If Your VP Sales Isn’t Going to Work Out — You’ll Know in 30 Days
New SaaStr Fund portfolio company CRO his first week on the job: Note: he also started before he started. We’ve talked a lot on SaaStr about how to make that critical hire: the VP Sales. I’ve done it right, and I’ve done it wrong. When it’s...
What Happens When You Hire the Wrong VP
A lot of classic SaaStr content has been how to spot the best potential VPs. When to hire them. How to interview them and qualify them. What they really do. Etc. etc. Some classics here: How My VP, Sales Doubled Our Sales in 90 Days. And No, It Wasn’t Magic. If...
9 Signs a Startup Isn’t Going to Make It with SaaStr CEO Jason Lemkin
In a recent Workshop Wednesday, SaaStr Founder and CEO, Jason Lemkin sat down to discuss 9 signs a startup isn’t going to make it.
Hiring Risks vs. Hiring Flags. Make Sure You Get it Right.
My biggest hiring mistake I've made past 5 years that I never made before: I hired folks who didn't really, really, really want the job So far, none have worked out — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) April 16, 2025 During the Boom Times of...
The Best Sales Execs Are Great at The Interview Process, Too
If a sales exec makes it anything but effortless to schedule a job interview with them, Basically it won't work out — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) February 13, 2024 So I remember years ago I went to hire my first VP ever. To make it even tougher,...
The One Secret Tip To Hiring a Great Sales Rep (In The Early Days)
We’ve written this point before, embedded in other posts. We’ve talked about it in many presentations. But it’s time to call out One Simple Hack to getting sales going in your B2B start-up, in the early-ish days. One of the best there is in B2B....
Should You Fire an OK-but-Not-Great VP of Sales? Probably Not (Updated)
I wrote a version of this post some time ago, and I think it’s really one of the most important posts on SaaStr of all time, so I wanted to update it, especially in these times of more scrutiny and less capital. Because many of you are wondering … should...
Dear SaaStr: What Sales Comp Plan Should I Use For Our Very First Sales Rep?
Dear SaaStr: What Sales Comp Plan Should I Use For Our Very First Sales Rep? At the end of the day you have to solve for two things: A plan that gives the reps a living, fair wage; and A plan that you know and feel is accretive to the company. Sales reps have to be...
Dear SaaStr: What’s the #1 Most Important Thing To Look For In Your First Sales Rep?
Dear SaaStr: What’s the #1 Most Important Thing To Look For In Your First Sales Rep? The #1 most important criterion for your first 2 reps is: would you buy from her? For real? Would you truly, 100%, buy your own product from them? 98% of the reps you interview …...
Dear SaaStr: What is The Biggest Pain for a CEO?
Dear SaaStr: What is The Biggest Pain for a CEO? Competition is stressful. Raising funding can be hard. Partnerships can be frustrating. But the hardest part is always recruiting. And it never gets easier, not really. Every CEO I see past $2m in ARR or so, be it...
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”....
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