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AI, Sales + GTM in 2025/2026: This Changes Everything with Jason Lemkin and Owner CRO Kyle Norton

SaaStr

At SaaStr + AI Summit 2025, Jason Lemkin and Kyle Norton CRO of $1B+ vertical SaaS leader Owner (where Jason is on the board) did a deep dive on AI in Sales today. By the end of this quarter, team members who aren’t genuinely AI-curious should be let go. The 50/50 Team Is Coming Fast. And where it will be very soon.

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What Happens When You Hire the Wrong VP

SaaStr

You know how everyone says you'll never look and wish you'd kept a bad VP as long as you did? That when you make a mis-hire, you'll always look back and say you should have made a change 3-4 month earlier? When to hire them. Some classics here: How My VP, Sales Doubled Our Sales in 90 Days.

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4 Things Most Founders Get Wrong About Marketing with Dave Kellogg

SaaStr

The 4 Things Most Founders Get Wrong About Marketing: “We’re a product company, not a marketing company” – The hard truth is that 9 out of 10 B2B companies spend more on sales and marketing than R&D. Better to hire for your specific needs and stage. These “five-five” CMOs barely exist.

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The Compound Startup Advantage: Why The CEO of Rippling Believes Focus Is Overrated

SaaStr

Conrad personally runs payroll for Rippling’s 2,000 employees across a dozen countries as a “part-time job,” while UK companies with even small teams often spend 5-6 days monthly just managing payroll. This structure enables a seamless experience that starts when a company hires someone.

Startup 163
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CEOs of Zapier, Walkme and Dialpad: How to Build Your First Management Team (Video + Transcript)

SaaStr

So let’s take a look back to a deep dive with the CEOs on what they learned building their first senior teams: ———-. As a founder/CEO, building your first management team is something that you often lose sleep over. Which role should you hire for first? And for good reason. One thing is the timing.

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The Secrets to Building a World-Class, $2.3 Billion Inside Sales Team (Video + Transcript)

SaaStr

Hear from Duo Security’s VP of Inside Sales America on how to build a $2.3B sales team. Jennifer Lawrence | VP, Inside Sales @ Duo Security. Today I’m going to start by telling you a little bit about me, a little bit about Duo, and then the secrets to building a killer inside sales org. Good afternoon.

Scale 284
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The Best of SaaS at YCombinator: A Deep Dive with the CEOs of Gusto, Amplitude and Plangrid (Video + Transcript)

SaaStr

For us, it’s about fixing this problem, serving the customer well, so a very service driven mindset, which I gave a talk on a few days ago here, has been a big part of Gusto and affected our hiring from the early days. The second is pulling more around values, and how we approached team building. Get tickets here. TRANSCRIPT.