SaaStr Podcasts
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. How do you get from $0 to $100m ARR faster? What does it take to scale successfully?
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What’s New at Box and the Future of AI and SaaS in 2024 with Box CEO and Co-Founder Aaron Levie
In our ‘What’s New’ series, SaaStr CEO and Founder Jason Lemkin sits down with the top CEOs from leading SaaS companies to discuss What’s New and what’s top of mind. In this episode, Jason sits down with Aaron Levie, CEO and Co-Founder of Box, and also a SaaStr-fan fave from speaking at various SaaStr events in-person and digitally. Together they discuss: How to go long as a CEO and Founder in SaaS, Overhauling operating margins at Box to a top-tier 25%, Macro issues on the horizon for 2024, Incorporating AI and LLMs into the product and What’s new at Box.


The Top 10 Mistakes People Make When Hiring a VP of Sales with SaaStr CEO and Founder Jason Lemkin
Hiring a VP of Sales isn’t new, but the conversations have evolved as the world has. SaaStr CEO Jason Lemkin shares the top 10 mistakes he sees.


CRO Confidential: The Hangover’s Over: 5 Ways to Get Your SaaS Revenue Back On Track with Gong’s SVP Sales and Founders Fund
After a period in 2021 known as “The Party”, where salespeople earned more while working less, businesses are shifting focus from measuring effort to emphasizing revenue generation. As the market bounces back, learn 5 ways to get back to hitting revenue targets with Jameson Yung, SVP of Sales at Gong, and Sam Blond, Partner at Founders Fund and previous CRO at Brex.


Who Will Win the GTM AI Race — Startups vs. Incumbents? With Stage 2 Capital Co-founder and Managing Director Mark Roberge
As AI continues to reshape the way businesses operate, it has become a critical differentiator in gaining a competitive edge. Stage 2 Capital Co-founder and Managing Director Mark Roberge dissects the advantages and challenges faced by both startups and incumbents in leveraging AI for Go-to-Market strategies. Uncover the unique capabilities that startups bring to the table and how they disrupt established players with their agility, innovation, and ability to adapt to changing market dynamics.


Hitting Hypergrowth: How To Take Your SaaS Company from $25M to $100M and Beyond with Amplitude’s CEO, Spenser Skates
Discover four critical lessons for maintaining hypergrowth on your journey from nothing to $100M and beyond with the CEO and co-founder of Amplitude.


The 5 Ways AI Will Transform Creativity with Adobe CSO & EVP Scott Belsky (Video + Podcast)
Discover the five ways of change impacting the creative industry with the rise and power of AI. Adobe CSO & EVP Scott Belsky shares how the creative industry will evolve, and it doesn’t involve replacing creatives with AI.


Nick Mehta, CEO Gainsight: My Top 10 Failures as a SaaS CEO & What I’ve Learned (Video + Podcast)
In this session Nick Mehta will share ten significant mistakes he made during his career, and how these failures shaped his journey as CEO of Gainsight. Mehta will impart valuable lessons on resilience and growth, offering attendees actionable takeaways for their own entrepreneurial ventures. This talk is a must-watch for anyone seeking to learn from real-life experiences and turn failures into opportunities for success in the software-as-a-service (SaaS) world.


CRO Confidential: The Proven Customer Acquisition Strategies Behind Toast’s Explosive Growth with Founders Fund Partner Sam Blond and CRO of Toast Jonathan Vassil
In this new episode of CRO Confidential, we take a look at the proven customer acquisition strategies behind Toast’s explosive growth to over $1.1B ARR. Hosted by Founders Fund Partner Sam Blond, this episode features CRO of Toast Jonathan Vassil, who walks us through Toast’s go-to-market and customer acquisition strategies.


How to Navigate Strategic Change for Growth with SaaStr CEO and Founder Jason Lemkin (Video + Podcast)
Jason re-takes the stage in Part 2 of the series to answer questions about the right time is to invest in a new product line, building vertical vs. horizontal, multiples in 2024, and much more.


What SaaStr CEO and Founder Jason Lemkin Really Thinks About AI, Sales & Lead Gen In 2024
SaaStr CEO and Founder Jason Lemkin covers everything you need to know about hiring, AI, and lead generation in SaaS going into 2024.


The Chat GPT Growth Story: How AI is Changing the Way We Work with OpenAI’s Head of Sales, Aliisa Rosenthal
Discover how AI is changing how we work and how OpenAI has opened the door for innovation on a rapid scale with OpenAI’s Head of Sales, Aliisa Rosenthal.


How to Close More Deals with Less Budget with Datadog CMO Alex Rosemblat
Learn how to close more SaaS deals with less budget and enable your sellers for maximum conversion rates with Datadog’s CMO.


Lessons on Scaling Customer Success from $1M to $300M in ARR with Success Venture Partners
Learn what it takes to scale Customer Success at every stage of growth — from $1M to $300M+ in ARR — with founder and Managing Partner at Success Venture Partners and former VP of Customer Success at Motive.


The Key To Unlocking Profitability and Growth in SaaS with Expensify’s COO Anu Muralidharan
How do you build a successful, high-growth company that is also profitable? Expensify’s COO, Anu Muralidharan, debunks the fallacy that profitability comes at the expense of growth.
Popular Q&A
Dear SaaStr: Can an Entrepreneur Back Out of a Signed Term Sheet Without Damaging Their Reputation?
Dear SaaStr: Can an entrepreneur back out of a signed term sheet without damaging their reputation? In my experience — Yes, probably. As a founder, you can back out of a term sheet if something is off, or even if you just get another offer you prefer. There is a lot...
Why You’re Unfundable in 2023: The Cold, Hard Truths About SaaS AMA Part 2 with SaaStr CEO and Founder Jason Lemkin
Jason Lemkin, CEO and Founder of SaaStr, recently answered our audience’s most pressing questions about the present and future of startups. Here is part 2 of the cold truth about SaaS in 2023.
The Cold, Hard Truths About SaaS In 2023: Part 1 AMA with SaaStr CEO and Founder Jason Lemkin
Jason Lemkin, CEO and Founder of SaaStr, recently answered our audience’s most pressing questions about the present and future of startups. Here is part 1 of the cold truth about SaaS in 2023.
7+ Tips On How To Build Your First Sales Team. When You Have Zero Experience Building One.
Q: How do you structure a sales team when you’ve got zero experience doing sales? Well, first go get some experience with sales. 🙂 At least, close the first 10 customers yourself. If you don’t, you’ll never have any idea how to do it. And the odds your first rep...
15+ Due Diligence Questions You Really Should Be Asking Every VC You Meet
Dear SaaStr: What is the proper way to do due diligence on a VC firm? Here are the things, IMHO and IME, that are most important. First, if you want to do it right, you should diligence both (1) the firm and (2) the individual partner leading the deal. Importantly,...
The 3 Types of Day 1 Pricing: Low End of Normal. Identical. And Anchor High.
Q: As an entrepreneur starting out, is it better to overprice your product or underprice it? I remember years ago I was at an event with the CEO of a SaaS leader. And I asked him how he came up with their freemium pricing model. A data science team? A/B Testing? "No....
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