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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 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. Or couldn’t stand your CTO. I still believe a CEO should “do it all” in terms of building a decent management team first before hiring a COO. Hiring a strong COO between Management Team 1.0

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June 30, 2025: The Date Where If Your Team Hasn’t Rolled Out Truly Great AI Into Production Yet… It’s Time to Reboot the Team

SaaStr

If your engineering team, your product team, or your leadership team hasn’t shipped meaningful AI capabilities into production by now, that have led to a material increase in revenue — you don’t have a strategy problem. That requires leadership that understands both the technology possibilities and the market implications.

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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!! Investor Connections and Funding Opportunities — And $5m AI VC Pitch Stage!!

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The Top 10 SaaStr Learnings from Mary Meeker’s Latest Report on AI

SaaStr

China Is Playing a Different Game Entirely The Models Youve Barely Heard Of: DeepSeek R1: 93% performance of OpenAI’s o3-mini at fraction of training cost Alibaba Qwen 2.5-Max: China views AI supremacy as essential to geopolitical leadership. AI use will be part of what we evaluate in performance reviews.

AI Search 264
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GTM 134: When to Hire Your First Sales Reps (And How to Get It Right) with Joe DiMento

Sales Hacker

Discussed in this Episode: When to hire your first account executives Key traits to look for in early sales hires Structuring compensation for first sales reps Should you ‘hire the buyer’ to be your sales rep? 31:55 Hiring for grit, curiosity & determination. What does Joe look like at that time?

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What Order Should You Hire Your Management Team In?

SaaStr

IME, rough order to make hires in: VPM: $0.2m 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. ARR VPS: $1-$1.5m More here: [link].

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Leadership Learnings: 5 Things I Wish I Could Have Told My 2013 Self With Advisor and Former CTO of Heap Dan Robinson (Pod 663 + Video)

SaaStr

Dan Robinson, current Advisor and former CTO at Heap , shares five essential learnings from nearly a decade of building a SaaS business. What Your Job Is (And What It Isn’t) Your Job is to Make the Company Win A CTO may imagine their primary job is to provide technical expertise, lead engineers, and help build the product.

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