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Dear SaaStr: We Can Sell to a New Vertical. Should We?
Aug 31, 2025
Dear SaaStr: We Can Sell to a New Vertical. Should We? Getting ahead of expanding into new verticals can be a huge win. You really want to get there, and to a second product, before you exhaust your TAM in your existing markets and product. But of course it’s not...
One Way Even Great Sales Execs Fail: Not Spending Enough Time IRL With Their Team
Aug 30, 2025
I caught up with two sales leaders recently — both seasoned, both with strong track records, both ethical operators. And both had just washed out of their latest sales roles in under 6 months. That seemed... odd. So I dug deeper. What I found was a common thread that...
How We Built ChatGPT Enterprise’s Sales Team from Absolute Zero: The Complete Playbook with Maggie Holt, Head of GTM
Aug 30, 2025
How We Built ChatGPT Enterprise's Sales Team from Absolute Zero: The Complete Playbook with Maggie Hott, GTM Leadership at OpenAI About Maggie: Maggie Hott has spent 15 years building go-to-market teams at four unicorns that collectively represent over $50B in market...
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Blog Posts, Q&A
Dear SaaStr: We Can Sell to a New Vertical. Should We?
By Jason Lemkin | August 31, 2025
Dear SaaStr: We Can Sell to a New Vertical. Should We? Getting ahead of expanding into new verticals can be a huge win. You really want to get there, and to a second product, before you exhaust your TAM in your existing markets and product. But of course it’s not without risk. The first key…
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Blog Posts
One Way Even Great Sales Execs Fail: Not Spending Enough Time IRL With Their Team
By Jason Lemkin | August 30, 2025
I caught up with two sales leaders recently — both seasoned, both with strong track records, both ethical operators. And both had just washed out of their latest sales roles in under 6 months. That seemed… odd. So I dug deeper. What I found was a common thread that might surprise you: Neither had really…
Continue Reading
Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
How We Built ChatGPT Enterprise’s Sales Team from Absolute Zero: The Complete Playbook with Maggie Holt, Head of GTM
By Jason Lemkin | August 30, 2025
How We Built ChatGPT Enterprise’s Sales Team from Absolute Zero: The Complete Playbook with Maggie Hott, GTM Leadership at OpenAI About Maggie: Maggie Hott has spent 15 years building go-to-market teams at four unicorns that collectively represent over $50B in market value. She started as the 2nd SDR at Eventbrite, became the first sales hire…
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