, a great VP of Product, a great VP of Sales … if you’ve never worked with one? It’s hard. If you haven't worked with one before, then, yes, 10x engineers...
Dear SaaStr: What’s The Toughest Skill to Learn to Scale in B2B?
Dear SaaStr: What’s The Toughest Skill to Learn to Scale in B2B? You need to learn to become a parallel recruiter. To constantly, painfully, boring-ly be recruiting the next level of management and managers — all the time. Doing 30+ interviews a month — minimum....
Dear SaaStr: Should SaaS Startups Really Have CROs or COOs? Is That Too Many Management Layers?
Dear SaaStr: Should SaaS Startups Really Have CROs or COOs? Is That Too Many Management Layers? A few years ago, I would have said No. There’s no way a SaaS startup needs a “CRO” or “COO” or other C-level Officers Without a Clear, Single Functional Area to Own Until...
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