Remove CTO Remove Sales Recruiting Remove Scaling
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The Top 10 Reasons to Attend 2025 SaaStr Annual, May 13-15 in SF Bay!!

SaaStr

The Best Speakers In The World With hundreds of sessions from proven SaaS leaders who have scaled companies to significant revenue milestones, SaaStr Annual offers practical, actionable insights you won’t find elsewhere. Finding and recruiting top talent is consistently ranked as one of the biggest challenges for growing SaaS companies.

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

SaaStr

Dear SaaStr: What’s The Number One Challenge for Scale-Up Stage Founders? 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 will need a VP of Product to scale your roadmap.

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VPs That Can’t Hire … They Aren’t Real VPs. At Least, Not Yet.

SaaStr

We’ve talked a lot over the years about how not to hire a wrong VP of Sales — 70%+ of the first VPs of Sales don’t make it even 10 months. And figure out if they really are great: For your prospective VP of Sales, did her top 2 hires at least crush it and blow out their quotas ? Recruiting.

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

SaaStr

Q: What’s the number one challenge for scale-up founders? 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. She can be your CTO forever.

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My 7 Biggest Mistakes as a SaaS Founder-CEO

SaaStr

I should have camped in his office and literally never taken No for an answer. I had a great CTO, but I also needed a truly great VPE to scale past $10m ARR and deal with all those issues. Our CTO was amazing, but we didn’t work together as well as we should of. Not becoming a better recruiter.

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10 Hacks to Have Happier Investors

SaaStr

Your investors and others will learn a lot more hearing about sales from your VP of Sales, your CTO co-founder … and not you. This also will make you appear to be a much stronger manager. Especially, don’t try to talk over your weakest VPs and managers. All-hands meetings, board meetings, whenever.

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10 Things That Would Have Helped Me Go From $1m to $10m Faster with Less Stress

SaaStr

I thought it would be worth drilling down deeper into each of them, and sharing the learnings and mistakes: 1/ Spending less time fixing things, more time recruiting senior folks to own them. No one spends enough time recruiting as it is, after $1m ARR or so. Yes, you can manage the sales team yourself. You can do this.