The SaaS Podcast - AI, Growth & Product-Market Fit for SaaS Founders

Omer Khan
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Every week, SaaS founders share how they found product-market fit, got their first customers, scaled to $1M+ ARR, and navigated pricing, sales, churn, and AI. Host Omer Khan has interviewed 500+ founders and coached 150+ through revenue milestones. Whether you're bootstrapping to $10K MRR or scaling past $1M+ ARR, The SaaS Podcast delivers proven growth strategies - not theory. Join 5,000+ founders at SaaS Club. New episodes weekly.

  1. 5D AGO

    Enterprise Sales: How Egnyte Competed Against Box and Dropbox

    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

    51 min

  2. FEB 19

    Product-Market Fit: Adam Markowitz From $45M Exit to $100M

    Seven years selling a nice-to-have. Then 100 customers in six weeks. Adam Markowitz spent years pushing an edtech product before realizing he'd never had real product-market fit. When he built Drata, prospects lined up - 1,000 customers in year one and $100M ARR before the fourth birthday. Adam reveals why he refused to sell until his team used Drata for their own SOC 2 compliance, the "give before you take" AWS strategy that made Drata a top 5 ISV on Marketplace in under two years, and why an aggressive sales culture was an intentional design choice. Plus: how the CIO who challenged Adam's security posture at his first startup planted the seed for market validation that eventually became Drata. Drata is a trust management platform with 8,000+ customers across 60 countries, 600+ employees, and over $300M raised. Adam's journey from NASA engineer to edtech to PMF at Drata is a masterclass in recognizing what product-market fit actually feels like. This episode is brought to you by: 🌎 ThreatLocker → Book a demo 🔑 Key Lessons 🎯 Product-market fit shows in buyer urgency, not signups: Drata signed 100 customers in 6 weeks and 1,000 in year one - versus years to close the first 5 university customers in edtech. 🛠️ Dogfood your product before selling it: Drata refused to accept customers until they used their own tool to get SOC 2 compliant, giving instant credibility and proving the product worked under real conditions. 🔍 Validate by talking to every stakeholder: Adam spoke with dozens of companies and auditors before writing code, discovering identical pain patterns that made the initial product scope obvious through market validation. 🤝 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. 📉 Product-market fit means selling a painkiller, not a vitamin: Seven years in edtech taught Adam what a nice-to-have feels like. At Drata, customers lined up because compliance was blocking their deals - a clear sign of PMF. 🚀 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. 🏢 Keep partners independent to build a distribution moat: Drata's Auditor Alliance kept audit firms independent rather than competing with them. Two-thirds of pipeline is now sourced or influenced through product-market alignment with 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 Resources Full show notes: https://saasclub.io/471 Join 5,000+ SaaS founders: https://saasclub.io/email

    1h 2m

  3. FEB 12

    Product-Market Fit: How Gilles Bertaux Rebuilt at $9M ARR

    $2 million to $9 million ARR in a single year. Then Gilles Bertaux nearly destroyed everything. He expanded Livestorm into meetings and sales demos, turning it into a smaller version of Zoom. Customers had no reason to choose them. A failed Series C forced the team to rebuild product-market fit from scratch - by narrowing to enterprise webinars for European marketers in banking and pharma. Gilles reveals how COVID growth masked a fragile customer base (85% on monthly plans), why losing product-market fit taught him more than finding it, and the three positioning decisions that rebuilt PMF: being European for security-conscious buyers, targeting marketers to avoid IT budgets, and focusing on industries where webinars are a weekly strategy. Plus: how Gilles wrote 3-4 SEO articles per day in the early days and used Quora to drive 10-15% of organic traffic for five years - a market validation channel nobody else was using. Livestorm generates nearly $20M ARR with 3,500 customers. Gilles shifted from 85% monthly self-serve to predominantly enterprise annual contracts after achieving product-market alignment through narrow positioning. 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. 🏢 Narrow positioning wins against giants: Livestorm stopped competing feature-for-feature with Zoom and differentiated on three dimensions - European company for security, marketers only to avoid IT budgets, and specific industries for market validation. 🔄 Selling to enterprise requires rebuilding the sales team: Reps who closed inbound leads could not cold-call enterprise companies. Gilles replaced almost the entire original sales team with people experienced in enterprise outbound. 💰 A failed fundraise can force the right product-market fit shift: When Series C investors said no in 2022, Livestorm had to become profitable. That constraint pushed them toward enterprise customers 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. Marketers control their own spend and product-market alignment improves when you sell to the right buyer. 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 Resources Full show notes: https://saasclub.io/470 Join 5,000+ SaaS founders: https://saasclub.io/email

    1h 2m

  4. FEB 5

    Bootstrapped SaaS: How Adam Fard Hit $5.3M ARR in 18 Months

    Every wireframing tool claimed to use AI. They were all faking it. Adam Fard tested them and discovered they just swapped templates. The real technical challenge - generating wireframes from scratch - was too hard. So he built it himself. He bootstrapped UX Pilot from a Figma plugin side project to $5.3M ARR in under two years, growing from $3M to $5.3M in just 5 months, without a single dollar of funding. Adam reveals how he used agency revenue to bootstrap the SaaS without VC pressure, why talking about product updates got more newsletter engagement than educational content, and the self-funded SaaS hiring mistake at $30K MRR that cost him months of velocity. UX Pilot is a bootstrapped SaaS platform that helps professional product design teams create and ship user experiences faster using AI. Adam grew it to 15,000 paying subscribers with a 600,000-subscriber newsletter and a profitable SaaS model. 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 🎯 Test competitor claims before building your bootstrapped SaaS: Adam discovered other wireframing tools were faking AI generation by swapping templates - revealing a genuine technical opportunity others couldn't solve. 💰 Bootstrap with existing revenue streams: Adam used his UX agency income to fund UX Pilot development, removing pressure to raise funding or hit arbitrary milestones - the self-funded SaaS advantage. 🚀 Focus on one hard problem: While competitors built no-code tools that did everything, Adam focused exclusively on AI wireframe generation. This focus built a profitable SaaS faster than going broad. 📈 SEO still works for bootstrapped SaaS: Despite advice that "SEO is dead," Adam got significant traffic from high-intent keywords by being one of the first to target "design, UX and AI generation." 🧠 Hire faster than feels safe when bootstrapping: Adam's biggest regret was hiring 1-2 people at $30K MRR instead of 5 at once - the slow process cost months of velocity and prolonged the bootstrap struggle. 🛠️ Talk about your product, not just "valuable content": Adam got more newsletter engagement sharing UX Pilot updates than generic education. People want to know what you're building. 🔄 Code-first architecture creates competitive moats: By outputting code instead of vector graphics, UX Pilot eliminated conversion steps, making it faster for developers and harder for competitors to replicate. Chapters Introduction What UX Pilot does and who it's for Revenue, team size, and growth metrics Running a UX agency when ChatGPT launched The user question that sparked the product idea Testing competitors and discovering they were faking AI Getting early users to do discovery sessions Why creating wireframes with AI was technically hard Building an MVP that had nothing in common with the current product Exploring fine-tuning LLMs and component-based approaches What the first paying customer version looked like Building a 600K subscriber newsletter from product signups Why talking about product updates got more engagement than education Getting to the first million in ARR with LinkedIn, newsletter, and SEO Posting 3-4 times per week on LinkedIn The mistake of hiring too slowly when bootstrapping The inflection point from $3M to $5.3M ARR in 5 months Focusing on enterprise teams vs trying to target everyone Lightning round Resources Full show notes: https://saasclub.io/469 Join 5,000+ SaaS founders: https://saasclub.io/email

    51 min

  5. JAN 29

    Product-Market Fit: Tito Goldstein's 2-Year Pivot to Growth

    Two Uber product designers. $3 million raised. Two years of near-zero revenue. Tito Goldstein built a scheduling tool that nobody wanted to buy. Then he threw it out and rebuilt TeamBridge as composable Legos - and the new product outsold two years of work in its first month. Founders will hear how finding product-market fit required listening to what customers didn't say. Tito reveals why customers kept asking for features while the real pain was "I need to stand out, not use the same software as competitors," how the composable approach turned TeamBridge into a market validation win for staffing agencies and stadiums, and why casting too wide a net delayed PMF by years. Plus: how one medical staffing agency went from zero admin staff to a multimillion-dollar business using TeamBridge - proof that product-market alignment creates compounding growth. TeamBridge is a composable workforce operating system serving over 500,000 employees across 200+ enterprise customers, including NFL stadiums like the 49ers' Levi's Stadium. 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 🎯 Listen to what customers don't say to find product-market fit: TeamBridge's buyers kept asking for features, but the real pain was "I need to stand out, not use the same software as my competitors." The PMF breakthrough came from reading between the lines. 📉 Throw out sunk cost when the market speaks: Tito and Arjun spent 2 years building a scheduling tool that failed. Instead of iterating, they threw it out and rebuilt - outselling 2 years of work in the first month. 🛠️ Composability beats cookie-cutters for product-market fit: In supply-constrained industries, off-the-shelf tools make companies commodities. Customizable workflows became the market validation point that competitors missed. 💰 Stay lean until product-market fit: TeamBridge kept burn low with a team of 5-6 and multiple years of runway. That gave them freedom to pivot without investor pressure. 🚀 Your first product validates the problem, not the solution: The initial scheduling tool failed, but it uncovered the real pain: connective tissue (automations, workflows) mattered more than core features. 🤝 Be honest in early-stage messaging: Instead of pretending to have all the answers, Tito pitched: "We built amazing tech at Uber, now we want to bring it to your industry." The right early adopters leaned into that honesty. 🔄 Focus narrows as you find product-market fit: TeamBridge cast a wide net to learn, but once they found traction with medical staffing, they doubled down. Product-market alignment requires choosing. Chapters Introduction and favorite quotes What TeamBridge does and who it serves Why composability matters for workforce software Size of the business: revenue, customers, team Origin story: interviewing Uber drivers Going door-to-door to understand hourly worker pain Raising $3M seed with just a prototype Why it took 2 years to find product-market fit The pivot: from scheduling to composable Legos First significant sale during COVID Biggest objections: explaining composability Finding the right messaging and storytelling Downsides of casting too wide a net Moving upmarket to enterprise customers How COVID forced TeamBridge to mature go-to-market Cold email lessons: honesty and relationship building Discovery-first selling: hold the pitch until you know the pain Learning the nuances of each vertical Lightning round: grit, curiosity, and fitness Resources Full show notes: https://saasclub.io/468 Join 5,000+ SaaS founders: https://saasclub.io/email

    45 min

  6. JAN 22

    First Customers: How Nate Baker Grew Qualia to $100M ARR

    He wore a Stanford sweatshirt to a conference. Five minutes later, he had his first customer. Nate Baker found his first customers through network selling, not cold outreach - then lived in that customer's basement for a year. That relationship set the foundation for Qualia's growth to $100M ARR. Nate reveals why the first 25 Qualia employees rotated through Barry's basement to learn the industry, the multi-year upfront contracts that brought forward $100K in cash at just $45K ARR, and the wake-up call when a VP of Sales said: "I've never seen such a gap between great product and incompetent sales execution." Qualia is a title software platform generating over $100M in ARR with 600 employees and $200M+ raised. Nate started building at 21 with zero real estate experience and found his early customers entirely through network-based relationships. This episode is brought to you by: 💖 Gearheart → Book a free consult and get the first 20 hours free 🔑 Key Lessons 🤝 First customers must come from network selling: Nate says your first 10 customers have to be in-network sales. Barry introduced Qualia to his competitors, building the foundation for their initial traction. 🏠 Embed yourself with first customers to learn their world: Nate and the first 25 Qualia employees rotated through living in Barry's basement. "To actually understand what your customer does, you just have to be so in it." 💰 Use multi-year upfront contracts to align incentives: Qualia offered 5-year contracts at 80% discounts, collecting $100K upfront from first paying users when they had just $45K ARR. 🗺️ Geographic focus beats national expansion for early customers: Qualia stayed in Massachusetts for the first year, building density and network effects in one state before expanding. ⚡ Crisis creates your most productive moments: When Barry's vendor shut him off overnight, Qualia didn't have core features built. That pressure became "the most productive month in company history." 🔧 Hire sales leadership before you think you're ready: At $45K ARR, Qualia's VP of Sales exposed the gap between great product and incompetent execution. Within 12 months they hit $3.5M ARR. 🎯 Pick markets where incumbents are complacent: Baker used 10 selection heuristics to find industries with coordination pain, network effects, and competitors who weren't investing in technology. Chapters Introduction and what Qualia does How Nate picked the title software market at 21 with no experience The academic approach to market selection (and why it was a mistake) The real problem: coordination across multiple stakeholders Finding first customer Barry Feingold at a conference Living in Barry's basement for a year When Barry's vendor shut him off overnight How long it took to ship the first version Why narrow geographic focus beats national expansion early Early customer conversations and what they actually needed How to get first customers to pay before you've built the product The multi-year upfront contract strategy Network-based selling vs cold outreach for first customers The wake-up call: "Great product, incompetent sales execution" Moving upmarket and the "you don't understand Texas" objection Strategy for geographic expansion state by state When Nate realized they had real traction How the opportunity looks today with AI Lightning round Resources Full show notes: https://saasclub.io/467 Join 5,000+ SaaS founders: https://saasclub.io/email

    52 min

  7. JAN 15

    Enterprise Sales: How Yosef Peterseil Landed McDonald's

    A cold text to a stranger's phone number. Nine months just to close the POC paperwork. Yosef Peterseil landed McDonald's as his first enterprise sales customer while bootstrapping with zero revenue. The lesson: charging even $3,000 for a POC completely changes the dynamics of closing deals. Yosef reveals why their original ICP of customer success managers had no budget, how 70 hard-earned event leads went cold because they had no follow-up system, and the 13-month contract structure that eliminated double-negotiation traps in B2B sales cycles. Blings is a personalized video platform serving enterprise customers including McDonald's, Mercedes, Meta, and Rocket Mortgage. The company hit $1M ARR in 2023 with a team of 19. This episode is brought to you by: 💖 Gearheart → Book a free consult and get the first 20 hours free 🔑 Key Lessons 🎯 Validate ICP budget before building your enterprise sales motion: Yosef interviewed dozens of customer success managers before discovering they had no budget - pivoting to marketing where the money actually was saved months of wasted effort. 💰 Always charge for enterprise sales POCs: Even $3,000-$5,000 forces customers to prioritize your project, starts vendor onboarding, and signals they're serious about closing deals rather than just exploring. 📄 Combine POC and commercial into one contract: Yosef lost months negotiating POC terms only to negotiate again for the commercial deal - 13-month contracts with first-month exit clauses eliminated the double-negotiation trap. 📉 Build follow-up systems before generating leads: Blings spent $20K-$30K on a conference and captured 70 leads, but had no lead scoring or HubSpot sequences - the entire investment was wasted. 🤝 Don't hire salespeople without a documented playbook: A great salesperson closing deals proves their skill, not your product. Wait until a mediocre rep can follow your process and close enterprise sales consistently. 🎤 Go big at fewer events instead of small at many: Instead of spreading thin across 10 events, Yosef invested in speaking slots and masterclasses at 3 - generating higher quality B2B sales leads. 🔗 Use channel partners to scale enterprise sales doors: Recruiting industry veterans to open doors for recurring commission scaled Blings faster than direct sales alone. Chapters Introduction and favorite quote What Blings does - the MP5 video format Company metrics and enterprise customers The origin story and co-founder relationship Validating the ICP through customer interviews Pivoting from customer success to marketing Landing McDonald's through a cold text Closing the first enterprise sales POC Lessons from POC agreements Why you should always charge for POCs Event marketing mistakes - 70 lost leads Building a lead follow-up system Hiring salespeople too early Building channel partner relationships Scaling with 19 people Launching PLG motion Lightning round Resources Full show notes: https://saasclub.io/466 Join 5,000+ SaaS founders: https://saasclub.io/email

    46 min

  8. 12/11/2025

    Enterprise Sales: How Bassem Hamdy Closes Deals in 9 Days

    Most founders think enterprise sales takes 6-12 months. Bassem Hamdy closes deals in 9 days. After scaling Procore from $10M to $100M, Bassem built Briq - an AI workforce platform now doing 8 figures in revenue. His enterprise sales strategy is counterintuitive: never demo the product early, never do free POCs, and always charge from day one, even if it's just a dollar. Bassem reveals why he sells vision and value before showing a single screen ("I could demo a blank screen - they don't know what you're demoing anyway"), how targeting CFOs instead of innovation teams compresses B2B sales cycles, and the land-and-expand playbook that grew a $15K first deal into 8-figure enterprise sales revenue. Briq is an AI orchestration platform for construction and manufacturing that automates back-office work for enterprise customers including Fortune 100 companies. Bassem spent 15 years in construction tech before selling to enterprise in this market. This episode is brought to you by: 💖 Gearheart → Book a free consult and get the first 20 hours free 🔑 Key Lessons 🏢 Enterprise sales starts with vision, not demos: Bassem says "I could demo a blank screen" - customers don't know what they're looking at anyway. Align on vision and value first, and deal cycles shrink from months to days. 💰 Never do free POCs - even $1 creates commitment: Free pilots attract time-wasters. The moment money changes hands in B2B sales, prospects become invested in making the product work. 🎯 Target CFOs, not innovation teams: Innovation teams have shiny objects but no budget authority. CFOs control the checkbook, love price certainty, and can close enterprise sales quickly once they see ROI. 🔥 Fire bad enterprise customers before they sink you: A big logo can put you out of business as easily as put you on the map. If they're not ICP-aligned, cut them loose before they consume resources. 📈 Land small, expand fast: Briq's first deal was $15K. Through land-and-expand, they grew to 8 figures selling to enterprise. Start with one department, prove ROI, then expand across the organization. 💸 Consumption pricing enables natural expansion: Unlimited pricing is easy to sell but kills expansion. Consumption-based pricing lets enterprise customers grow without re-selling. 🔄 Don't pivot away from product-market fit: Briq had PMF with their automation product but pivoted to forecasting under investor pressure - and had to "refound" the company to recover. Chapters Why SaaS Founders Should Ignore Feature Requests Introduction and Welcome Is AI "Human Replacement" Software? The "Construction Data Cloud" Idea (And Why It Failed) Finding the Wrong ICP The "Agile" Trap: Why Most Product Teams Are Waterfall The Investor-Forced Pivot to Forecasting How to Close Enterprise Sales Deals in 9 Days Selling on "Vision and Value" vs. Features SaaS Pricing: Moving to Tokenization and Consumption First Price Was $15K - And It Was Too Cheap CFO Sales: Overcoming Risk Aversion Building Trust with Industry Associations Firing Bad Enterprise Clients Land and Expand Strategy Lightning Round Resources Full show notes: https://saasclub.io/465 Join 5,000+ SaaS founders: https://saasclub.io/email

    50 min
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About

Every week, SaaS founders share how they found product-market fit, got their first customers, scaled to $1M+ ARR, and navigated pricing, sales, churn, and AI. Host Omer Khan has interviewed 500+ founders and coached 150+ through revenue milestones. Whether you're bootstrapping to $10K MRR or scaling past $1M+ ARR, The SaaS Podcast delivers proven growth strategies - not theory. Join 5,000+ founders at SaaS Club. New episodes weekly.

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