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
SaaS Sales Strategy: 7 Steps From $2K to $100K Deals 15.12.2022 57:51
Khadim Batti had 40 customers and thought he had product-market fit. Then the churn started and the SaaS sales strategy stalled. The real problem was not the product - it was seven SaaS go-to-market gaps that needed fixing sequentially. If your SaaS sales strategy is not converting, this episode walks through every step Whatfix took to go from $2,000 annual deals to $100K+ enterprise sales contrac...
Selling SaaS Without Sales Experience to a $20M Series A 08.12.2022 43:44
Nik Mijic had never sold anything in his life. As a former program manager at LinkedIn, selling SaaS without sales experience was the last skill he expected to need. But he figured it out - landing 20 first SaaS customers through his network and raising a $20 million Series A from Andreessen Horowitz. If you are a technical founder selling SaaS without sales experience, this episode is your playbo...
Niche SaaS: 90% Adoption and 100% Renewal to $2M ARR 01.12.2022 49:04
April LaMon started a niche SaaS in one of the most unlikely markets - mobile apps for master-planned residential communities. One pilot project hit 90% adoption in 90 days and turned into a bootstrapped business doing $2M ARR with a 100% renewal rate. If you are building a niche SaaS or exploring vertical markets, this episode shows how white-labeling, multi-year contracts, and land-and-expand se...
SaaS Product Validation: $1M ARR After Zero Research 24.11.2022 52:39
Hung Dang spent a full year building Y42 without any SaaS product validation - no customer interviews, no feedback, no research. When he finally launched, 30% of what customers needed was missing and 20% of what he built was unnecessary. But through founder-led sales and vision selling, Y42 still hit $1M ARR in its first year on the market. In this episode, Hung reveals how his door-to-door fundra...
Bootstrapped SaaS Growth: $700K and 5 Years to $5M ARR 17.11.2022 40:12
Jason Bergenske invested $700,000 and five years building vertical SaaS software before he got a single paying customer. He funded the entire thing from his family's moving company - no venture capital, no outside investors. This is a story of bootstrapped SaaS growth powered by domain expertise and pure conviction. In this episode, Jason reveals how a frustration with pen-and-paper operations led...
SaaS Pricing Pivot: Micropayments to $80M ARR Platform 10.11.2022 45:54
Trevor Kaufman sold his house to keep his startup alive. He had 100 meetings with media companies and barely closed a deal. Most told him digital content should be free. But Trevor's SaaS pricing pivot from micropayments to flat subscriptions changed everything. In this episode, Trevor reveals how Piano went from a two-person micropayment company to an $80M ARR vertical SaaS platform with 800 cust...
Startup Funding: He Got Customers to Call VCs For Him 03.11.2022 58:57
Jeremy King had no product, no revenue, and a six-month deadline from his wife. Instead of pitching VCs the usual way, he convinced 15 potential customers to call investors and ask them to fund Attest so they could buy the product. That startup funding hack compressed two years of struggle into four months. In this episode, Jeremy reveals how he used Series B investors to create warm intros to see...
Sales Pipeline: Why Paddle's Upmarket Push Failed First 27.10.2022 1:04:59
Christian Owens hired a team of senior enterprise sales reps at Paddle and watched them all quit within nine months. The sales pipeline had value - customers doing $50M in annual volume were already on the platform. But scaling SaaS to enterprise requires a completely different value proposition, and the team was still selling the one built for $1M companies. In this episode, Christian reveals how...
SaaS Sales Process: 80 Doctors to 1,000 Customers 20.10.2022 59:38
Zak Holdsworth built a vertical SaaS company in a market so small that early prospects could count every potential customer on two hands. Then he personally guaranteed their payroll to close the deal. His SaaS sales process was unconventional, but it worked. In this episode, Zak reveals how Hint Health went from 80 direct primary care doctors to nearly 1,000 customers processing over half a billio...
B2B SaaS Sales: Basement Startup to $300M ARR 13.10.2022 41:29
In 2010, Doug Winter and his co-founders started building Seismic in a basement in San Diego. They had no venture funding, no brand recognition, and no product category to sell into. Despite that, they targeted B2B SaaS sales to large enterprises from the very first deal. Twelve years later, Seismic hit $300M in ARR, grew to 1,500 employees and 2,500 customers, and raised $450 million. In this epi...
Freemium SaaS: How a Free Product Led to a $200M Exit 06.10.2022 57:26
Patrick Campbell cashed out his 401k and gave himself nine months to build a company. Ten years later, Paddle acquired ProfitWell for $200 million - one of the largest bootstrapped SaaS exits in recent history. The foundation was a freemium SaaS model that competitors could not match. In this episode, Patrick reveals why he made his analytics product free while competitors raised millions, how acc...
SaaS Onboarding: User Stories That Ship Better Products 29.09.2022 51:39
Most SaaS teams skip user stories and jump straight to building. Then they spend months fixing features nobody asked for. Matt Genovese has spent 27 years in product development and says SaaS user stories are the cheapest insurance against wasted development time. In this episode, Matt breaks down his exact framework for writing user stories that keep teams aligned and reveal hidden feature gaps b...
Niche SaaS: Why 3 Verticals Nearly Killed His Company 11.08.2022 42:53
Stefan Laven knew sports was the right niche SaaS market for Data Talks from day one. But he picked three verticals anyway because one felt too risky. That decision cost years of growth, scattered his team, and diluted his product. In this episode, Stefan reveals how Data Talks went from struggling across sports, retail, and utilities to hitting $250K MRR with 500 customers after finally committin...
Selling a SaaS Business: Shopify App to 7-Figure Exit 04.08.2022 55:29
In 2016, Ryan Kulp made a SaaS acquisition that changed his career. He bought a tiny Shopify app called Notify with a few hundred customers and turned it into FOMO - a social proof platform used on over 30,000 websites generating seven figures in annual revenue. Six years later, he completed the journey by selling a SaaS business to Relay Commerce. The playbook was unconventional. Cold emails usin...
SaaS SEO Strategy: 2 Visitors to 3M Monthly Organic 21.07.2022 50:09
Farzad Rashidi's marketing team at Visme spent months creating content and got two website visitors - one was his mom. Then he flipped the SaaS SEO strategy playbook: 80% promotion, 20% creation. That SaaS content marketing approach grew Visme to 3 million monthly organic visitors and 14 million active users. Along the way, the internal link-building tool became Respona - but selling it as a stand...
Early Traction: 499 Customers in One Day on Product Hunt 14.07.2022 47:13
Vedran Rasic launched LeadDelta on Product Hunt and signed up 499 customers in a single day. It was the second time he won #1 Product of the Day - and it all came down to an early traction strategy he has repeated across multiple products. In this episode, Vedran breaks down his exact Product Hunt launch playbook for SaaS go-to-market success. You will learn the pre-campaign preparation that matte...
SaaS Subscription Billing: Free 18 Months, Then $2.4M 24.06.2022 45:19
Cristina Vila spent 18 months giving Cledara away for free. She had no SaaS subscription billing system, no pricing plan, and activation was stuck at 50%. Then she started charging - and everything changed. When Cledara introduced its first paid plans, activation jumped to 80% because paying customers felt compelled to actually use the product. A year later, Cristina raised SaaS pricing again with...
Enterprise SaaS: 6 Months With No Code, Then Revenue 16.06.2022 46:44
Thor Olof Philogene spent six months validating Stravito's enterprise SaaS opportunity with nothing but slide decks - no code, no product, no revenue. Then he entered a competitive bid against legacy vendors and had to build the product while proving it every two weeks. In this episode, Thor reveals how Stravito landed Fortune 2000 customers like Comcast, Electrolux, and McDonald's as a tiny start...
Self-Serve SaaS: 7-Figure ARR With Just 3 People 03.06.2022 50:41
After raising $37 million and building a 200-person team at his previous startup, Esben Friis-Jensen chose a radically different path with Userflow. He built a self-serve SaaS model and scaled to multiple 7-figure ARR with just three people. In this episode, Esben reveals how Userflow competes against 20+ rivals through product-led growth, why spending 50% of development time on UX fixes is their...
SaaS Content Strategy: $15K MRR to $2.5M ARR 27.05.2022 43:56
Josh Haynam spent six years bootstrapping Interact to $1M ARR using nothing but a SaaS content strategy built on niche technical guides. Then the pandemic supercharged growth - and then killed it. Revenue flatlined at $2.4M for an entire year. In this episode, Josh reveals how Interact broke through a year-long revenue plateau by rebuilding onboarding, launching quiz templates that doubled as an a...
SaaS SEO Strategy: $50/Month to 8-Figure ARR 13.05.2022 46:57
Tony Summerville started charging $50 a month for fleet management software. One customer thought that meant $75 per vehicle and still said yes. That pricing gap was the first signal his SaaS SEO strategy would drive 4,000 customers. Learn how Tony built a SaaS SEO strategy that drives 70% of revenue through inbound marketing SaaS methods, ranking #1 for 'fleet software' with SaaS content marketin...
SaaS Customer Discovery: 400 Calls to $25K MRR 05.05.2022 58:27
Gary Vanbutsele spent 18 months building a product nobody paid for. His second attempt at SaaS customer discovery worked - he pre-sold to 5 customers at $5K each. Then SaaS partnerships delivered the real breakthrough. Learn how Gary ran SaaS customer discovery by contacting 400 consultants for SaaS partnerships, converting 10 into active partners who drove partner-led growth delivering 120 custom...
Enterprise Sales: 7 Years Bootstrapped to $100M ARR 21.04.2022 49:33
Alfonso de la Nuez spent six years running usability tests in a Spanish lab before building an enterprise sales engine. His consultancy to SaaS journey reached nearly $100M ARR in enterprise SaaS. Learn how UserZoom used enterprise sales hustle to land Google and eBay, bootstrapped to $15M before raising $34M for enterprise growth, and how Thoma Bravo valued the business at $800M. Alfonso is the c...
Bootstrap to Profitability: $60K Lost, Then the Fix 08.04.2022 55:46
Dave Rodenbaugh lost $60K on a failed SaaS acquisition and $50K building a help desk nobody wanted. Then he acquired Recapture at $3,500 MRR and found the bootstrap to profitability formula. Learn the 3-criteria checklist for buying SaaS businesses that achieve bootstrap to profitability, why dropping prices from $49 to $29 unlocked Shopify growth, and how a solo founder SaaS can scale through par...
Net Revenue Retention: CAC, LTV, and Churn Explained 25.03.2022 53:38
Most SaaS founders get their SaaS metrics wrong. Paul Orlando says if you have one number for CAC and one for LTV, you haven't started measuring net revenue retention properly. Learn how to calculate customer acquisition cost by channel, model LTV as a river, track net revenue retention by cohort, and why negative SaaS churn is the gold standard. Paul is a USC professor and author of Growth Units....
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