Dear SaaStr: As a CEO, How Do You Know That Your New Employee is an A,B, or C Player?
Dear Saastr: As a CEO, How Do You Know That Your New Employee is an A,B, or C Player? You might not at first. So get help. But you’ll get better at this. As a first-time manager, you really won’t have the experience to know really who is an A, B or C player for any...
Dear SaaStr: How Do We Close Bigger Deals?
Dear SaaStr: How Do We Close Bigger Deals? If you already have a few bigger deals under your belt, but most are smaller … a few higher-level suggestions: #1. Hire a Very Good VP of Sales that has sold at your “high end” price point. They will be much better at you...
If You’re Going to Stick with a Mediocre VP for Now, You At Least Have to Micromanage Them
I know this is advice you probably don’t want to hear. We’ve all been told that micromanagement is bad. That great leaders hire great people and get out of their way. That autonomy is the secret to building high-performing teams. And that’s 100% true. For...
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”....
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....
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