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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 262
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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. She can be your CTO forever.

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

SaaStr

To hire our CTO, our first VPE, etc. And to close $6m in customer contracts through founder-led sales. Bootstrapping is far better. But if you do need to raise money, it’s the CEO that has to do it. And I learned to recruit. I’m still learning. View original question on quora.

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Dharmesh Shah of HubSpot: From Day 0 to IPO. What Went to Plan. What Most Certainly Didn’t (Video, Podcast + Transcript)

SaaStr

Co-founder and CTO Dharmesh Shah shared with us how they got there — and the top mistakes they made — just 3 quarters after their IPO. We have someone that probably 98 percent of you know virtually or socially in some sense, Dharmesh Shah, founder and CTO of HubSpot. ” We didn’t do any annual contracts.