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Dear SaaStr: What’s The Number One Challenge for Scale-Up Stage Founders?

SaaStr

In SaaS, once you have even a few million in ARR, the #1 challenge is recruiting top-tier VPs and building a truly top-tier management team: SaaS products mostly don’t sell themselves. You can hack managing and finding 1–3 reps yourself, but after that, you really need a VP of Sales. She can be your CTO forever.

Scale 243
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Startup CTO or Developer

TechEmpower SaaS

Should a startup CTO spend their time programming? Here’s a graphic from Socal CTO that illustrates the roles as they change over time: In its earliest days, a startup’s top need is often to produce a product. Hiring a hands-on lead developer might seem like the right move for an early stage startup. What does the role demand?

CTO Hire 390
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What’s The #1 Challenge After $1m-$2m ARR?

SaaStr

In SaaS, it is recruiting your VPs and management team : SaaS products mostly don’t sell themselves. You can hack managing and finding 1–3 reps yourself, but after that, you really need a VP of Sales. You’ll need more than 5–6 core engineers to go big. Q: What’s the number one challenge for scale-up founders?

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Everything is Sort of the Same at a Given ACV (Annual Contract Value)

SaaStr

As you try to hire up for your SaaS company, you’re going to be faced with a lot of choices and trade-offs. No hire is the perfect package. But there’s one thing I can tell you in SaaS, at least: Almost Everything Except the Product Itself is Sort of the Same at a Given ACV (Annual Contract Value) Level.

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How to Hire A Great VP Sales: The Full Video and Transcript

SaaStr

As part of that, we wanted to look back at some of our most iconic content and sessions. One of the first what How to Hire a Great VP of Sales at the New York Enterprise Tech Meet-Up (thank you to John Lehr and Work-Bench for setting this up). I’m doing this thing for the first time. SaaStr is Turning 10!

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What were 5 distinct milestones that you encountered on the road to becoming a CEO?

SaaStr

We then had our own mini rocketship, hitting challenges and being acquired, and then being part of an IPO. But I got to part of the management team and make mistakes, and work cross-functionally with the other leaders and managers. But I started to learn what it took to recruit, inspire, and yes fail a team. I’m still learning.

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7 Pieces of Advice Entrepreneurs Never Hear That They Need to Hear with Jason Lemkin

SaaStr

1: Don’t hire a VP (or anyone in the early days) that you aren’t 95% sure is great. Founders between a million and $250M are talking about lowering the bar for hiring because they aren’t sure if the person is great or they’re trying to fill a gap. If you aren’t meeting that many, you aren’t taking hiring seriously.