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Lenny Rachitsky: evaluation

9 Nov 2025 Lenny's Podcast "Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel

“I think about linear, which started very startup-ey and my take is they did that because changing the way you work is really hard and their bet was like, "Let's start with companies and grow with them and over time that becomes the default.”

— Lenny Rachitsky

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Speaker
Lenny Rachitsky
Attribution
Verified speaker
Claim type
evaluation
Recorded
9 Nov 2025
Publisher
Lenny's Podcast

Transcript context

…I think it's about, and I read this somewhere and I wholeheartedly agree with it because I've seen it live. I think it's about what game does the founder best understand? Are they an incredible marketer and have some competitive edge for how they can win a massive audience? I would say go SMB and marketing led or are they a bit more really understand how large corporations work and really excited to deliver on $100,000 plus type of opportunities or the value that they are building for is way more relatable to an enterprise versus a small business. That is really interesting. I've never heard of it described that way. I think about linear, which started very startup-ey and my take is they did that because changing the way you work is really hard and their bet was like, "Let's start with companies and grow with them and over time that becomes the default. " Any reaction to that? I think that it sounds like that that's a great way to work because that's a technical tool, so that you need the right, also need to have the right infrastructure to sell. I think Slack, look, Slack and Microsoft Teams are still battling it out at the enterprise. I think it's also how you plug in and how you integrate and do they even have the right systems to support you? The thing with open AI is they didn't have to connect to anything.…

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