SaaStr 833: AI and the Death of the 2021 Sales Playbook with SaaStr CEO and Founder Jason Lemkin

SaaStr 833: AI and the Death of the 2021 Sales Playbook with SaaStr CEO and Founder Jason Lemkin

Author: SaaStr December 17, 2025 Duration: 54:56

SaaStr 833: AI and the Death of the 2021 Sales Playbook with SaaStr CEO and Founder Jason Lemkin

Join SaaStr CEO and Founder Jason Lemkin from SaaStr London as we tackle pressing topics in AI and sales during an engaging AMA session.

From discussing the evolution of inbound vs. outbound sales to detailing the transformative impact of AI on sales roles and outbound strategies, this session covers it all.

Learn about the importance of product expertise for selling AI solutions, the rise of AI SDRs, and why knowing your top three problems is crucial for effective outbound marketing. Plus, discover insights on the rapidly improving capabilities of AI agents and their implications for competitive moats. Whether you're a sales professional, marketer, or tech enthusiast, this episode is packed with actionable insights and future trends in the AI landscape.

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This episode is Sponsored in part by HappyFox:

Imagine having AI agents for every support task — one that triages tickets, another that catches duplicates, one that spots churn risks. That'd be pretty amazing, right? HappyFox just made it real with Autopilot. These pre-built AI agents deploy in about 60 seconds and run for as low as 2 cents per successful action. All of it sits inside the HappyFox omnichannel, AI-first support stack — Chatbot, Copilot, and Autopilot working as one. Check them out at happyfox.com/saastr

 

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Hey everybody, the biggest B2B + AI event of the year will be back - SaaStr AI in the SF Bay Area, aka the SaaStr Annual, will be back in May 2026. 

With 68% VP-level and above, 36% CEOs and founders and a growing 25% AI-first professionals, this is the very best of the best S-tier attendees and decision makers that come to SaaStr each year.  

But here's the reality, folks: the longer you wait, the higher ticket prices can get. Early bird tickets are available now, but once they're gone, you'll pay hundreds more so don't wait. 

Lock in your spot today by going to podcast.saastrannual.com to get my exclusive discount SaaStr AI SF 2026. We'll see you there.


Tune into The Official SaaStr Podcast: SaaS | Founders | Investors for direct conversations with the people building and funding the software-as-a-service industry. This isn't about abstract theory; it's the practical, often hard-won wisdom from prominent founders and seasoned investors who have navigated the path themselves. Each episode digs into the specific mechanics of scaling a SaaS business, focusing on the critical journey from zero to one hundred million dollars in annual recurring revenue. You'll hear founders break down what actually worked when it came to hiring key talent, entering new markets, and managing the immense pressure of hyper-growth. From the investor side, the discussions reveal how top venture capitalists evaluate potential, what metrics truly matter beyond the pitch deck, and their perspectives on sustainable company culture. Hosted by SaaStr, this podcast serves as an ongoing masterclass for operators and entrepreneurs who prefer learning through candid stories and detailed strategies rather than generic advice. The dialogue is always grounded in the fierce realities of the competitive tech landscape, making every interview a source of actionable insights you can apply to your own challenges.
Author: Language: English Episodes: 100

The Official SaaStr Podcast: SaaS | Founders | Investors
Podcast Episodes
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