Beware the “Mediocre Recycled”. The Zombie Executives of B2B.
So this post isn’t meant to be a sub-tweet, or a sub-post — it’s just a general learning over the years. So please, no one take this personally. It’s not about you. But I’m still going to make one simple suggestion when you go to hire...
Dear SaaStr: How Can I Give Better SaaS Product Demos?
Dear SaaStr: How Can I Give Better SaaS Product Demos? One simple answer: train your reps more. A lot more. With most SaaS companies, for a while, demos get worse: At first, founders do all the demos. The demos themselves are a bit rambling, too long — but...
Dear SaaStr: We Are Growing Too Fast to Handle the Workload, but We Can’t Afford to Hire New Employees. Help!
Dear SaaStr: We Are Growing Too Fast to Handle the Workload, but We Can’t Afford to Hire New Employees. What’s wrong with our business model? Nothing. We’ve all been there. Almost all of us, at least. In SaaS, this typically happens somewhere between $3m...
The Top Reasons I Saw CROs Flame Out This Year
I saw about 10 CROs leave or get fired this year across the startups I work with or have invested in at SaaStr Fund. That’s a lot. That’s actually a ton. It may be a record. I suspect it is. And look, some CRO transitions are natural. The company...
Dear SaaStr: What’s the #1 Way I Can Accelerate My Career Growth?
Dear SaaStr: What’s the #1 Way I Can Accelerate My Career Growth? My uber-learnings: Find the best boss you can; and Take on every initiative, project, task, and endeavor you possibly can from her. And work for them for a while. Long enough to get promoted once,...
Dear SaaStr: For High Dollar Vertical SaaS, Does The 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...
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,...
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