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

SaaStr

Our recent SaaStr Summit: Bridging the Gap was the first time I’ve had a chance to be a participant at a SaaStr event in a long, long time. He joined StubHub as CTO, but didn’t get nearly as much equity as the other CTO — because he “wasn’t committed enough.” I learned a lot! ??

CTO Hire 355
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The Top 10 Reasons to Attend 2025 SaaStr Annual, May 13-15 in SF Bay!!

SaaStr

The event is strategically designed to facilitate 1000s of meaningful connections through 1000+ on-site “Who Do You Want To Meet” dedicated 1-on-1s for B2B founders and execs (no service providers, sorry!) The event attracts investors ranging from seed-stage to growth equity, making it relevant regardless of your funding stage.

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The SaaS Org Chart Live with David Sacks (Podcast #491 and Video)

SaaStr

You’ll need to hire aggressively to get to the next level and continue that rapid growth. But what roles should you hire for, and what will your org chart look like at each stage? David Sacks: SaaS Background and Investments. Positions Needed: Demand Gen, Product Marketing, Sales Enablement, Events/Community.

CTO Hire 291
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80 Founders Share The Moment They Knew … When They Really Had Something

SaaStr

I should have known in fact when I spoke at an event with 4 leading tech companies … and all 4 talked about how they used Adobe Sign / EchoSign. ” — Jason Riedel, founder/CTO of Aspireship. “When on New Year’s Eve, customers kept sending us signed contracts.” 20% conversion.

CTO Hire 347
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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. Hire that person, and make sure they are someone the top customers can really trust and count on.

CTO Hire 328
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AMA at SaaStr Annual 2022 with SaaStr Founder & CEO Jason Lemkin – Part 1 (Pod 607 + Video)

SaaStr

Black Swan events. They were aware of it, but startups that I work with closely or invested in, if they got all the way to 25 million with 75% NRR, I would tell them to quit today. Your core models for sales, for marketing spend, for hiring and engineering and product. VCs can only invest in outliers. Setting goals.