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

By Omer KhanBusiness Entrepreneurship Technology

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

January 22First Customers: He Lived in His Customer's Basement
He wore a Stanford sweatshirt to a conference. Five minutes later, he had his first customer. Nate Baker found his first customers through network selling, not cold outreach - then lived in that customer's basement for a year. That relationship set the foundation for Qualia's growth to $100M ARR.
Nate reveals why the first 25 Qualia employees rotated through Barry's basement to learn the industry, the multi-year upfront contracts that brought forward $100K in cash at just $45K ARR, and the wake-up call when a VP of Sales said: "I've never seen such a gap between great product and incompetent sales execution."
Qualia is a title software platform generating over $100M in ARR with 600 employees and $200M+ raised. Nate started building at 21 with zero real estate experience and found his early customers entirely through network-based relationships.
This episode is brought to you by:
💖 Gearheart → Book a free consult and get the first 20 hours free
🔑 Key Lessons
🤝 First customers must come from network selling: Nate says your first 10 customers have to be in-network sales. Barry introduced Qualia to his competitors, building the foundation for initial traction.
🏠 Embed yourself with first customers to learn their world: Nate and the first 25 Qualia employees rotated through living in Barry's basement. "To actually understand what your customer does, you just have to be so in it."
💰 Use multi-year upfront contracts to align early incentives: Qualia offered 5-year contracts at 80% discounts, collecting $100K upfront from early customers when they had just $45K ARR.
🗺️ Geographic focus beats national expansion for first customers: Qualia stayed in Massachusetts for the first year, building density and network effects in one state before expanding.
🔧 Hire sales leadership before you think you're ready: At $45K ARR, Qualia's VP of Sales exposed the gap between great product and incompetent execution. Within 12 months they hit $3.5M ARR.
Chapters
Introduction and what Qualia does
How Nate picked the title software market at 21
Finding first customer Barry Feingold at a conference
Living in Barry's basement for a year
When Barry's vendor shut him off overnight
Why narrow geographic focus beats national expansion
How to get first customers to pay before building
The multi-year upfront contract strategy
Network selling vs cold outreach for first customers
The wake-up call: "Great product, incompetent execution"
Moving upmarket and geographic expansion
How AI is changing the opportunity
Lightning round
Resources
Full show notes: https://saasclub.io/467
Join 5,000+ SaaS founders: https://saasclub.io/email
49 min
January 15B2B SaaS Sales: A Cold Text That Landed McDonald's
A cold text to a stranger's phone number. Nine months just to close the POC paperwork. Yosef Peterseil landed McDonald's as his first B2B SaaS sales customer while bootstrapping with zero revenue. The lesson: charging even $3,000 for a POC completely changes the dynamics of closing deals.
Yosef reveals why their original ICP of customer success managers had no budget, how 70 hard-earned event leads went cold because they had no follow-up system, and the 13-month contract structure that eliminated double-negotiation traps in B2B deal cycles.
Blings is a personalized video platform serving enterprise sales customers including McDonald's, Mercedes, Meta, and Rocket Mortgage. The company hit $1M ARR in 2023 with a team of 19.
This episode is brought to you by:
💖 Gearheart → Book a free consult and get the first 20 hours free
🔑 Key Lessons
🎯 Validate ICP budget before building your B2B SaaS sales motion: Yosef interviewed dozens of customer success managers before discovering they had no budget - pivoting to marketing where the money was saved months of wasted effort.
💰 Always charge for POCs in B2B SaaS sales: Even $3,000-$5,000 forces customers to prioritize your project, starts vendor onboarding, and signals they're serious about closing deals rather than just exploring.
📄 Combine POC and commercial into one contract: Yosef lost months negotiating POC terms only to negotiate again for the commercial deal - 13-month contracts with first-month exit clauses eliminated the trap.
📉 Build follow-up systems before generating leads: Blings spent $20K-$30K on a conference and captured 70 leads, but had no lead scoring or sequences - the entire investment was wasted.
🔗 Use channel partners to scale enterprise sales doors: Recruiting industry veterans to open doors for recurring commission scaled Blings faster than direct B2B SaaS sales alone.
Chapters
Introduction and favorite quote
What Blings does - the MP5 video format
Company metrics and enterprise customers
Validating the ICP through customer interviews
Pivoting from customer success to marketing
Landing McDonald's through a cold text
Closing the first B2B SaaS sales POC
Why you should always charge for POCs
Event marketing mistakes - 70 lost leads
Hiring salespeople too early
Building channel partner relationships
Lightning round
Resources
Full show notes: https://saasclub.io/466
Join 5,000+ SaaS founders: https://saasclub.io/email
43 min
December 11, 2025Enterprise Sales: How to Close Deals in 9 Days
Most founders think enterprise sales takes 6-12 months. Bassem Hamdy closes deals in 9 days. After scaling Procore from $10M to $100M, Bassem built Briq - an AI workforce platform now doing 8 figures in revenue. His enterprise sales strategy is counterintuitive: never demo the product early, never do free POCs, and always charge from day one.
Bassem reveals why selling to enterprise starts with vision and value before showing a single screen ("I could demo a blank screen - they don't know what you're demoing anyway"), how targeting CFOs instead of innovation teams compresses B2B sales cycles, and the land-and-expand playbook that grew a $15K first deal into 8-figure enterprise sales revenue.
Briq is an AI orchestration platform for construction and manufacturing that automates back-office work for enterprise deal cycles across Fortune 100 companies. Bassem spent 15 years in construction tech before selling to enterprise in this market.
This episode is brought to you by:
💖 Gearheart → Book a free consult and get the first 20 hours free
🔑 Key Lessons
🏢 Enterprise sales starts with vision, not demos: Bassem says "I could demo a blank screen" - customers don't know what they're looking at anyway. Align on vision and value first, and enterprise deal cycles shrink from months to days.
💰 Never do free POCs in enterprise sales - even $1 creates commitment: Free pilots attract time-wasters. The moment money changes hands in B2B sales, prospects become invested in making the product work.
🎯 Target CFOs, not innovation teams: Innovation teams chase shiny objects but can't write checks. CFOs control the checkbook, love price certainty, and close enterprise sales quickly once they see ROI.
📈 Land small and expand to grow revenue: Briq's first deal was $15K. Through disciplined land-and-expand with consumption pricing, they grew to 8 figures selling to enterprise.
🔄 Don't pivot away from product-market fit: Briq had PMF with their automation product but pivoted to forecasting under investor pressure - and had to "refound" the company to recover.
Chapters
Why SaaS founders should ignore feature requests
Introduction and welcome
What Briq does: AI workforce for physical industries
The failed "construction data cloud" idea
The investor-forced pivot to forecasting
How to close enterprise sales deals in 9 days
Selling on vision and value vs. features
Why you should never do free enterprise POCs
SaaS pricing: moving to consumption-based tokenization
Selling to CFOs: overcoming risk aversion
Firing bad enterprise clients
Lightning round
Resources
Full show notes: https://saasclub.io/465
Join 5,000+ SaaS founders: https://saasclub.io/email
47 min
December 04, 2025Consultative Selling: How He Closed Instacart Live
His co-founder live-coded a fix during the Instacart pitch - and closed the deal on the spot. Saket Saurabh used consultative selling SaaS techniques to close 15 enterprise customers including Instacart, LinkedIn, and DoorDash before hiring a single salesperson.
Saket reveals why he went "enterprise first" instead of starting with SMBs, the consultative selling SaaS approach that turns every meeting into problem-solving instead of pitching, and the zero-salary pivot that made Nexla cash flow positive before their $12M Series A.
Nexla is an enterprise data platform serving 50+ customers with 6-figure ACV deals. Saket's founder-led sales motion grew the company to over $5M ARR after raising $33M total.
This episode is brought to you by:
💖 Gearheart → Book a free consult and get the first 20 hours free
🚨 NordStellar → Book a demo and get 20% off with code blackfriday20
🔑 Key Lessons
🤝 Consultative selling SaaS connects product to market: Unless founders sell deals themselves, they miss critical signals about pricing and product direction. Saket closed 15 enterprise customers before hiring salespeople.
🪄 Create "magical moments" in demos: Saket's co-founder live-coded a data fix during the Instacart CTO pitch, solving in minutes what took their team weeks. Enterprise selling with agility closes deals faster than slides.
🏢 Go enterprise first to build for real complexity: Architecting for SMBs first prevents you from understanding enterprise-grade problems. Nexla targeted Fortune 500 companies from day one.
🎯 Use thesis-driven outreach instead of cold pitching: Saket built specific hypotheses about each target company's data problems. Starting with "Do you see this problem?" earned trust with technical buyers.
💰 Price against internal build cost, not competitors: Saket estimated what the prospect would spend on internal engineering, then priced Nexla at one-fifth to one-tenth. Consultative selling SaaS means understanding the buyer's economics.
Chapters
Introduction - the "magical moment" at Instacart
What is Nexla? Solving enterprise data fragmentation
Origin story: from Nvidia engineer to data entrepreneur
Why target enterprise customers from day one
What a typical consultative selling meeting looked like
The live-coding demo that closed Instacart
Figuring out enterprise pricing
Closing 15 enterprise deals through founder-led sales
Overcoming the "we can build it ourselves" objection
The zero-salary pivot to cash flow positivity
How AI changed Nexla's product and market
Lightning round
Resources
Full show notes: https://saasclub.io/464
Join 5,000+ SaaS founders: https://saasclub.io/email
40 min
November 27, 2025AI SaaS: Escaping the Consulting Trap to Hit $1M ARR
$150K ARR. Customers never logged in. They'd call with a question, get an answer, and disappear. Ibby Syed spent 18 months building what he thought was an AI SaaS - then realized he'd accidentally built a consulting business. The wake-up call came when 100 lines of OpenAI code replaced his entire data science solution.
Ibby reveals the exact moment that triggered the AI SaaS pivot, why teaching customers to build their own AI agents scales better than building for them, and the outbound strategy where he sends actual leads from Reddit monitoring before the first call.
Cotera is an AI-powered platform that lets enterprise customers build prompt-based AI agents on top of their existing data warehouses. The AI startup has 15 enterprise customers and generates over $1M ARR with a team of 10.
This episode is brought to you by:
💖 Gearheart → Book a free consult and get the first 20 hours free
🚨 NordStellar → Book a demo and get 20% off with code blackfriday20
🔑 Key Lessons
🚨 Recognize when your AI SaaS is actually consulting: Ibby hit $150K ARR but customers weren't logging in. They called for answers instead of using the product - a dangerous signal he almost ignored.
💡 Let API breakthroughs trigger your pivot: Ibby's co-founder solved a customer problem with 100 lines of OpenAI code that outperformed a complex data science solution. That contrast made the AI startup opportunity obvious.
🎯 Deliver value upfront in outbound: Instead of pitching, Ibby sends actual leads from a Reddit monitoring AI agent. Showing value before the first call converts better than any cold pitch.
🛠️ Teach customers to build, don't build for them: After the pivot, Cotera stopped doing custom implementations. Teaching customers to build their own AI agents is what made the AI SaaS business scale.
🏢 Enterprise customers want AI on their own infrastructure: Series B+ companies want AI-powered platform capabilities on their existing Snowflake or BigQuery, not third-party clouds.
Chapters
Introduction and the "White Collar" quote
The Y Combinator journey and the first idea
Getting first customers through LinkedIn outbound
The consulting trap - revenue vs. scalability
The wake-up call - 100 lines of code vs. data science
The pivot to building an AI SaaS agent platform
The "teach, don't do" service model
Prompt-based workflows vs. drag-and-drop
Why vertical AI startups might die
Making AI agents work at scale
Lightning round
Resources
Full show notes: https://saasclub.io/463
Join 5,000+ SaaS founders: https://saasclub.io/email
55 min
November 20, 2025Freemium SaaS: Millions of Users to 7-Figure ARR
First paying customer: $8 a month for a fantasy football league. Bilal Aijazi's freemium SaaS grew to millions of monthly active users and 7-figure ARR with just 20 people. The challenge was figuring out which of those millions would actually pay.
Bilal reveals how he separated casual free users from real buyers in a freemium SaaS, the viral loop where 12% of responders become creators who send polls to new groups, and why diversifying to Teams, Zoom, and Google Slides saved Polly when Slack built a competing feature.
Plus: the product-led growth insight that "pollinators" - users picking lunch spots who will never pay - actually drive awareness for the enterprise buyers running company all-hands.
Polly is a freemium SaaS engagement platform serving millions of monthly active users across Slack, Teams, Zoom, and embedded presentation tools. The free-to-paid conversion engine generates multiple seven figures in ARR with a team of 20.
This episode is brought to you by:
💖 Gearheart → Book a free consult and get the first 20 hours free
🚨 NordStellar → Book a demo and get 20% off with code blackfriday20
📡 Signal House → Learn more and get a demo
🔑 Key Lessons
🚀 Launch on platforms before the ecosystem matures: Polly launched on Slack before an app store existed. 80% of users completed a painful 5-step install, proving early movers on viral platforms get compounding distribution.
💰 Separate users from buyers in a freemium SaaS: Most free users picking lunch spots will never pay. The real buyers are comms leaders running company all-hands and sales kickoffs worth 150+ person-hours.
🔄 Build viral loops into the freemium SaaS product: 12% of Polly responders become creators, who send polls to new groups where another 12% convert. This compounding freemium conversion loop drives growth without paid acquisition.
🏢 Diversify across platforms before risk becomes existential: When Slack built Workflow Builder to compete, Bilal had already expanded to Teams, Zoom, and Google Slides.
🧠 Creator pricing beats workspace pricing for horizontal products: Charging only poll creators avoids monetizing casual users who churn. Enterprise tiers shift to monthly active users for simpler administration.
Chapters
Introduction
What Polly does and who it serves
Origin story - messaging platforms meet enterprise
Launching on Slack before the app store existed
Product Hunt viral moment and early growth
The freemium SaaS monetization strategy
First paying customer - $8/month fantasy football league
Separating users from buyers in a horizontal product
Free-to-paid conversion challenges
When Slack built a competing Workflow Builder feature
Building across multiple platforms today
Lightning round
Resources
Full show notes: https://saasclub.io/462
Join 5,000+ SaaS founders: https://saasclub.io/email
55 min
November 13, 2025Bootstrapped SaaS to 8-Figure Exit With No VC Funding
4,000 pound WordPress plugin. No tech skills. No VC funding. 8-figure exit. James Ashford built GoProposal as a bootstrapped SaaS for accountants and sold it to Sage - proving you don't need massive funding to build a valuable company.
James reveals the self-funded playbook that took him from business consultant to successful founder, why he printed acquirer logos on his wall before getting his first customer, and the "market like a celebrity chef" strategy that let him dominate online when COVID killed competitor events.
GoProposal is a bootstrapped SaaS proposal and pricing platform for accountants that reached 1.5M ARR with 1,100+ customers, a 78 NPS score, and just 12 people before the 8-figure exit to Sage. A profitable SaaS from day one.
This episode is brought to you by:
💖 Gearheart → Book a free consult and get the first 20 hours free
📡 Signal House → Learn more and get a demo
🚨 NordStellar → Book a demo and get 20% off with code blackfriday20
🔑 Key Lessons
🚀 A bootstrapped SaaS MVP doesn't need perfect tech: James built GoProposal on a 4,000 pound WordPress plugin that scaled to 1,100+ customers and an 8-figure exit - solving a real problem matters more than sophisticated technology.
🎯 Build your bootstrapped SaaS to sell from day one: Before his first customer, James calculated his freedom number and printed potential acquirer logos on his wall. Every business decision was made with the exit in mind.
🤝 Buy credibility strategically as an industry outsider: James traded 10% of GoProposal for 10% of a respected accounting firm, giving instant insider status and the ability to speak from multiple perspectives.
📚 Market like a celebrity chef - give away your methodology: Gordon Ramsay shares recipes for free, yet people eat at his restaurants. James gave away his entire pricing framework and people still bought the software.
💰 Bootstrap constraints force better strategies than funding: When conferences cost 25K, he hired a full-time videographer instead. When COVID hit, competitors lost events while GoProposal dominated online.
Chapters
The "Don't Wish It Were Easier" philosophy
What GoProposal does for accountants
From business consultant to bootstrapped SaaS founder
The 4,000 pound WordPress MVP that scaled
Trading equity for credibility
Writing a bestselling book in 2 weeks
Getting the first 100 customers
The bootstrapped SaaS marketing playbook
The PATH Method: Pain, Aspirations, Traps, How
Onboarding: the shock and awe approach
Why he skipped conferences for a videographer
Preparing for exit from day one
The M&A process and due diligence
Lightning round
Resources
Full show notes: https://saasclub.io/461
Join 5,000+ SaaS founders: https://saasclub.io/email
1 hr 14 min
November 06, 2025SaaS Pricing: Zero Revenue From One Costly Mistake
Usage-based SaaS pricing with no minimums. Customers could scale to zero without leaving. Ryan Wang launched Assembled with a pricing model that let revenue drop to nothing during COVID - even though no one was churning. It took 8 months to earn his first dollar.
Ryan reveals the SaaS pricing fix that turned zero revenue into 8-figure ARR, why his team blamed themselves for months before realizing the usage-based pricing problem was macro-driven, and the pricing strategy of adding minimums and building sticky features that prevented future revenue collapses.
Assembled is an AI platform for customer support that helps companies manage both human and AI agents. Ryan previously worked as a machine learning engineer at Stripe. The company now generates tens of millions in ARR.
This episode is brought to you by:
💖 Sprinto → Book a demo and get 10% off + your first pentest FREE
💖 Gearheart → Book a free consult and get the first 20 hours free
📡 Signal House → Get featured on 150+ podcasts in your niche
🚨 NordStellar → Book a demo and get 20% off
🔑 Key Lessons
💰 SaaS pricing needs minimums to survive downturns: Assembled's pricing model with no minimums let customers scale to zero during COVID, dropping revenue to nothing for 8 months and proving that pricing floors are essential.
🎯 Universal pain points reveal product-market fit: Ryan found PMF when every support leader showed the same messy color-coded spreadsheet for scheduling - proving the problem generalized across companies.
⏳ Plant seeds when there is no harvest in sight: Assembled went 8 months with zero revenue, but Ryan kept meeting customers in person and building around their needs, creating the foundation for 8-figure ARR.
🔧 Filter custom deals by what generalizes: Ryan took Robinhood's custom enterprise deal because those features would scale, but walked away from an airline needing Microsoft Dynamics integration.
🤝 Win one community before scaling channels: Ryan focused on the Support Driven Slack community, building trust until every member looking for workforce management was already "team Assembled."
Chapters
Introduction
Seeds vs. harvest: the founder mindset for surviving zero revenue
Founding story: from Stripe ML engineer to Assembled
The workforce management problem explained
Product-market fit: the color-coded spreadsheet discovery
Pandemic launch: TechCrunch and Hacker News on the worst day
SaaS pricing mistake: why usage-based with no minimums failed
The custom deal filter: build vs. walk away
Scaling from 10 to 50 customers with data-driven ICP
Community-led growth: winning Support Driven
Lightning round
Resources
Full show notes: https://saasclub.io/460
Join 5,000+ SaaS founders: https://saasclub.io/email
52 min
October 30, 2025Bootstrapped SaaS: $400K to $30M ARR With Zero Funding
$50 million exit already in the bag. But Sam Darawish chose to bootstrap his next SaaS with just $400K. He didn't pay himself for two years. He showed up to Affiliate Summit with nothing but screenshots. Two people signed up - and became his first customers. Founders will hear how Sam built a bootstrapped SaaS from a tiny niche to nearly $30M ARR without a single dollar of outside funding.
Sam reveals why he deliberately chose a $70M TAM niche for faster capital efficiency, how the self-funded SaaS achieved $250K revenue per employee, and what went wrong when Everflow expanded from affiliate networks to direct brands - a market shift that increased churn and forced a rethink.
Everflow is a bootstrapped SaaS platform for partner marketing, serving 1,200 customers with 120 people across four global offices. Sam previously co-founded Moolah Media, acquired by Opera for $50M, where the bootstrap mindset originated.
This episode is brought to you by:
💖 Sprinto → Learn more and book a demo today
📡 Signal House → Learn more and get a demo
🚀 SaaS Club Launch → Build your SaaS to $10K MRR
🔑 Key Lessons
💰 Capital scarcity forces bootstrapped SaaS focus: With only $400K and a few engineers, Sam built only essential features and optimized cloud costs from day one - the foundation of capital efficiency.
🎯 Validate with screenshots, not products: Sam rented a booth at Affiliate Summit before having working software. Most people walked away, but two became his first customers.
📉 Adjacent markets can have hidden friction: Everflow's self-funded SaaS worked great for affiliate networks but struggled with direct brands - under-resourced teams of 1-2 people needed more automation.
🚀 Small TAM can accelerate early bootstrapped SaaS growth: Sam deliberately chose mobile affiliate networks ($70M TAM) over the larger market because knowing the niche deeply helped reach $1M ARR faster.
🧠 Moderate growth preserves bootstrap discipline: Growing 25-30% yearly instead of chasing hypergrowth prevents taking on customers outside your ICP and keeps the company profitable.
Chapters
Introduction
What is Everflow?
Business snapshot - $30M ARR, 1200 customers
Bootstrapping and self-funding
Moolah Media origin and $50M Opera acquisition
How the Everflow idea was validated
Why $400K not $4M - capital efficiency philosophy
Defining first ICP - mobile affiliate networks
First customers at Affiliate Summit with screenshots
Reaching $1M ARR with 10 people
Expanding beyond the niche to direct brands
Capital efficiency vs hypergrowth
Lightning round
Resources
Full show notes: https://saasclub.io/459
Join 5,000+ SaaS founders: https://saasclub.io/email
43 min
October 23, 2025Product-Led Growth: 8-Figure ARR With $0 Ad Spend
$200M exit. CEO of Foursquare. Then David Shim bet everything on product-led growth with zero ad spend. The first version flopped - just 5% of users came back after 30 days. But instead of hiring a sales team, David doubled down on making the product so valuable that people couldn't stop sharing it. Today, Read AI adds 12 million accounts per year through product-led growth alone.
David reveals how auto-sharing meeting notes turned every meeting into a viral distribution channel, why he built a multimodal "narration layer" that captures tone and emotions transcripts miss, and how Read AI landed Fortune 500 customers through self-serve growth without salespeople for three years.
Read AI is a meeting intelligence platform that has grown to 8-figure ARR with nearly zero marketing spend. David's PLG playbook turned product virality into the company's primary growth engine.
This episode is brought to you by:
💖 ⁠⁠Sprinto⁠⁠ → ⁠⁠Learn more and book a demo today
🚀 SaaS Club Launch → Build your SaaS to $10K MRR
🔑 Key Lessons
🚀 Build product-led growth into the product itself: Read AI auto-shares meeting notes with all participants, turning every meeting into a viral distribution channel that drives 12 million new signups yearly without marketing spend.
📉 Retention reveals product-market fit faster than acquisition: Read AI had strong signups but only 5% monthly retention - proving that growth without retention is just expensive churn.
🎯 Validate by asking incumbents directly: David cold-emailed Zoom's founder to confirm they weren't building what he wanted to create - getting validation from the platform owner before building anything.
💡 Build decision-making tools, not dashboards: The PLG pivot from showing metrics to providing actionable recommendations drove retention from 5% to 81%.
🏢 Let enterprise customers self-serve: Read AI had no salespeople for three years. Fortune 500 companies adopted the product-led growth engine organically and then reached out to set up corporate accounts.
Chapters
Introduction and the $200M Placed acquisition
The ESPN glasses moment - origin of Read AI
Validating by cold-emailing Zoom's founder
Why the first product failed (5% retention)
Building the "narration layer" for differentiation
Retention journey: 5% to 81%
Why product-led growth beat hiring salespeople
Viral loops: sharing reports as the default
Self-serve growth and enterprise conversion
Competing with Microsoft, Google, and Zoom
The future of AI agents
Lightning round
Resources
Full show notes: https://saasclub.io/458
Join 5,000+ SaaS founders: https://saasclub.io/email
54 min

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

From the publisher's feed

Building software got easier. Getting customers didn't. Every week, a founder building B2B SaaS or an AI product tells you how they got their first customers, and how they kept them: what worked, what didn't, and what they'd do differently.