Omer Khan
The SaaS Podcast - Real Lessons on Growing Profitable SaaS
Building software is easier than ever. Growing it into a profitable business is the hard part. Every week, a founder gets specific about what actually moved the needle: finding product-market fit, landing customers, pricing, defensibility, and durable growth. Host Omer Khan has interviewed nearly 500 software founders, from their first customers to real scale. You get what actually worked, not theory. Lately that includes the honest take on AI: what it changed about building and selling software, and what it didn't. New episodes every week.
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Episodes
Failed Software Startup: 10 Products Before PMF 17.03.2022 46:31
Jeb Banner built almost a dozen products that went nowhere over 12 years. His failed software startup streak broke only when he separated product from his agency and found product-market fit targeting nonprofits. Learn why a failed software startup inside an agency never survives, how Boardable achieved product-market fit by targeting nonprofit boards, and what hidden conversion signals a data sci...
Niche SaaS: Handwritten Letters to $9M ARR 10.03.2022 47:32
Tom Staff bought a PHP textbook and taught himself to code. That side project became Street Group, a niche SaaS for UK estate agents now doing over $800K MRR - all built on vertical SaaS principles. Learn how Heather and Tom used handwritten letters, exclusivity pricing, and deep industry-specific SaaS knowledge to build a niche SaaS to $9M+ ARR with zero outside funding. Heather is the co-founder...
B2B Product-Market Fit: 3 Years Lost, Then Breakout 03.03.2022 47:55
Khadim Batti spent three years building a product nobody needed. Then he deleted it and started finding product-market fit from zero. The SaaS pivot turned a support tool into a $600M company. Learn how Khadim achieved B2B product-market fit by sending 500 cold emails, closing before writing code, and narrowing from SMB to enterprise CRM for product validation. Khadim is the co-founder of Whatfix,...
SaaS Retention: From 2% Survey Response to Full Fix 24.02.2022 37:43
Tony Sternberg launched ProsperStack with a post-cancellation survey. Only 2% responded. That's when he realized his entire approach to SaaS retention and SaaS churn was wrong. Discover how Tony rebuilt ProsperStack as an embedded cancellation flow for real-time SaaS retention, achieving churn reduction by intercepting 100% of cancel actions at the moment they happen. Tony is the co-founder of Pro...
SaaS Product Validation: 5 Interview Tactics That Work 17.02.2022 44:35
Most founders think they know what problem their product solves. Michele Hansen's SaaS product validation framework proves them wrong through customer interviews and customer discovery. Learn Michele's approach to SaaS product validation - from finding product-market fit signals to the 'reaching for the door' question, and why 5 customer interviews reveal enough to act. Michele is the co-founder o...
SaaS Branding: No Category Name Cost Years of Sales 10.02.2022 49:27
Benn Stancil built a product customers loved but nobody could name. Mode's SaaS branding fell between BI dashboards and data science tools - a SaaS positioning problem that confused buyers for years. Learn how Mode solved its SaaS branding challenge by narrowing to 'by analysts, for analysts,' using entertainment-first content for product positioning, and growing to 8-figure ARR. Benn is the co-fo...
Product-Led Growth: $19/Year Pricing to $1M ARR 04.02.2022 53:24
AJ started Carrd as a vanity project to pay for lattes. Using product-led growth and freemium SaaS pricing at $19/year, he grew to $100K MRR and 4 million sites with just two people. Learn how AJ built a product-led growth engine using the freemium model, built-in virality through 'Made with Carrd' links, and a product-led growth approach that replaced all marketing spend. AJ is the founder of Car...
Startup Funding: 5 Capital Raising Mistakes to Avoid 27.01.2022 40:02
Brian Parks raised $30M for Bigfoot Capital and has funded 35 B2B SaaS companies. His conclusion: most startup funding fails because founders treat capital raising like a side project instead of a SaaS fundraising priority. Learn the 5 startup funding mistakes founders repeat and the 8-step process Brian uses on both sides - as someone who manages SaaS fundraising and deploys venture capital SaaS...
B2B SaaS Sales: 4 Years to Crack Enterprise Deals 20.01.2022 38:11
Jody Glidden spent four years solving a CRM data problem before B2B SaaS sales took off. His enterprise sales cycles dragged three years to close a single deal through founder-led selling. Learn how Introhive cracked B2B SaaS sales by focusing on one vertical, doing founder-led selling for 4 years, and building SaaS partnerships that grew revenue from 7% to 30%. Jody is the co-founder of Introhive...
Selling SaaS Without Sales Experience: $0 to $1M 15.12.2021 43:26
Mitch Causey had no sales background when he started selling SaaS without sales experience. He ran a one-person SEO agency using spreadsheets, then turned those into software and grew DemandWell to $1M+ ARR. Learn how Mitch built a SaaS sales process by selling SaaS without sales experience first, pre-selling software before it existed, and developing a founder-led sales playbook before hiring rep...
Recurring Revenue: Triple Prices, Cut Churn to 2% 08.12.2021 58:07
Jordan Gal built CartHook into a $6M ARR recurring revenue machine on Shopify. Then Shopify shut him down. But before that, his SaaS pricing strategy of tripling prices transformed a leaky business into a healthy one. Discover how raising recurring revenue prices from $99 to $500 plus transaction fees achieved churn reduction from 15% to 2% and doubled MRR from $250K to $500K in one year. Jordan i...
Selling a SaaS Business: Buy at $500K, Sell 3x 30.11.2021 50:45
Raj Sheth bootstrapped RecruiterBox to $4M ARR, sold to private equity, and then built a SaaS factory focused on buying and selling SaaS businesses. His first SaaS acquisition returned 3x in 13 months. Learn how Raj evaluates SaaS companies at $1-3M ARR, turns them around with a SaaS turnaround playbook, and positions each one for selling a SaaS business at a premium. His system targets 50% EBITDA...
Starting a SaaS: 8 Founders From 6 Countries Share Lessons 24.11.2021 20:06
What happens when eight founders starting a SaaS from Germany, New Zealand, Louisiana, San Francisco, South Africa, India, Florida, and France all share their stories? You hear what it really takes to keep going when you feel alone, broke, and unsure if anyone will ever use your product. For the 300th episode of The SaaS Podcast, host Omer Khan invited eight listeners who are starting a SaaS to sh...
SaaS SEO Strategy: The Link Building Playbook That Works 28.10.2021 58:22
Most SaaS companies invest heavily in content creation and then do nothing to promote it. Alan Silvestri built an entire agency around fixing that SaaS SEO strategy gap - and his outreach email was so good it landed him on this podcast after Omer initially said no. In this episode, Alan walks through his exact SaaS SEO strategy for link building and content promotion. He explains why most outreach...
SaaS Go-to-Market: One Niche Built a $20M Business 20.10.2021 48:36
Dave MacLeod spent years trying to sell to everyone and got nowhere. Then he focused his SaaS go-to-market on one niche SaaS market - school districts - and that single decision built a $20M business. For almost five years, ThoughtExchange focused exclusively on K-12 education. That SaaS go-to-market discipline gave them sharp messaging, passionate customer advocates, and a product purpose-built f...
Enterprise Sales: $2K MRR to 7 Figures With Cold Email 30.09.2021 45:47
Santi Bibiloni was stuck at $2K MRR selling to small agencies. Then he shifted his enterprise sales strategy upmarket and started closing multi-year contracts with some of the largest agencies in the world. In this episode, Santi reveals how COR went from offering free trials and monthly plans to eliminating free trials entirely, selling annual and multi-year contracts to CFOs, and growing to betw...
Freemium SaaS: 18 Months to 10 Customers Then Liftoff 24.09.2021 43:42
Jon Fagg spent 18 months struggling to get 10 paying customers. Then he introduced a freemium SaaS model, and within six months, Skedda had more signups than they had managed in the previous two years combined. In this episode, Jon reveals how Skedda grew from a side project that three part-time co-founders built across time zones into a bootstrapped 7-figure business with 4,000 paying customers....
Venture Capital SaaS: Two Teens Raised From Calacanis 16.09.2021 47:55
Most venture capital SaaS stories start in Silicon Valley with decades of experience. Liam Gerada did it at 19 from a small island in the Mediterranean - with zero coding skills and a brother who was still a teenager. In this episode, Liam reveals how he and his brother Travis built Krepling, a Shopify competitor, from scratch after their own e-commerce struggles. He shares the venture capital Saa...
Startup Traction: From 0 Customers to $12M ARR and Exit 09.09.2021 59:20
Ryan Fyfe couldn't get 10 customers to pay for his scheduling software. People seemed interested but always had an excuse. Then his co-founder left and he became a solo founder of a product that nobody wanted to pay for. Getting startup traction felt impossible. But after years of persistence, Ryan bootstrapped Humanity to $100K ARR, raised funding, and grew it to $12M ARR with 40,000 customers in...
SaaS Pricing: From $79 to $500 Against Free Competitors 02.09.2021 53:49
Iris Shoor got her first customer 30 minutes after turning on Facebook ads - for less than $50. The product was clearly working. Then she killed it. She shut down a product with real users, real engagement, and real validation because investors told her Facebook would build it themselves. In this episode, Iris reveals the SaaS pricing journey that took Oribi from free to $79 to $500 per month, why...
SaaS Sales Strategy: 500 Handwritten Letters to 7 Figures 07.07.2021 52:20
Zandra Moore and her co-founders carried a server across a car park to start their company. Then they wrote 500 handwritten letters to software vendors - because in a market dominated by Tableau and Power BI, their SaaS sales strategy meant doing things nobody else would. In this episode, Zandra reveals how Panintelligence grew into a multiple 7-figure SaaS business with 50+ employees by embedding...
Product-Led Growth: 2 People, No Funding, Nearly $1M ARR 30.06.2021 53:24
Esben Friis-Jensen went from co-founding a VC-backed security company with 200 employees and $37 million in funding to a bootstrapped product-led growth startup with just two people - and nearly $1M in annual recurring revenue. In this episode, Esben reveals how a single customer request triggered Cobalt's pivot from bug bounty to pen testing, why he chose to bootstrap Userflow after years in the...
Niche SaaS: Bar Surveys to $2M ARR Leasing Platform 23.06.2021 47:59
Steve Carroll sent his co-founder into New York bars to ask strangers how they paid their rent. Some women thought it was a pickup line - until they saw the Typeform survey. That scrappy approach got them 1,000 survey results and enough conviction to build a niche SaaS product for the rental market. In this episode, Steve reveals how Findigs pivoted from a consumer rent payments app to a B2B niche...
Startup Funding: Landing Page to 60K Users to 1.2M Raised 02.06.2021 53:46
Holly Stephens built a landing page in 24 hours for a product that didn't exist - just a description of a tool that would make it easier to add subtitles to videos. She posted it in Facebook groups and had 50 signups within days. That validation was enough to start building - and eventually secure startup funding. Within 18 months of launching, Subly had 60,000 users and Holly had completed her st...
SaaS Monetization: From Free API to Multi-Million ARR 26.05.2021 52:28
Ben Dowling built a free API over a weekend to save himself time looking up IP addresses. A year later, he reluctantly added SaaS monetization plans starting at $50/month - and was shocked when someone immediately signed up for the $200 plan. The bigger shock came when enterprise companies started asking for sales calls, and he kept turning them away. Today IPinfo handles 40 billion API requests a...
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