The SaaS Podcast - Real Lessons on Growing Profitable SaaS

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...

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....

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...

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...

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...

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...

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...

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...

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...

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...

Dover got its first 10 customers without a product, website, or even a company name. For nine months, the three co-founders manually reviewed resumes and conducted interviews for their customers while finding product-market fit the hard way. Then COVID hit. Instead of panicking, the founders made a counterintuitive decision: they stopped selling entirely and focused all their energy on building a...

Most SaaS companies build buyer personas around demographics like job titles, age, and gender - then wonder why those personas collect dust. Adrienne Barnes says this broken approach leads to weak SaaS branding and content that talks about the company instead of the customer. Adrienne is the founder of Best Buyer Persona and has built personas for companies like Monday.com and Stripe. In this epis...

Dean McPherson launched Paperform on AppSumo and sold 3,000 lifetime deals - but every customer paid a one-time price, leaving him with zero recurring revenue. Getting those first SaaS customers was just the beginning of a much harder journey. For over two years, Dean and his wife ran Paperform as a lifestyle business with no marketing, no employees, and no growth strategy. Then he made a hiring d...

SpotDraft tried selling to freelancers - no one would pay. They moved to Fortune 500 companies through a channel partner - but each customer took months to onboard. It took two years to learn that you cannot outsource SaaS product validation. You have to own the customer relationship. SpotDraft co-founder Rohith Salim learned that channel partners block SaaS product-market fit because you never ac...

Michael Kansky priced his SaaS at $20/month because that is what he would personally pay. Competitors charged $200. That SaaS subscription billing mistake haunted LiveHelpNow for years, keeping the business flat at $3M ARR for four straight years despite serving enterprise customers. LiveHelpNow bootstrapped to $3M ARR over 12 years but stalled because SaaS pricing based on the founder's wallet re...

When funded competitors started bidding $100 per click on Google Ads, Michael Cooney's bootstrapped SaaS could not compete on spend. He had to find competitive differentiation to grow WhatConverts to $2M ARR without a single dollar of funding. WhatConverts found competitive differentiation beyond call tracking by selling full lead intelligence when funded rivals were bidding on the obvious keyword...

Vishal Sunak spent nine months cold-emailing nearly 100 general counsels before writing a single line of real code. His SaaS fundraising journey took LinkSquares from a fake Rails prototype to $10M ARR and $21M raised across three rounds. LinkSquares validated demand through 100 cold email interviews, built a Rails prototype with no backend in 100 days, and used that traction to power SaaS fundrai...

Thibaud Clement and his wife built a social media tool as a side project while running an ad agency. Their SaaS content marketing strategy helped Loomly reach $5M ARR and 7,000 customers - with just seven people and no sales team. Loomly grew to $5M ARR at 100% year-over-year by making SaaS content marketing the primary growth engine. Thibaud eliminated the sales team entirely, collected 200+ dail...

Most SaaS founders skip straight to demos and email templates without building the foundational narrative their entire SaaS sales process depends on. Pete Kazanjy, author of Founding Sales, explains why that is backwards and how five sequential steps create the sales narrative everything else cascades from. Pete's SaaS sales process framework has five components: identify the problem through custo...

Pete Kazanjy had zero sales experience when he became his startup's first sales rep. As a product marketer, he had to learn selling SaaS without sales experience from scratch. He built TalentBin to acquisition by Monster, then discovered that 60% of selling activity leadership believed was happening simply was not. Pete went from selling SaaS without sales experience to leading startup sales for 6...

Investors told Advait Shinde the K-12 market had no money and Chromebooks were the wrong bet. Today, GoGuardian serves 18 million students - a third of all K-12 in the US - with $50M+ ARR. The enterprise sales strategy that made it happen relied on channel partners, not outbound teams. GoGuardian grew enterprise sales to $50M+ ARR by pre-incentivizing channel resellers like CDW, who now drive over...

In 2012, Suneera Madhani was selling payment terminals out of her VW Beetle. When she pitched a flat-rate recurring revenue model to her bosses, they laughed in her face. Twelve payment processors rejected her idea. Five years later, Fattmerchant was processing $5B in payments and generating $25M in ARR. Suneera built Fattmerchant to $25M ARR by replacing opaque per-transaction SaaS pricing with a...

When Daniel Scrivner joined Flow as CEO, the company was bleeding 5% of revenue every month. The team had been spending $100K/month on paid ads, but SaaS retention kept declining. With six people, zero ad budget, and no CEO experience, Daniel had to stop the bleeding. Daniel reversed Flow's 5% monthly revenue decline by improving SaaS retention through product redesign, cancellation flow optimizat...

Nine months ago, Sabba Keynejad was doing $10K MRR with VEED.io. They had been rejected by YC and nearly shut down with one month of runway left. Then they figured out a SaaS SEO playbook that changed everything. In less than a year, they grew from $100K to $2.2M ARR - bootstrapped, with no sales team. VEED.io grew from $100K to $2.2M ARR by building standalone tool pages optimized for high-volume...

DocSend was free for three years. When Russ Heddleston added a $10/month plan, conversion went up. When he raised SaaS pricing to $150/month, conversion went up again. Every time DocSend charged more, the product-led growth model performed better. Meanwhile, the outbound sales team had a $19,000 customer acquisition cost - and they shut it all down. DocSend achieved $0 customer acquisition cost by...