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

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

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.

In this session, CRO of ServiceTitan, Ross Biestman, and Chemistry's Managing Partner and Co-Founder, Kristina Shen, discuss ServiceTitan's founding principles and growth from a small company to a $11 billion vertical SaaS leader. Together they cover ServiceTitan’s mission-driven approach, and its successful adoption of AI for operational efficiency. Ross shares personal anecdotes about customer interactions and pivotal moments leading to ServiceTitan’s massive success. The episode underscores the importance of on-site customer interactions and the role of AI and disciplined expansion in their growth strategy.

------------------

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.

------------------

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.

------------------

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 812: What’s Working Now: AI’s Real Impact on Sales with SaaStr's CEO and Co-Founder, and SVP & GM 

Join Jason Lemkin, CEO and Founder of SaaStr, and Amelia Lerutte, SVP and GM of SaaStr as they dive deep into the practical applications, results, and learnings from integrating AI into sales workflows.

This session covers the initial struggles, data preparation, and continuous optimization required to achieve high-quality outputs with AI. They share specific examples of what's working, the importance of human oversight, and the benefits of combining AI with human expertise. Whether you're initiating outbound sales or reactivating lapsed accounts, learn how SaaStr successfully increased response rates and closed deals using AI-driven strategies.

------------------

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.

------------------

 

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.

------------------

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

SaaStr 811: Marketing in the Age of AI with Wiz's CMO Raaz Herzberg

Join us for an insightful discussion with Raaz Herzberg, the Chief Marketing Officer of Wiz, as she dives into her unconventional journey from engineering to leading Wiz's marketing strategy.

In this episode, Raaz shares her unique perspectives on how a lack of traditional marketing background shaped her approach, focusing on building brand awareness and solving customer pain points. Learn about the innovative tactics she's employed to stand out in the cybersecurity market, the importance of hiring curious and driven individuals, and how AI is transforming the marketing landscape. Whether you're in marketing, sales, or a founder, Roz offers valuable advice on making impactful hires and driving exponential growth.

------------------

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.

------------------

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

SaaStr 810: AI and the Bottom Line, How Canva Turns Freemium into Conversions with Canva's CCO Rob Giglio

Join John Gleason, founder and managing partner at Success Venture Partners, as he interviews Rob Giglio, Chief Customer Officer at Canva. Rob shares his extensive experience leading customer success, sales, and go-to-market functions at top companies like HubSpot, DocuSign, and Adobe. In this episode, Rob delves into his strategic approach to scaling Canva's enterprise business while maintaining the company’s unique customer-centric culture. He also discusses the integration of AI to enhance customer experiences and how value-driven customer journeys underpin Canva’s growth. Perfect for aspiring CCOs and anyone interested in the intersection of customer success and sales.   00:00 Introduction and Guest Welcome 00:29 Rob's Role and Responsibilities at Canva 03:11 Career Journey and Mentorship 07:17 Building Enterprise at Canva 14:20 Customer-Centric Approach 21:42 AI Integration at Canva 24:36 Conclusion and Final Thoughts     ----

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.

----

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.

SaaStr 809: Why Enterprise AI Adoption Is Moving 5-10X Faster Than Cloud with Box's CEO and Co-Founder, IBM's VP for AI and SaaStr's CEO and Founder

This conversation between Aaron Levie, CEO & Co-Founder of Box, Raj Datta, Global Vice President for Software and A.I. Partnerships at IBM and Jason Lemkin, CEO and Founder of SaaStr, covers the evolution from chat interfaces to digital labor models, the integration of AI to automate complex tasks, and the emergence of new paradigms for businesses deploying AI agents. Key topics include the distinction between AI agents and assistants, the development of proprietary data models, and the rapid pace of AI adoption. With real-world examples from companies like IBM and Box, this session offers insights into how AI is reshaping software ecosystems, enhancing enterprise capabilities, and potentially redefining market moats.

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This episode of the SaaStr podcast is sponsored by: Attention.com

 

Tired of listening to hours of sales calls? Recording is yesterday’s game. Attention.com unleashes an army of AI sales agents that auto-update your CRM, build custom sales decks, spot cross-sell signals, and score calls before your coffee’s cold. Teams like BambooHR and Scale AI already automate their Sales and RevOps using customer conversations. Step into the future at attention.com/saastr

 

------------------

 

Hey everyone, we just hosted 10,000 of you at the SaaStr Annual in the SF Bay Area, and now get ready, because SaaStr AI is heading to London!

On December 2nd and 3rd, we’re bringing SaaStr AI to the heart of Europe. This is your chance to connect with 2,500+ SaaS and AI executives, founders, and investors, all sharing the secrets to scaling in the age of AI.

 

Whether you’re a founder, a revenue leader, or an investor, SaaStr AI in London is where the future of SaaS meets the power of AI.

And we just announced tickets and sponsorships, so don’t wait! Head to SaaStrLondon.com to grab yours and join us this December in London.

SaaStr AI in London —where SaaS meets AI, and the next wave of innovation begins. See you there!

SaaStr 808: AI and Cybersecurity: Scaling Rubrik to a Billion Dollar Enterprise with Rubrik's Co-Founder and CTO

In this episode, Kit Colbert, former CTO of VMware and Platform CTO at Invisible, sits down with Arvind  Nithrakashyap, Co-founder and CTO of Rubrik, to discuss the company's journey and innovations over the last 11 years.    Arvind  shares insights into Rubrik's platform for cyber resilience, their approach to scaling with multiple product pillars, and their unique use of hackathons to spark innovation. The conversation also delves into customer satisfaction strategies, the implementation of AI in both their products and internal processes, and how they measure the ROI of AI initiatives. With highlights of Rubrik's 39% year-over-year growth, a Net Promoter Score (NPS) of 80, and the launch of their AI product Ana, this episode offers valuable takeaways for businesses looking to scale and innovate.  

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This episode of the SaaStr podcast is sponsored by: Attio

This episode is brought to you by Attio — the AI-native CRM. Connect your email, and Attio instantly builds a powerful CRM - with every company, contact and interaction you've ever had. Get 15% off your first year at https://attio.com/saastr

 

------------------

This episode of the SaaStr podcast is sponsored by: Attention.com

Tired of listening to hours of sales calls? Recording is yesterday’s game. Attention.com unleashes an army of AI sales agents that auto-update your CRM, build custom sales decks, spot cross-sell signals, and score calls before your coffee’s cold. Teams like BambooHR and Scale AI already automate their Sales and RevOps using customer conversations. Step into the future at attention.com/saastr

------------------

Hey everyone, we just hosted 10,000 of you at the SaaStr Annual in the SF Bay Area, and now get ready, because SaaStr AI is heading to London!

On December 2nd and 3rd, we’re bringing SaaStr AI to the heart of Europe. This is your chance to connect with 2,500+ SaaS and AI executives, founders, and investors, all sharing the secrets to scaling in the age of AI.

Whether you’re a founder, a revenue leader, or an investor, SaaStr AI in London is where the future of SaaS meets the power of AI.

And we just announced tickets and sponsorships, so don’t wait! Head to SaaStrLondon.com to grab yours and join us this December in London.

SaaStr AI in London —where SaaS meets AI, and the next wave of innovation begins. See you there!

SaaStr 807: Snowflake's CEO on the AI Data Cloud, Partner Strategy, and What’s Next

Join Sridhar Ramaswamy, CEO of Snowflake, and Jeremy Burton, CEO of Observe, in a comprehensive discussion led by SaaStr CEO & Founder, Jason Lemkin. Discover the inner workings of Snowflake's Board, the dynamics of strategic partnerships, and the evolving role of AI in data management. Learn how Snowflake aims to be the AI Data Cloud and how Observe integrates with Snowflake to provide scalable analytics. With detailed insights into the partnership strategies, future technological trends, and success stories, this conversation offers a blueprint for leveraging AI and data to drive business value. Don't miss out on the valuable lessons and future predictions shared by these industry leaders.

-----------------

This episode of the SaaStr podcast is sponsored by: Attio

This episode is brought to you by Attio — the AI-native CRM. Connect your email, and Attio instantly builds a powerful CRM - with every company, contact and interaction you've ever had. Get 15% off your first year at https://attio.com/saastr 

------------------

This episode of the SaaStr podcast is sponsored by: Attention.com

Tired of listening to hours of sales calls? Recording is yesterday’s game. Attention.com unleashes an army of AI sales agents that auto-update your CRM, build custom sales decks, spot cross-sell signals, and score calls before your coffee’s cold. Teams like BambooHR and Scale AI already automate their Sales and RevOps using customer conversations. Step into the future at attention.com/saastr

------------------

Hey everyone, we just hosted 10,000 of you at the SaaStr Annual in the SF Bay Area, and now get ready, because SaaStr AI is heading to London!

On December 2nd and 3rd, we’re bringing SaaStr AI to the heart of Europe. This is your chance to connect with 2,500+ SaaS and AI executives, founders, and investors, all sharing the secrets to scaling in the age of AI.

Whether you’re a founder, a revenue leader, or an investor, SaaStr AI in London is where the future of SaaS meets the power of AI.

And we just announced tickets and sponsorships, so don’t wait! Head to SaaStrLondon.com to grab yours and join us this December in London.

SaaStr AI in London —where SaaS meets AI, and the next wave of innovation begins. See you there!