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The SaaS Podcast - Building SaaS in the AI Era

The SaaS Podcast - Building SaaS in the AI Era

By: Omer Khan
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 AI is changing how SaaS gets built, priced, and used. Every week, Omer Khan interviews founders who are adapting and winning right now. With 500+ founder conversations and 150+ founders coached, The SaaS Podcast delivers the real lessons you need to build and grow your SaaS business in the AI era. No hype. No theory. Just proven strategies from founders who've done it. Join 5,000+ founders at SaaS Club. New episodes weekly. Economics Leadership Management & Leadership
Episodes
  • Enterprise Sales: How Egnyte Competed Against Box and Dropbox

    Enterprise Sales: How Egnyte Competed Against Box and Dropbox
    Feb 26 2026
    Hundreds of competitors. Billions in funding. All giving product away for free. Vineet Jain ignored the playbook. No freemium. Enterprise sales only. A hybrid cloud approach nobody believed in. In this episode, founders will learn how Egnyte grew from $0 to $300M+ while raising just $137.5M - and why charging from day one beat free. Egnyte now has 23,000 customers, 1,400 employees, and has raised no additional funding since 2018. It took 12 years to hit $100M - then just 3 more to reach $200M and 1.5 to hit $300M. This episode is brought to you by: 🌎 ThreatLocker → Book a demo 🔑 Key Lessons 🏢 Enterprise sales can outperform freemium in a crowded market: Egnyte refused free tiers while Box and Dropbox gave products away. Charging from day one built a sustainable business on just $137.5M raised. 💰 Start your enterprise sales pipeline with SEM before building a sales team: Vineet spent $6,000 on SEM in month one. That approach scaled to millions per quarter and still drives 60% of pipeline today. 🎯 Lead with compliance and security to win deals as a tiny startup: Egnyte landed a Fortune 86 customer within its first 25 deals by focusing on certifications and content governance. 📉 Use failure to build defensible differentiation: Vineet's first startup got crushed by Oracle and SAP. That taught him to build capabilities giants cannot easily replicate, like hybrid cloud. 🧠 Replace consensus with small teams of 3 for faster decisions: Critical decisions at Egnyte are owned by teams of 3 with full accountability, not committees. 🛠️ Build hybrid when the market says go cloud-only: About 30% of Egnyte customers use hybrid deployment for use cases where pure cloud fails. 🚀 Scale inside sales in low-cost cities to keep CAC low: Egnyte built offices in Spokane, Raleigh, and Salt Lake City instead of expensive tech hubs. Chapters Introduction What Egnyte does and company overview Revenue milestones and funding history Arriving in the US with $100 and no connections First startup Valdero - raised $7.5M and failed Starting Egnyte with 4 co-founders and no funding Going enterprise-only when everyone said do freemium The hybrid cloud bet Landing the first enterprise customers with $6K in SEM A Fortune 86 company visiting a 12-person startup Why employees come first, not customers Consensus is the shortest path to mediocrity AI strategy and the Egnyte Copilot launch Lightning round 💌 Get weekly 5-minute SaaS insights: https://saasclub.io/email SaaS Club Programs Join the SaaS Club founder community: https://saasclub.co/plus Build your $10K MRR SaaS: https://saasclub.io/launch Scale from 6-figures to $1M ARR Faster: https://saasclub.io/mastermind Get 1:1 async coaching from Omer: https://saasclub.io/accelerate Resources Full show notes: https://saasclub.io/471 Subscribe to the podcast: https://saasclub.io/subscribe
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    51 mins
  • Product-Market Fit: From Edtech Vitamin to $100M Painkiller

    Product-Market Fit: From Edtech Vitamin to $100M Painkiller
    Feb 19 2026
    Seven years selling a nice-to-have. Then 1,000 customers in year one. Adam Markowitz spent nearly a decade grinding in edtech before finding product-market fit at Drata. In this episode, founders will learn how to tell the difference between a vitamin and a painkiller - and why that distinction changes everything. Adam shares how experiencing a compliance pain at his first startup became the foundation for Drata, why he refused to sell until his team used their own product to get SOC 2 compliant, and how a "give before you take" approach to AWS made Drata a top 5 ISV on Marketplace in under two years. Drata has over 8,000 customers across 60 countries, more than 600 employees, and crossed $100 million in ARR before its fourth birthday. The company has raised over $300 million. This episode is brought to you by: 🌎 ThreatLocker → Book a demo 🔑 Key Lessons 🎯 Product-market fit shows in buyer urgency, not just signups: Drata signed 100 customers in 6 weeks and 1,000 in year one - a stark contrast to Adam's edtech company where the first 5 university customers took years to close. 🛠️ Dogfood your product before selling it: Drata refused to accept customers until they used their own tool to get SOC 2 compliant, giving them instant credibility and proving the product worked under real conditions. 🔍 Validate by talking to every stakeholder, not just buyers: Adam spoke with dozens of companies and auditors before writing code, discovering identical pain patterns that made the initial product scope obvious. 🤝 Give before you take with strategic partners: Drata brought thousands of first-time customers to AWS Marketplace before asking for anything in return, becoming a top 5 global ISV in under two years. 📉 Selling a vitamin versus a painkiller changes everything: Seven years in edtech taught Adam what product-market fit feels like when you don't have it. At Drata, customers lined up because compliance wasn't optional. 🚀 Reassemble a proven team to compress execution time: Adam brought back the same co-founders, engineers, and go-to-market team from Portfolium. The muscle memory from working together for 7 years accelerated every phase of Drata's launch. 🏢 Keep partners independent to build a distribution moat: Drata's Auditor Alliance kept audit firms independent rather than competing with them. Two-thirds of Drata's pipeline is now sourced or influenced through partner channels. Chapters Introduction What Drata does and the trust problem it solves Revenue, customers, and team size From astronaut dreams to NASA's Space Shuttle program Building Portfolium after NASA retired the shuttle Teaching himself to code and finding a CTO Selling Portfolium for $43 million The long road to product-market fit in edtech The university sales cycle that changed everything How the Portfolium pain led to founding Drata Validating the problem before writing code Getting the band back together Using Drata to get their own SOC 2 before selling Signing 100 customers in six weeks How Drata differentiated in a crowded market What broke at 1,000 customers Building the Auditor Alliance partner program The AWS Marketplace strategy and give-before-you-take Why aggressive sales culture was intentional AI tailwinds for compliance and trust Lightning round Closing thoughts 💌 Get weekly 5-minute SaaS insights: https://saasclub.io/email SaaS Club Programs Join the SaaS Club founder community: https://saasclub.co/plus Build your $10K MRR SaaS: https://saasclub.io/launch Scale from 6-figures to $1M ARR Faster: https://saasclub.io/mastermind Get 1:1 async coaching from Omer: https://saasclub.io/accelerate Resources Full show notes: https://saasclub.io/471 Subscribe to the podcast: https://saasclub.io/subscribe
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    1 hr and 2 mins
  • Product-Market Fit: From a School Project to $20M ARR

    Product-Market Fit: From a School Project to $20M ARR
    Feb 12 2026
    $2M to $9M ARR in one year. Then it nearly fell apart. Gilles Bertaux expanded Livestorm into meetings and sales demos after COVID, turning it into a smaller Zoom with no clear differentiator. In this episode, founders will learn how he rebuilt product-market fit by narrowing to a niche most would run from. Gilles shares why 85% of customers on monthly plans was a ticking time bomb, how a failed Series C forced the right strategic shift, and why targeting marketers instead of IT buyers let Livestorm avoid competing with Zoom on budget. Livestorm generates nearly $20 million in ARR with 3,500 customers and has raised $35 million. Gilles co-founded the company in 2016 as a university project and has led it through explosive COVID growth, a near-collapse in positioning, and a rebuild to product-market fit with enterprise buyers. This episode is brought to you by: 🌎 ThreatLocker → Book a demo 💖 Gearheart → Book a free consult and get the first 20 hours free 🔑 Key Lessons 🎯 Product-market fit can be lost by expanding too broadly: Livestorm added meetings and sales demos after COVID, turning into a smaller Zoom with no clear differentiator. The longer the sales conversation, the lower the conversion rate. 📉 Explosive growth can mask a fragile customer base: Going from $2M to $9M ARR in one year felt like traction, but 85% of customers were on monthly self-serve plans. One button click and that revenue disappears overnight. 🏢 Narrow positioning wins against giants: Livestorm stopped competing feature-for-feature with Zoom and differentiated on three dimensions - European company for security-conscious buyers, marketers only to avoid IT budgets, and specific industries like banking and pharma. 🔄 Selling to enterprise requires rebuilding the sales team, not retraining it: Reps who closed inbound leads from a CRM could not cold-call 10,000-person companies. Gilles had to replace almost the entire original sales team with people experienced in enterprise outbound. 💰 A failed fundraise can force the right strategic shift: When Series C investors said no in 2022, Livestorm had to become profitable. That constraint pushed them toward enterprise customers on annual contracts who pay more and stick longer. 🛠️ Target the buyer with a separate budget: By positioning Livestorm as a marketing tool instead of an IT tool, Gilles avoided budget wars with Zoom and Teams. Marketers control their own spend and do not need IT approval to buy. Chapters Introduction What Livestorm does and who it serves Revenue, customers, and funding Building Livestorm as a university project The disastrous first webinar launch Why a product launch is a timeline, not a day Finding the first 10 customers through inbound SEO, Quora, and co-marketing as early growth engines Competing with GoToWebinar and Zoom How product-market fit shifted after COVID Going from $2M to $9M ARR in one year Support tickets from 200 to 20,000 and servers crashing Post-COVID churn and the virtual event collapse Why webinars survived but virtual events died Losing product-market fit by becoming a smaller Zoom Rebuilding positioning around Europe, marketers, and industries Why video is a commodity and experience is the differentiator How Livestorm processes 4,000+ feedback items per quarter The painful shift from PLG to enterprise sales Rebuilding the sales team for outbound From tech nerd to startup CEO Lightning round 💌 Get weekly 5-minute SaaS insights: https://saasclub.io/email SaaS Club Programs Join the SaaS Club founder community: https://saasclub.co/plus Build your $10K MRR SaaS: https://saasclub.io/launch Scale from 6-figures to $1M ARR Faster: https://saasclub.io/mastermind Get 1:1 async coaching from Omer: https://saasclub.io/accelerate Resources Full show notes: https://saasclub.io/470 Subscribe to the podcast: https://saasclub.io/subscribe
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    1 hr and 2 mins
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