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Why It’s Easier for Second-Time Founders to Raise Venture Capital. Even With Nothing Even Built Yet.

SaaStr

Dear SaaStr: Why Is It So Easy For Entrepreneurs With Previous Success to Raise Funds From VCs for Their New Venture Despite Not Having Domain Expertise? As Dharmesh Shah co-founder and CTO notes in the SaaStr Annual deep dive below, the second time … they just really wanted to go big. It doesnt necessarily work better.

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SaaStr Annual + SaaStr AI Summit 2025: Meet The Best of The Best in Cloud, B2B and AI! May 13-15 in SF Bay!!

SaaStr

The ultimate gathering of SaaS and AI leadership is about to happen in San Francisco. It’s days away now! SaaStr Annual + SaaStr AI Summit 2025! We’re bringing together the true founders, revenue leaders and product visionaries that are actually driving the next wave of AI first software. Not talking heads. Not theorists.

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Calm’s Will Larson on how to build a technical leadership career

Intercom, Inc.

For those who don’t know him, Will has over 10 years of experience in the likes of Yahoo, Digg, Uber, and Stripe, and he’s currently the CTO of Calm , the mindfulness app that helps millions of people to lower their stress levels and sleep better. Solvers tend to be reactive to what leadership is really worried about. How do we fix it?”

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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. Workflow transformation that creates new value. Give your new AI team real authority.

AI Search 170
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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!! Competitive Intelligence and Market Insights and New!!

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Technical Review: A Trusted Look Under the Hood

TechEmpower SaaS

The explanation from software leadership is often unsatisfying or unclear. Common Signs You Need a Technical Review We’ve already mentioned the most common signs that you might need a technical review: Slow or late delivery: “I’ve authorized two new developers, and we’re still behind.” What does a business leader do in this situation?

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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. Focus on retaining your engineers from day one. More like this at 2022 SaaStr Annual, Sep 13-15 in SF Bay Area!!

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