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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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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. Sessions typically focus on real metrics, strategies, and lessons learned, not theoretical concepts.

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Extreme Product Design: Building Things People Actually Use with Stripe CTO David Singleton (Pod 636 + Video)

SaaStr

Many companies believe excellent product design comes from hiring the best engineers and signing up for the latest software instead of building from the users’ perspectives. Stripe’s CTO, David Singleton, shares how they use a system of feedback, iteration, and fast shipping to create products that meet users’ expectations.

CTO Hire 292
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Using Generative AI to Drive Corporate Impact

TechEmpower SaaS

The shift towards AI-driven ad technologies enables brands to set and achieve highly specific engagement KPIs, moving away from generic strategies to more personalized, data-driven approaches that resonate with their target audience. This not only speeds up hiring but also lowers the costs associated with lengthy recruitment cycles.

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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.

CTO Coach 242
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Top SaaStr Content for the Week: Dave Kellogg, PayFit and Insider CEOs, Notion COO, Salesforce CMO and More!

SaaStr

An updated classic SaaStr guide on how to know if that new VP you worked so hard to find, recruit and get on board … is really going to make it. 4 Signs You Might Have a “Bad” CTO — Or At Least, One That Isn’t Going to Make It. 7 Secrets to a Successful SMB GTM Strategy with PayFit and Accel.

New CTO 300
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Why Some VC Investments Work Out, and Some Don’t. What I’ve Learned.

SaaStr

Investments I've made that didn't work out: – Momentum investment – CEO a bit of bulls**t artist – CEO good at sales but weak product team / CTO. This has been a total negative strategy for me. There are ways to make this strategy work. CEO good at sales, but CTO not that great. Really hard.