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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 237
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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. Upsell and retention is an art, science and craft. You’ll need more than 5–6 core engineers to go big.

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What Happens When You Hire the Wrong VP

SaaStr

You know how everyone says you'll never look and wish you'd kept a bad VP as long as you did? That when you make a mis-hire, you'll always look back and say you should have made a change 3-4 month earlier? A lot of classic SaaStr advice has been how to spot the best potential VPs. When to hire them.

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From Initial Traction to Initial Scale (~$10M in ARR): The Hardest Phase. But — The Cavalry is Coming.

SaaStr

But it turns out, the hardest part isn’t the Magic and the Impossible. The hardest part is this phase: the Possible, But Painful. If your VPE, or head of marketing, or someone key quits — you’re almost dead. But if you hire one VP after another, it will just take way too long. So first, buck up.

Scale 250
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10 SaaS New Year Resolutions For You. Pick a Few.

SaaStr

Pick a few that work for you: Get That Key VP Hire Done in Q1. Enough with the excuses for not having hired your real VP of Sales, or that VP of Engineering, or whatever. Hire a real recruiter. Drop other stuff to get this hire done. But anyhow — in January, find a way.

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5 Interesting Learnings from Okta at $2.5 Billion in ARR

SaaStr

Founder CEO Todd McKinnon was VP of Engineering at Salesforce and left to start Okta in the depths of the last downturn. Customer Count Up 8% Year-over-Year to 18,950 It’s hard to find net net customers after $1B ARR. You usually have to start here, but as time goes on, you need to bring in partners in most cases. #7.

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5 Things to Do … When You Don’t Know What to Do

SaaStr

you don't know what to do: 1/ Spend more time w/existing customers. 2/ Hire 1 great VP. Those are good times indeed. But there will be times when almost all of just not only struggle … but are just sort of out of ideas. Spend more time with existing customers. Hire 1 great VP.