CTO Hire Part-Time VPE Scaling 
SaaStr
MAY 3, 2025
Dear SaaStr: From 0 to $10m ARR, At What Point Do We Start Hiring and Whom? From 0 t o $ 10M ARR, the hiring roadmap is critical because every hire has a disproportionate impact on your trajectory. No VP of Sales yetdont even think about it. Marketing : Likely no VP of Marketing yet either — unless.
SaaStr
JANUARY 9, 2025
Every time I see a CRO that doesn't sell themselves, they fail. Every time I see a CTO that doesn't code themselves, they fail. Every time I see a CMO that doesn't market themselves, they fail. We’ve spend the most time on hiring a great first VP of Sales, but all the VPs are super important.
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SaaStr
NOVEMBER 19, 2020
IME, rough order to make hires in: VPM: $0.2m ARR VPS: $1-$1.5m ARR VPCS: $2m ARR VPP: $3m-$4m ARR VPE: $5m-$6m ARR CFO: $10m ARR COO: $20m ARR. He’d found several good First VP candidates, in particular, a strong first head of marketing and a strong first head of product. He asked which to hire first.
SaaStr
SEPTEMBER 10, 2020
Perhaps the single most important thing you can ever do in SaaS, at least after $1m in ARR or so, is hire the best VPs you can. 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. Check who they hired.
SaaStr
JANUARY 19, 2022
Dear SaaStr: What Makes a Bad CTO? While there is no legal definition for CTO or bright line between CTO and VPE, I’d suggest a start-up CTO really only has to do a few things — which are very hard: Assemble a small team (3–9) of very good engineers. A “bad” CTO doesn’t care about growing very, very quickly.
SaaStr
MARCH 1, 2024
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.
SaaStr
JUNE 23, 2020
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. You’ll need more than 5–6 core engineers to go big.
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