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Dear SaaStr: Why did Jason M. Lemkin Change his Point of View on The Value of a COO for Earlier Stage Startups?

SaaStr

I try to work with (and invest in) CEOs that are better than me. I felt part of your core job as CEO was to assemble a management team, not complain about how you couldn’t get it all done. I felt part of your core job as CEO was to assemble a management team, not complain about how you couldn’t get it all done.

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What Order Should You Hire Your Management Team In?

SaaStr

IME, rough order to make hires in: VPM: $0.2m Enough to invest, but not enough to go crazy with. He asked which to hire first. If you have a few nickels in the bank, and you somehow find a great VP a half stage or even full stage early, just hire her. Hiring is so hard as it is. Make the hire now.

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The Top 10 Reasons to Attend 2025 SaaStr Annual, May 13-15 in SF Bay!!

SaaStr

Including: CEO Snowflake CEO HubSpot CEO DropBox CEO Descript CEO Clio CEO Flock Safety CEO Own CRO ServiceTitan CMO Databricks CMO Infinite Reality CTO Rubrik CCO Canva CCO Bill CCO GitHub VP AI Wiz CEO Calendly and 100s more!! In addition, this year Mayfield is sponsoring our VC AI Pitch Stage and will invest from $500k-$5m in the winner!

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Top 10 GTM Mistakes Founders Make Again … and Again with SaaStr’s Jason Lemkin 

SaaStr

They hire a VP of Sales who doesn’t want to sell or learn the product. You also don’t want to hire a VP of Sales who won’t carry a bag. If you joined a startup at $2M and wanted to get to $6M with reps doing $400k, that VP of Sales would need to hire ten reps. 90% of the time, sales falls when a founder steps out of it.

CTO Hire 211
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10 Things That Would Have Helped Me Go From $1m to $10m Faster with Less Stress

SaaStr

These are all full-time jobs by $1m ARR. Fixing it yourself becomes the biggest time sink and excuse for not hiring there is. You end up spending all your time backfilling roles you should have hired. And even worse, you often sort of give up trying to make the hire. Less and you under-invest.

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30+ Tough Learnings from Losing a Top Customer

SaaStr

You have to be careful to pair that with someone strong to manage the relationship, that has more time and that also can be trusted. As a founder, you’ll just run out of time to properly manage key customers and partners yourself. We all underresource customer success vs. sales. But it’s stressful.

CTO Hire 328
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Scaling a Product-Led Growth Model with 1Password, Apollo.io, Sentry, and Lightspeed (Pod 634 + Video)

SaaStr

Lightspeed Partner, Anoushka Vaswani, is joined by Raj Sarkar, CMO at 1Password, Kim Walsh, SVP, Sales, Partnerships and Customer Success at Apollo.io, and Chris De Vylder, CRO at Sentry, to pass along key lessons from their growth journey. To do that, define what success means for you and your customers.

Scale 244