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The Official SaaStr Podcast: SaaS | Founders | Investors

The Official SaaStr Podcast is the latest and greatest from the world of SaaStr, interviewing the most prominent operators and investors to discover their tips, tactics and strategies to attain success in the fiercely competitive world of SaaS. On the side of the operators, we center around getting from $0 to $100m ARR faster, what it takes to scale successfully and what are the core elements of hiring. As for the investors, we learn what metrics they hone in on when examining SaaS business, what type of metrics excites them and what they look for in SaaS founders.
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The Official SaaStr Podcast: SaaS | Founders | Investors
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Now displaying: August, 2025
Aug 27, 2025

SaaStr 817: What Happens When AI Kills Your SaaS Growth? Live Q&A with SaaStr CEO and Founder Jason Lemkin

In this Q&A session from SaaStr Annual, Jason Lemkin delivers hard truths about how AI is reshaping the entire SaaS landscape. No sugarcoating, no feel-good platitudes - just the brutal reality of what's happening to B2B companies right now.

What You'll Learn:

  • Why 80% of B2B investors now only do AI deals (and what that means for traditional SaaS)
  • The real reason $100M revenue companies are suddenly hitting growth walls
  • Why VCs have shifted from seeking billion-dollar to trillion-dollar outcomes
  • How the "triple-triple-double-double" growth model died in 18 months
  • Why you need to go multi-product by $10M revenue (not $100M)
  • The downward death spiral killing SaaS companies that aren't adapting
  • Specific tactics for surviving when your go-to-market playbook stops working

Key Moments:

  • A founder admits he's "terrified" of AI - Jason's response will surprise you
  • Why vertical SaaS is becoming the only "safe haven"
  • The harsh math on fundraising when you're not AI-first
  • How brand marketing is changing as search moves from Google to ChatGPT
  • Why working "twice as hard and four times smarter" isn't optional anymore

Raw Founder Questions Answered:

  • "How do I fundraise when I'm not AI-first?"
  • "Is triple-double-double still attractive to investors?"
  • "Should my sales team experiment with AI?"
  • "How many resources should we devote to becoming AI-first?"

This isn't your typical conference recap. It's 90 minutes of unvarnished insights from founders in the trenches, dealing with the AI disruption in real-time. Jason doesn't hold back on what's working, what's broken, and what you need to do differently starting tomorrow.

Perfect for: SaaS founders, revenue leaders, and anyone trying to navigate the AI transformation of B2B software.

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Hey everybody, SaaStr AI's next stop takes us to London on December 2nd and 3rd!

 

It's Christmas with SaaStr and 2,000 of the best SaaS and AI leaders. 

 

The biggest names will be there. The best networking. 

 

Early adopter tickets are selling faster than we expected. So don't wait. With only 5 months until the event, we expect this year's SaaStr London event to sell out to capacity. 

 

Use my code jason20pod for exclusive savings. Get your tickets now at podcast.saastrlondon.com or use code jason20pod at checkout.

 

SaaStr AI London – where SaaS Meets AI in London. See you there.

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Hey everybody, SaaStr Annual will be back in May of 2026. 

The world's largest SaaS + AI gathering for executives. Just this May we hosted: 10,000 attendees with 68% VP-level and above, 36% CEOs and founders and a growing 25% were 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. Use my code JASON100 for exclusive savings. Get your tickets at podcast.saastrannual.com or use code JASON100 at checkout. 

SaaStr Annual 2026. We'll see you there. 

 
 
Aug 20, 2025

Join us as Jason Lemkin, CEO, and Founder of SaaStr, sits down with Tope Awotona, CEO, and founder of Calendly for an insightful AMA session. They discuss Calendly's journey, their success in the Product-Led Growth (PLG) domain, and how it balances self-serve with enterprise sales strategies. Tope shares candid lessons learned from growing Calendly, from managing customer acquisition costs to aligning product development with customer needs. The conversation also delves into how Calendly plans to integrate AI to enhance user productivity and manage meetings more efficiently. This episode is packed with valuable insights for founders, CEOs, and anyone interested in SaaS growth strategies.

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Hey everybody, SaaStr Annual will be back in May of 2026. 

The world's largest SaaS + AI gathering for executives. Just this May we hosted: 10,000 attendees with 68% VP-level and above, 36% CEOs and founders and a growing 25% were 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. Use my code JASON100 for exclusive savings. Get your tickets at podcast.saastrannual.com or use code JASON100 at checkout. 

SaaStr Annual 2026. We'll see you there

Aug 13, 2025

SaaStr 815: Redpoint Ventures Playbook: How Top VCs Are Really Investing in AI with Jacob Effron, Managing Director of Redpoint Ventures 

Jacob Effron, Managing Director at RedPoint, discusses the state of AI investing and the rapid advancements in AI technology. He highlights the significant decrease in model costs, increased AI capabilities in applications like coding, voice models, and customer support, and the rapid scaling of AI startups. Jacob also talks about how venture capital strategies have shifted, with a focus on AI-driven end-use cases and quality. He outlines a three-part investment framework focused on identifying effective AI applications and the potential for future expansion. Effron shares insights on successful AI companies like Abridge and Lara, emphasizing their high-quality products and rapid market adaptation. He concludes by noting the importance of brand building, velocity in product development, and the evolving landscape of AI investments.

00:00 Introduction and Speaker Background
00:25 Current Trends in AI and Model Costs
01:30 Implications for AI Application Companies
05:06 Challenges in the AI Investment Landscape
09:07 Effective AI Application Companies
10:59 Investment Framework for AI Companies
15:14 Case Studies: Abridge and Lara
21:38 Key Learnings and Final Thoughts
23:38 Q&A Session
 
 
Aug 6, 2025

SaaStr 814: How to Build Top-Performing Sales Orgs with OpenAI's GTM Leader Maggie Hott

Join Maggie Hott, GTM Leader at OpenAI, as she shares her extensive experience in building top-performing sales organizations at SaaStr. With a remarkable career history at Eventbrite, Slack, Webflow, and OpenAI, Maggie distills 15 years of insights into a tactical playbook for building and scaling sales teams. Learn key principles for hiring the right candidates, fostering thriving teams, maintaining customer obsession, and driving sustainable growth. Discover common pitfalls to avoid, the importance of storytelling, and how to align your teams for maximum impact. Whether you're a startup founder or a seasoned leader, these practical lessons will help you scale your sales team effectively.
 
 

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Hey everybody, SaaStr AI's next stop takes us to London on December 2nd and 3rd!

 

It's Christmas with SaaStr and 2,000 of the best SaaS and AI leaders. 

 

The biggest names will be there. The best networking. 

 

Early adopter tickets are selling faster than we expected. So don't wait. With only 5 months until the event, we expect this year's SaaStr London event to sell out to capacity. 

 

Use my code jason20pod for exclusive savings. Get your tickets now at podcast.saastrlondon.com or use code jason20pod at checkout.

 

SaaStr AI London – where SaaS Meets AI in London. See you there.

 

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This episode of the SaaStr podcast is sponsored by: get.tech

The best .coms are taken or overpriced. So you settle on a workaround domain for your website.

Don't compromise. Get a clean, sharp .tech domain that instantly says: this is a tech startup.

Grab yours at get.tech/saastr or via domain registrars like GoDaddy.

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