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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Episoder
SaaS Pricing for Exits: Sell Your Business for 4-8x 16.05.2024 52:30
Juan Ignacio Garcia tried to acquire three SaaS businesses and failed every time because nobody would finance the deal. So he built Boopos, a marketplace with built-in acquisition financing. Most SaaS businesses sell for 4-8x profit multiples - but SaaS pricing for your exit depends on retention, financials, and deal strategy. Learn the complete playbook for SaaS pricing when selling a SaaS busine...
SaaS Partnerships: Two Exits to 19,000 Companies 09.05.2024 1:07:02
Bob Moore quit his VC job the day before Lehman Brothers collapsed. He bootstrapped RJ Metrics, sold it to Magento, then spun out the same technology as Stitch and sold it for $60M in 18 months. Now his SaaS partnerships platform Crossbeam serves 19,000 companies at 8-figure ARR. Learn how to sell the same company twice, why SaaS partnerships require solving the cold start problem with joint onboa...
SaaS Sales Process: From Failed Outbound to 7-Figures 02.05.2024 51:15
Lars Gronnegaard left Trustpilot with a clear SaaS sales process plan. Then reality hit. His first 10 customers looked nothing like the ICP. Cold outreach needed 180 days to show results. It took a LinkedIn content strategy hitting 300,000 views to finally reach 7-figure ARR. Learn how a documented SaaS sales process replaced tribal knowledge, why 28-day outbound cycles beat 180-day sequences for...
B2B SaaS Sales: 5 Years to Build What Oracle Said Was Impossible 25.04.2024 59:54
Thomas Cottereau spent five years building what Oracle's engineers said was technically impossible. When he demoed the B2B SaaS sales platform at Salesforce, a lead engineer tested every feature by midnight and emailed: 'It works as you said. Come to my office tomorrow.' Learn how weekly office visits earned a strategic partnership for B2B SaaS sales, why HP saved millions using SightCall for remo...
Consultative Selling SaaS: 1,500 Demos to $19M ARR 18.04.2024 58:44
Andrew Guttormsen did over 1,500 one-on-one demos in 18 months - consultative selling SaaS the hard way. That personal touch turned Circle into a $19M ARR business. A single JV webinar with anchor customers like Pat Flynn drove 300 new customers in one push. Learn how consultative selling SaaS through founder-led demos built unstoppable word of mouth, why anchor customers accelerated the SaaS sale...
Selling SaaS Without Sales Experience: $2K to $25K 11.04.2024 46:05
Adam Gavish had never sold anything in his life. As a Google PM, he had to become DoControl's first SDR - selling SaaS without sales experience. He pitched 22 VCs in one week (21 said no), landed a first customer at $2K/year, and scaled deals to $25K+ by treating every call as a founder-led sales feedback session. Learn the playbook for selling SaaS without sales experience, how 50 validation inte...
Enterprise SaaS: From Rejection to Raising $72M 04.04.2024 49:08
An investor told Stephany Lapierre she would never raise capital. She had three kids, no tech background, and no co-founder. But she flipped that rejection into fuel, raised $72M in startup funding for TealBook, and built an enterprise SaaS platform serving over 100 Fortune 1000 customers. Learn how a non-technical founder overcame enterprise SaaS fundraising rejection, why the 'ZoomInfo for procu...
Scaling SaaS: $52K Investment to $22M ARR With SEO 28.03.2024 54:00
Jared Brown invested $52,000 with a stranger he met on LinkedIn. Eleven years later, Hubstaff generates $22M in ARR and SEO is still the engine scaling SaaS to 16,000 customers. COVID doubled revenue from $6M to $12M in just 12 months of SaaS growth. Discover how SEO alone drove scaling SaaS from zero to $22M ARR, why low pricing created viral bootstrapped growth loops, and how continuous onboardi...
SaaS Retention: How Narrowing Your Niche Reignites Growth 07.03.2024 53:32
Brennan Dunn raised $500K, grew RightMessage to $35K MRR in a year, then watched it all slide backward. For two years, SaaS retention flatlined and both co-founders lost motivation. The SaaS churn problem was clear - too broad a market and customers who lacked the data the product needed. Learn how narrowing niche positioning reignited SaaS retention, why hands-on onboarding turned a customer rete...
Enterprise Sales: Partner-First Strategy to 4,000 Customers 29.02.2024 1:01:17
Simon Taylor showed up at Nutanix headquarters wearing a bright white jacket with a red carnation - and nobody knew who he was. A year later, his enterprise sales through that partner-first strategy had delivered thousands of enterprise customers for HYCU across 78 countries. Learn how a partner-first strategy for enterprise sales replaced cold calling, why education-first content drew 2,000 webin...
SaaS Partnerships: $230K MRR With Zero Paid Marketing 22.02.2024 49:47
Ian Brodie and his co-founder quit their jobs in March 2020, got laughed out of every VC meeting, and built a services business instead. After selling it for a mid-7-figure deal, they launched Levanta and hit $230K MRR in 9 months through SaaS partnerships with affiliate agencies - without a dollar in paid marketing. Learn how SaaS partnerships drove 650 brands and 2,500 affiliates to one platform...
Self-Serve SaaS: From VR Failure to 7-Figure PLG 15.02.2024 55:53
Vlad Gozman spent two years building a VR product nobody wanted. Then he pivoted into one of the most crowded markets in SaaS - form builders - and grew a self-serve SaaS to 7-figure ARR with a 14-person team. Content marketing now drives 60-70% of revenue for this self-serve SaaS. Discover how involve.me differentiated in a crowded market, why a private lifetime deal beat AppSumo for funding this...
SaaS Positioning: From 80% Explaining to 4 Minutes 08.02.2024 57:38
James Evans spent 80% of every sales meeting explaining what Command Bar did. Nobody understood his SaaS positioning because he was trying to create a new category instead of fitting into an existing one. When he repositioned into digital adoption, discovery calls went from 25 minutes to 4 - and the company grew to 7-figure ARR. Learn why SaaS positioning in an existing market beats category creat...
SaaS Retention: From $1M ARR to 40% Monthly Churn 01.02.2024 47:45
Brett Martin and his co-founder hit $1M ARR in just two and a half months. Then SaaS churn nearly killed the business - 40% of customers disappeared in a single month. The SaaS retention crisis forced a complete pivot. In this episode, Brett reveals how Kumospace pivoted from a viral events platform to a virtual office serving millions of users. You will learn why SaaS retention problems were hidd...
Vertical SaaS: From Race Car Driver to 60 Airports 25.01.2024 52:38
George Richardson went from professional race car driver to vertical SaaS founder - and says building AeroCloud has been far harder than risking his life on the track. After two years building an airline app with zero traction, he pivoted to cloud-based airport management software. In this episode, George reveals how AeroCloud built a vertical SaaS business targeting niche SaaS opportunities in ai...
Scaling SaaS Solo: Two Products, No Funding, $10M ARR 18.01.2024 58:35
Michael Kamleitner spent over a decade scaling SaaS as a solo founder running two bootstrapped products in parallel. When the pandemic wiped out live events overnight, his social media aggregator Walls.io lost its core use case. In this episode, Michael reveals how he pivoted Walls.io into virtual events, built SaaS partnerships through a channel program that saved the company, and why running an...
Consultative Selling SaaS: Solo Founder to 8-Figure ARR 11.01.2024 1:12:11
Thejo Kote sold the first 15-20 Airbase customers through consultative selling SaaS - without a co-founder, without a sales team, and without writing code until 10 CFOs confirmed they would buy. That founder-led sales motion became the foundation of an 8-figure ARR company. In this episode, Thejo reveals how consultative selling SaaS to CFOs shaped Airbase's entire SaaS sales strategy. You will le...
SaaS Product Validation: 3 Years of Pivots to $60M ARR 04.01.2024 1:07:05
Greg Smith spent three years manually building online courses for customers one at a time before finding product-market fit for Thinkific. Then a single webinar converted 20 of 55 attendees into $1,000 paying customers overnight - the ultimate SaaS product validation moment. In this episode, Greg reveals how he and his brother went from a $29 LSAT prep course to a $60M ARR public company. You will...
SaaS Pricing: What AWS Taught This Founder About Billing 21.12.2023 59:49
John Griffin built a backend platform for game developers, sold it to Amazon, and then watched AWS run the most sophisticated usage-based pricing system on the planet. That experience sparked the idea for m3ter - and a new approach to SaaS pricing. In this episode, John reveals how m3ter helps software companies adopt usage-based pricing models, why going too broad with early customers nearly dera...
SaaS Positioning: How Picking One Customer Hit 8 Figures 14.12.2023 55:13
Duda was growing fast as a mobile website builder when Itai Sadan made a counterintuitive SaaS positioning decision - stop serving half the customer base and rebuild the core product from scratch. Revenue went flat for two years. In this episode, Itai reveals how that SaaS positioning bet turned Duda into an 8-figure ARR company with 22,000 agencies. You will learn why competitive differentiation...
B2B Community Building: Free Pizza to $10M ARR 07.12.2023 1:19:07
Lloyed Lobo sent hundreds of cold emails trying to sell Boast.ai's R&D tax credit platform. Nobody replied. Then he stopped selling and started hosting 10-person meetups with free pizza - and B2B community building carried the company past $10M ARR without a marketing team. In this episode, Lloyed reveals how community-led growth replaced traditional acquisition. You will learn how B2B community b...
B2B Product-Market Fit: 7 Years of Niching Down 30.11.2023 57:49
Stefan Debois spent seven years searching for the right niche before finding B2B product-market fit. The breakthrough came not from a grand strategy but from listening to customers who kept requesting the same feature - personalized PDF reports. In this episode, Stefan reveals how he pivoted Pointerpro from generic surveys to an assessment platform for professional services. You will learn why fin...
Selling SaaS Without Sales Experience to 7-Figure ARR 16.11.2023 53:39
Mang-Git Ng had zero sales background when he started Anvil. He spent 25 minutes agonizing over each cold email, barely got any responses, and attracted the wrong customers who demanded hand-holding for $5 a month. Selling SaaS without sales experience felt impossible. In this episode, Mang-Git reveals how he went from sweating over outreach emails to closing 7-figure ARR deals. You will learn how...
SaaS Content Marketing: Side Project to 7-Figure ARR 09.11.2023 56:00
Lukas Fittl spent seven years building pganalyze as a side project before going full-time. His secret to reaching 7-figure ARR without funding or a sales team? SaaS content marketing that developers actually trusted. In this episode, Lukas reveals how deep technical blog posts, a weekly YouTube series, and webinars that attracted 400 live attendees became the inbound marketing SaaS engine behind 5...
Enterprise SaaS: How Check Raised $119M With 200 Clients 02.11.2023 45:44
Andrew Brown sold his first startup to Google - and felt empty. He spent three years searching for an enterprise SaaS business he would never want to sell. He found it in SaaS partnerships with platform companies desperate to add payroll but unable to build it themselves. In this episode, Andrew reveals how Check built an enterprise SaaS model targeting just a few hundred platform partners, raised...
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