The SaaS Podcast: How B2B SaaS & AI Founders Get Customers

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 between $1M and $2M ARR with 9% month-over-month growth. His enterprise sales playbook targets CFOs at agencies with 50-200 employees through B2B SaaS sales cold email with an 86-day average cycle.

COR's shift from SMB to enterprise SaaS transformed their metrics: 114% net revenue retention and just 4.5% annual dollar churn. Santi's B2B sales process proves that customizing the demo - not the product - closes enterprise sales deals faster.

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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. He explains why the freemium SaaS approach - combined with one focused SEO project - replaced every other channel they tried, including handwritten letters in the mail. The freemium model unlocked free trial conversion at scale.

Skedda replaced confusing pricing tiers with a generous SaaS free tier plus one $49 paid plan. That simplicity, combined with vertical-specific landing pages for SEO, created a freemium SaaS flywheel where word of mouth matched organic search as a growth driver.

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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 SaaS journey that took them from losing every user when they introduced pricing to landing 500 customers and a pre-seed round from Jason Calacanis' LAUNCH accelerator. Their SaaS fundraising success came from traction, not pitch decks.

Krepling's startup funding story proves that raising from VCs requires real customer traction. The brothers reached 500 paying customers and $1 billion in platform GMV before any investor took them seriously - overcoming the skepticism of being teen founders from Malta.

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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 including Nike, CNN, and Lyft. In this episode, Ryan shares the startup traction playbook he wishes he had - from launching free to get early traction, to SEO and review sites as growth engines, to the pricing mistake that cost him five years of revenue.

Ryan's getting traction journey proves that initial traction comes from launching free online rather than in-person pilots. His biggest regret: 70% of Humanity's customers generated only 10% of revenue because he lacked the confidence to charge more for five years.

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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 charging more actually improved retention, and how she grew the company to 60 employees and $28 million in funding by competing against free Google Analytics. Her pricing strategy evolved through painful lessons about pricing optimization.

Oribi founder Iris Shoor raised SaaS pricing from $79 to $500/month and discovered that customers with real marketing budgets invested more in the product, extracted more value, and churned less. Her pricing model proved that competing against free requires demonstrating clear ROI, not matching their price.

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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 white-labeled analytics inside other SaaS products. Their competitive differentiation comes from querying data where it already lives instead of moving it. Zandra's SaaS sales strategy combines creative outbound with sharp SaaS differentiation.

From handwritten letters to fish-and-chip demos to LinkedIn messages citing podcast quotes, Zandra proves that standing out in SaaS requires a sales approach as distinctive as your product. Her SaaS sales strategy narrowed from "all software vendors" to four verticals on AWS using the Crossing the Chasm framework.

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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 VC world, and how product-led growth can sell a SaaS onboarding tool without a sales team. Userflow's self-serve SaaS approach means many customers complete a free trial and purchase without a single conversation.

Esben's PLG strategy is built on exceptional UX and treating every support ticket as a product improvement opportunity. This product-led growth mindset lets 2 people serve hundreds of paying customers without dedicated support staff.

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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 SaaS leasing platform after brand partners kept asking for access to renters at the point of move-in. That shift to vertical SaaS, combined with an ML-powered tenant screening engine, helped Findigs reach $2M ARR with just 12 people serving 60,000 units.

Carroll's journey from consumer payments to industry-specific SaaS proves that the best niche SaaS ideas come from listening to adjacent stakeholders, not just your core users. Findigs differentiated in a crowded vertical software market by integrating alongside existing tools instead of replacing them.

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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 startup funding round of 1.2 million pounds. The twist? Holly didn't raise capital by pitching VCs with a deck. Her pre-seed funding came from relationships she built by asking for advice, not money. And she grew to 60,000 users spending almost nothing on paid marketing.

Holly's SaaS fundraising journey proves that raising capital works better when investors see genuine traction. Her pre-seed investors all offered to invest after being asked for advice, not money - and LinkedIn content drove growth without a marketing budget.

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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 month, serves customers like T-Mobile and Apple, and generates multi-million dollar revenue - all bootstrapped with a team of 15. But Ben admits his SaaS monetization mistakes cost him millions by not adding enterprise pricing sooner.

Ben's SaaS pricing evolution went from free to $50 self-serve to custom enterprise deals. His monetization strategy finally clicked when he stopped dismissing sales calls and learned that enterprise buyers have entirely different expectations around billing, support, and contracts.

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