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10 Learnings From Jeff Lawson (CEO Twilio) + Byron Deeter (Bessemer Ventures): “Adapt, Plan, Deliver”

SaaStr

He joined StubHub as CTO, but didn’t get nearly as much equity as the other CTO — because he “wasn’t committed enough.” ” They had that conversation enough times to just build the first Twilio API. But at that time, fundraising was really tough. They wanted to invest in apps, not APIs.

CTO Hire 355
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“What Do You Mean They Quit?!” Don’t Give Your Engineers a Reason to Leave with Notion’s Head of Engineering: Michael Manapat, Change.org’s CTO: Elaine Zhou, and Plato’s CEO: Quang Hoang (Video)

SaaStr

Co-founder and CEO of Plato, Quong Hoang, the #1 mentoring platform for engineering leaders , helped moderate a discussion between CTO of Change.org, Elaine Zhou, and Head of Engineering at Notion, Michael Manapat, on this subject. Companies must prove they have the growth, revenue, and users to warrant serious talent.

CTO Coach 278
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The Top 10 Reasons to Attend 2025 SaaStr Annual, May 13-15 in SF Bay!!

SaaStr

200+ dedicated workshops and braindates with the best in SaaS, Cloud and AI, from intimate small sessions to 20-50 person workshops from the best Our CRO + CEO Poker Night where we bring 200 top revenue leaders together with CEOs and founders of B2B / AI companies attending Our 4th annual CMO Summit for top CMOs and the CEOs that want to meet them!

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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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What SaaStr CEO and Founder Jason Lemkin Really Thinks About AI, Sales & Lead Gen In 2024

SaaStr

For part one of this Ask Me Anything session, Jason covers everything you need to know about hiring your first VP of Sales, what he really thinks about AI, what the future of lead generation in 2024 looks like, and much more. There are no Cloud magicians, and you can’t hire a PLG magician. Let’s jump right into the questions.

Scale 290
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Doubling Down: Erica Brescia, Managing Director at Redpoint Ventures

SaaStr

What’s your most recent disclosed investment? Jason Warner , who was CTO of GitHub before and during my time as COO there (and a former partner at Redpoint!) What’s your sweet spot for investing — check size, stage, type of deal? We are currently investing out of our 9th Early Stage fund, a $650M vehicle.