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

February 10, 2022SaaS Branding: No Category Name Cost Years of Sales
Benn Stancil built a product customers loved but nobody could name. Mode's SaaS branding fell between BI dashboards and data science tools - a SaaS positioning problem that confused buyers for years.
Learn how Mode solved its SaaS branding challenge by narrowing to 'by analysts, for analysts,' using entertainment-first content for product positioning, and growing to 8-figure ARR.
Benn is the co-founder of Mode, a collaborative analytics platform. Their SaaS branding journey from category creation confusion to clarity serves clients like Lyft, DoorDash, and Bloomberg.
🔑 Key Lessons
🎯 SaaS branding needs a noun buyers can repeat: Mode fell between BI and data science with no category name - a SaaS positioning gap that made sales harder.
📉 Underinvesting in SaaS branding research costs years: Launching without product positioning research led to confused sales conversations for too long.
🛠️ Customers believe your SaaS branding labels: Mode called itself 'collaborative' and buyers repeated it as a purchase reason - despite zero collaboration features.
🚀 Entertainment-first content beats product marketing for SaaS branding: Mode's first blog post analyzed Miley Cyrus data, attracting analysts before they cared about the product.
🧠 Committed decisions beat perfect ones in SaaS branding: Three analytics founders learned that speed outperforms endless hedging on category creation decisions.
Chapters
Introduction
What Mode does and who it serves
Size of the business and key customers
How the idea started at Yammer
SaaS branding challenges after launch
The cost of underinvesting in product positioning
Why finding a category name took years
Handling conflicting customer requests
How SaaS branding language shapes expectations
Acquiring the first 10 customers
Why committed decisions beat perfect decisions
Content marketing and category creation
The startup marathon
Lightning round
Resources
Full show notes: https://saasclub.io/307
Join 5,000+ SaaS founders: https://saasclub.io/email
47 min
February 04, 2022Product-Led Growth: $19/Year Pricing to $1M ARR
AJ started Carrd as a vanity project to pay for lattes. Using product-led growth and freemium SaaS pricing at $19/year, he grew to $100K MRR and 4 million sites with just two people.
Learn how AJ built a product-led growth engine using the freemium model, built-in virality through 'Made with Carrd' links, and a product-led growth approach that replaced all marketing spend.
AJ is the founder of Carrd, a freemium SaaS platform. His product-led growth strategy with bootstrapped SaaS economics let him scale to $1M ARR without a marketing budget.
🔑 Key Lessons
🚀 Product-led growth virality beats paid marketing at scale: Carrd's 'Made with Carrd' link on every free site created a self-sustaining freemium SaaS growth loop.
💰 Keep product-led growth pricing low for maximum revenue: AJ found $19/year with Black Friday discounts drove higher total revenue than raising prices.
🛠️ Invest in product for product-led growth instead of marketing: AJ made more code commits in 2021 than any year, treating product improvement as the primary growth strategy.
🧠 Raise funding for expertise, not capital: AJ raised $2M while profitable to access AWS engineers for a bootstrapped SaaS infrastructure migration.
🎯 Generalize feature requests for your freemium SaaS user base: Virtual sections solved one user's request while unlocking new use cases for everyone.
Chapters
Introduction and what Carrd does
Revenue and product-led growth metrics
Why AJ raised $2M despite being profitable
What drove freemium SaaS growth in 2020
Twitter and building in public
The freemium model and Made with Carrd link
Product-led growth approach over marketing
Lessons on building a great product
Feature requests and product-led growth iteration
Hiring the first developer
Choosing the right investors
Product-led growth pricing and Black Friday conversions
Tech stack and AWS migration
Lightning round
Resources
Full show notes: https://saasclub.io/306
Join 5,000+ SaaS founders: https://saasclub.io/email
51 min
January 27, 2022Startup Funding: 5 Capital Raising Mistakes to Avoid
Brian Parks raised $30M for Bigfoot Capital and has funded 35 B2B SaaS companies. His conclusion: most startup funding fails because founders treat capital raising like a side project instead of a SaaS fundraising priority.
Learn the 5 startup funding mistakes founders repeat and the 8-step process Brian uses on both sides - as someone who manages SaaS fundraising and deploys venture capital SaaS investments.
Brian is the founder of Bigfoot Capital, providing non-dilutive startup funding to B2B SaaS companies at $1.5M-$10M ARR. His capital raising process took 15 months to close $30M.
🔑 Key Lessons
🎯 Treat startup funding like a full-time sales process: Founders who half-commit to capital raising signal weak execution and lose investor trust.
📉 Slow responses destroy startup funding momentum: Brian says time kills deals - speed signals operational competence across the entire business.
🤝 Build an Ideal Capital Provider Profile before startup funding outreach: Target 50 relevant investors, not 1,000 - wrong targeting wastes months on SaaS fundraising.
💰 Run a structured 8-step startup funding process: Brian's framework: discover, acquire, activate, gather results, select, dominate diligence, document, close.
🧠 Negotiate hard at term sheets, not in final docs: Over-optimizing clauses after signing exhausts investors and kills capital raising deals.
Chapters
Introduction
What Bigfoot Capital does
The 5 capital raising mistakes
Mistake 1: The casual startup funding approach
Prep vs. go-to-market in SaaS fundraising
Mistake 2: Shooting from the hip
The 8-step startup funding process
Activate, engage, and follow up
Gather results and term sheets
Dominate diligence
Mistake 3: Wrong audience for capital raising
Mistake 4: Over-optimizing startup funding terms
Mistake 5: Not removing friction
Lightning round
Resources
Full show notes: https://saasclub.io/305
Join 5,000+ SaaS founders: https://saasclub.io/email
37 min
January 20, 2022B2B SaaS Sales: 4 Years to Crack Enterprise Deals
Jody Glidden spent four years solving a CRM data problem before B2B SaaS sales took off. His enterprise sales cycles dragged three years to close a single deal through founder-led selling.
Learn how Introhive cracked B2B SaaS sales by focusing on one vertical, doing founder-led selling for 4 years, and building SaaS partnerships that grew revenue from 7% to 30%.
Jody is the co-founder of Introhive, an AI-powered platform that transforms B2B SaaS sales through CRM data intelligence. He raised $135M+ and landed enterprise sales wins like PwC with 100K users.
🔑 Key Lessons
🏢 B2B SaaS sales depend on solving the data problem first: Introhive spent 4 years raising CRM accuracy from 65% to 90%+ because bad data killed enterprise sales retention.
🎯 Focus B2B SaaS sales on one vertical to dominate it: Introhive targeted accounting firms where they had security advantages and existing relationships.
🤝 Founders should own B2B SaaS sales before hiring reps: Jody ran every meeting for four years as founder-led selling before transitioning to a sales hire.
📉 Inbound marketing fails without brand - start outbound: A VP of Marketing from Salesforce produced zero leads because enterprise sales tactics for known brands don't transfer.
🤝 Turn customers into SaaS partnerships for B2B SaaS sales growth: Partner revenue jumped from 7% to 30% after CRM vendors realized Introhive eliminated their churn risk.
Chapters
Introduction
What Introhive does
Background and previous exits
Identifying the CRM data problem
Building the data accuracy platform
Landing PwC through enterprise sales
Founder-led selling and hiring salespeople
Challenges of early B2B SaaS sales
When to hire your first salesperson
Why inbound marketing failed early
Focusing on one vertical market
Three-year enterprise sales cycles
Growing SaaS partnerships from 7% to 30%
Board member selection lessons
Lightning round
Resources
Full show notes: https://saasclub.io/304
Join 5,000+ SaaS founders: https://saasclub.io/email
35 min
December 15, 2021Selling SaaS Without Sales Experience: $0 to $1M
Mitch Causey had no sales background when he started selling SaaS without sales experience. He ran a one-person SEO agency using spreadsheets, then turned those into software and grew DemandWell to $1M+ ARR.
Learn how Mitch built a SaaS sales process by selling SaaS without sales experience first, pre-selling software before it existed, and developing a founder-led sales playbook before hiring reps.
Mitch is the co-founder of DemandWell. His journey of selling SaaS without sales experience started with a concierge MVP and referral-driven founder-led sales that reached $150K before building any code.
🔑 Key Lessons
🤝 Selling SaaS without sales experience builds a repeatable playbook: Mitch closed every deal himself before hiring AEs, handing them a proven pitch rather than guessing.
🛠️ A concierge MVP validates faster than building software: Mitch ran DemandWell as a manual service for 18 months, proving the idea before any development spend.
🤝 Pre-sell by delivering the outcome manually: DemandWell sold contracts before the product existed, demonstrating founder-led sales at its best.
🚀 Hire an SDR before AEs when selling SaaS without sales experience: Outsourcing lead gen freed Mitch to refine the SaaS sales process and focus on closing.
💰 LinkedIn ads work when ACV justifies the cost: DemandWell's $30K average contract made LinkedIn viable, with near-100% MQL-to-qualified rates.
Chapters
Introduction
What DemandWell does and who it serves
Starting as an agency with no software plans
The 18-month concierge MVP with spreadsheets
Revenue and customer count
The people plus platform coaching model
How a non-technical founder built the product
From $0 to $150K through referrals
Selling SaaS without sales experience and pre-selling
Hiring an outsourced SDR for the SaaS sales process
Bringing on account executives
Why LinkedIn ads work at $30K ACV
Founder-led sales and scaling advice
Lightning round
Resources
Full show notes: https://saasclub.io/303
Join 5,000+ SaaS founders: https://saasclub.io/email
41 min
December 08, 2021Recurring Revenue: Triple Prices, Cut Churn to 2%
Jordan Gal built CartHook into a $6M ARR recurring revenue machine on Shopify. Then Shopify shut him down. But before that, his SaaS pricing strategy of tripling prices transformed a leaky business into a healthy one.
Discover how raising recurring revenue prices from $99 to $500 plus transaction fees achieved churn reduction from 15% to 2% and doubled MRR from $250K to $500K in one year.
Jordan is the co-founder of Rally. He previously grew CartHook's recurring revenue to $6M ARR processing $2.5 billion in GMV before platform risk forced a pivot.
🔑 Key Lessons
💰 Tripling recurring revenue prices filters wrong-fit customers: Jordan raised CartHook from $99 to $300 with zero drop in demand, achieving immediate churn reduction.
📉 High churn gets masked by strong recurring revenue growth: 400 trial signups per month with 15% churn would have capped MRR without raising prices.
🎯 Switch from self-serve to demos for recurring revenue power: Requiring applications dropped signups from 400 to 20 but attracted merchants paying $500 plus transaction fees.
💰 Raise prices on existing customers with a value promise: Jordan gave six months notice, committed to SaaS pricing improvements, and most customers stayed.
⚠️ Platform risk scales with your recurring revenue success: CartHook thrived on Shopify until processing $100M+ per month, when Shopify blocked new customers.
Chapters
Introduction
What Rally does and the headless checkout concept
The backstory - founding CartHook
The abandoned cart idea and cold email sales
No-brainer SaaS pricing that removed buyer risk
Raising funding and finding a CTO
Customizable Shopify checkout discovery
Explosive launch demand
Why tripling the recurring revenue price was right
Spotting the churn wall at $250K MRR
Requiring demos and raising prices for churn reduction
How Shopify forced CartHook to change
Platform risk lessons for every founder
Lightning round
Resources
Full show notes: https://saasclub.io/302
Join 5,000+ SaaS founders: https://saasclub.io/email
55 min
November 30, 2021Selling a SaaS Business: Buy at $500K, Sell 3x
Raj Sheth bootstrapped RecruiterBox to $4M ARR, sold to private equity, and then built a SaaS factory focused on buying and selling SaaS businesses. His first SaaS acquisition returned 3x in 13 months.
Learn how Raj evaluates SaaS companies at $1-3M ARR, turns them around with a SaaS turnaround playbook, and positions each one for selling a SaaS business at a premium. His system targets 50% EBITDA before reinvesting.
Raj is the founder of Decalab, which specializes in buying SaaS companies and selling a SaaS business after optimizing operations. Before selling a SaaS business became his focus, he grew RecruiterBox using SEO, content marketing, and paid acquisition.
🔑 Key Lessons
🎯 Selling a SaaS business starts with buying right: Raj targets companies at $1-3M ARR with low churn but stalled growth, paying sub-3x multiples on net profit.
📉 Cut costs to 50% EBITDA before selling a SaaS business: After his first SaaS acquisition of FlyData, Raj removed the founder's salary and reinvested profits into growth.
🔄 Use Crunchbase to find SaaS businesses to buy: Raj searched for companies that raised money 4+ years ago with fewer than 10 employees, booking 22 Zoom calls in 3 days.
💰 Low churn makes buying SaaS companies safer: Resilient recurring revenue gave Raj time to learn the space before turning FlyData around and selling.
🛠️ Selling a SaaS business you've improved compounds returns: Decalab aggregates 5-10 companies, moving profits between them and sharing playbooks across the portfolio.
Chapters
Introduction
What is Decalab and the SaaS factory model
Two failed B2C startups before SaaS
Co-founding RecruiterBox
Growing RecruiterBox to $4M+ ARR
Early growth channels: Google Apps, HARO
SEO as the primary growth channel
Paid acquisition economics
Attempting the move upmarket
Buying SaaS companies through Decalab
Finding targets on Crunchbase
SaaS turnaround: FlyData sold for 3x
Building the selling a SaaS business thesis
Why acquiring beats building
Lightning round
Resources
Full show notes: https://saasclub.io/301
Join 5,000+ SaaS founders: https://saasclub.io/email
48 min
November 24, 2021Starting a SaaS: 8 Founders From 6 Countries Share Lessons
What happens when eight founders starting a SaaS from Germany, New Zealand, Louisiana, San Francisco, South Africa, India, Florida, and France all share their stories? You hear what it really takes to keep going when you feel alone, broke, and unsure if anyone will ever use your product.
For the 300th episode of The SaaS Podcast, host Omer Khan invited eight listeners who are starting a SaaS to share how they found their first customers, what kept them motivated, and what lessons helped them avoid costly mistakes. These early-stage SaaS founders prove that building a SaaS is hard everywhere - and that the SaaS founder journey gets easier when you learn from others.
SquareKicker reached first six figures bootstrapped. Explorerland grew revenue 400%. Situation Hub's non-technical founder built a crisis management SaaS from scratch. TeachFloor overhauled pricing after learning from peers. Fresh Projects grew globally from South Africa. All while starting a SaaS without Silicon Valley connections.
Key Lessons
🎯 Market timing matters more than product readiness when starting a SaaS: Alexander Watson built Explorerland years before the market needed it, but revenue grew 400% when corporate transparency requirements caught up to his product.
🚀 Bootstrapped founders can reach six figures without funding: Nick and Hannah Ippolito built SquareKicker to 3,000 installs and break-even MRR within a year of launching, proving a small team with focus can compete.
🧠 Learning from others' mistakes is the fastest shortcut: Gerard Braud, a non-technical founder starting a SaaS, compensated for lack of experience by studying hundreds of founder stories - treating peer learning as a graduate degree.
💰 Pricing confidence comes from hearing how other founders handled it: Maria Bovee restructured TeachFloor's pricing after learning from peers, gaining the confidence to make changes she had been putting off for months.
🌍 Early-stage SaaS founders outside Silicon Valley build global companies: Simon Berry grew Fresh Projects from South Africa to customers worldwide, proving geography does not limit a SaaS business.
Chapters
Introduction - Episode 300 milestone
Why this episode is different
Alexander Watson - Explorerland (Germany)
Alexander's story: Forest management SaaS with 400% revenue growth
Nick and Hannah Ippolito - SquareKicker (New Zealand)
Nick and Hannah's story: Bootstrapping to six figures with three kids
Gerard Braud - Situation Hub (Louisiana)
Gerard's story: Non-technical founder starting a SaaS
Maria Bovee - TeachFloor (San Francisco)
Maria's story: Gaining pricing confidence from founder stories
Simon Berry - Fresh Projects (South Africa)
Simon's story: Building a global SaaS from Johannesburg
Cal Tiger - Shake and Send (Florida)
Cal's story: Marketing challenges for tiny SaaS companies
Vignesh Ganeshan - Press9 (India)
Vignesh's story: Strategic confidence and tactical clarity
Anise Delport - Think Tanks (France) and closing thoughts
Resources
Full show notes: https://saasclub.io/300
Join 5,000+ SaaS founders: https://saasclub.io/email
17 min
October 28, 2021SaaS SEO Strategy: The Link Building Playbook That Works
Most SaaS companies invest heavily in content creation and then do nothing to promote it. Alan Silvestri built an entire agency around fixing that SaaS SEO strategy gap - and his outreach email was so good it landed him on this podcast after Omer initially said no.
In this episode, Alan walks through his exact SaaS SEO strategy for link building and content promotion. He explains why most outreach fails, how to reverse-engineer competitor backlinks to find untapped prospects, and the SaaS content marketing process that separates companies dominating organic search from those with content graveyards.
Growth Gorilla's link building playbook distinguishes between "money pages" (keyword-targeted content) and "linkable assets" (content designed purely to attract backlinks). Alan's content promotion process uses personalized outreach that leads with genuine value rather than generic pitches.
Key Lessons
🎯 SaaS SEO strategy requires equal investment in creation and promotion: Publishing content without promoting it creates a "content graveyard." Alan says companies should invest as much time in link building as they spend on content creation.
📧 Personalized outreach gets replies, generic pitches get deleted: Alan's email to Omer stood out from thousands because it led with value and personalization. Your outreach should ask questions and offer help, not pitch your company.
🔄 Reverse-engineer competitor backlinks to find untapped prospects: Instead of contacting the same sites linking to competitors, analyze what types of pages link out. Then find similar pages not linking to anyone yet for better SaaS SEO strategy results.
💰 Separate money pages from linkable assets in your content strategy: Money pages target keywords and drive conversions. Linkable assets like infographics attract backlinks. Use both to build domain authority that lifts all your content.
📉 SaaS SEO strategy results are exponential, not linear - do not quit early: Most companies see 20% of results after 80% of effort and give up. Committing long-term separates companies that dominate organic search from those with content graveyards.
Chapters
Introduction
Alan's favorite quote: Marty McFly from Back to the Future
What Growth Gorilla does: content promotion for B2B SaaS
Why content promotion matters for SaaS companies
The content graveyard: why most SaaS content never ranks
Common SaaS SEO strategy mistakes
How Alan's outreach stood out and led to this podcast
The skyscraper approach and why it stopped working
Reverse-engineering competitor backlinks for untapped prospects
Money pages vs. linkable assets in SaaS SEO strategy
Building a prospect list and finding the right contacts
How to prioritize which pages to promote first
Combining Ahrefs data with Google Analytics conversions
Creating a 12-month content marketing roadmap
The outreach email that actually gets replies
Personalization at scale: tools and processes
Follow-up strategy: value first, ask second
The exponential curve of SaaS SEO strategy results
Lightning Round
Wrap Up
Resources
Full show notes: https://saasclub.io/299
Join 5,000+ SaaS founders: https://saasclub.io/email
56 min
October 20, 2021SaaS Go-to-Market: One Niche Built a $20M Business
Dave MacLeod spent years trying to sell to everyone and got nowhere. Then he focused his SaaS go-to-market on one niche SaaS market - school districts - and that single decision built a $20M business.
For almost five years, ThoughtExchange focused exclusively on K-12 education. That SaaS go-to-market discipline gave them sharp messaging, passionate customer advocates, and a product purpose-built for one buyer. Today, half their business comes from Fortune 100 enterprise customers - but only because they committed to vertical focus before going wide.
Dave's go-to-market strategy proves that niche SaaS focus creates the foundation for broad expansion. ThoughtExchange grew to $20M ARR with 200 employees and $45M in funding by resisting the temptation to chase every market opportunity.
Key Lessons
🎯 SaaS go-to-market focus on one market is how you find product-market fit: ThoughtExchange tried selling to everyone and failed. Focusing exclusively on school districts for 5 years built a $20M ARR business with passionate customer advocates.
📉 Building a product before finding a problem is the classic mistake: Dave and Jim created collective intelligence software first, then wandered looking for buyers. They heard "interesting but not for us" repeatedly until finding education.
🏢 Niche SaaS discipline creates the foundation for enterprise expansion: ThoughtExchange built product depth and customer references in education that made Fortune 100 sales possible. Half their revenue now comes from corporate enterprise.
💰 Stay in your market until customers recruit for you: Dave says you have not found product-market fit until 10 customers voluntarily take reference calls, go on stage, and help you sign up others in the same market.
🧠 A billion-dollar company grew by doing 80% less, not more: A CEO with nearly $1B in revenue told Dave the same SaaS go-to-market truth - focus is critical at every stage, not just the early days.
Chapters
Introduction
Dave's favorite quote: good judgment comes from experience
What ThoughtExchange does: discussion management for large groups
Origin story: the outdoor guide and the physicist
Business size: $20M ARR with 200 employees and $45M raised
The "terrible" mistake of building product before finding a problem
Recipe cards and infinite recipe cards: how the idea was born
Struggling to find customers: "interesting but not for us"
The school superintendent who changed everything
Going all in on one niche: SaaS go-to-market with school districts
Why niche focus works: customers become advocates
When to know you are in the right market
The temptation to expand too early
Investor pushback on an education focus
Building vertical-agnostic features inside a niche market
Expanding from education to corporate enterprise
The billion-dollar CEO who grew by doing 80% less
How half the business now comes from Fortune 100
Lightning Round
Wrap Up
Resources
Full show notes: https://saasclub.io/298
Join 5,000+ SaaS founders: https://saasclub.io/email
46 min

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

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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.